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$200 per night *
Sunshine Luxury Suite with 2 Free Bikes & Garage

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foli......

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  • Pet Friendly
  • Non Smoking

$1700 - $3625 per week *
Artist Garden

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along wi......

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  • Non Smoking

$1000 - $2200 per week *
2br - Best Old Town Location

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck....

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  • Non Smoking

$1300 - $1950 per week *
Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access t

Max Guests: 4Bedrooms: 2Bathrooms: Type: CondoLocation: Key West
Billy's Blue Heaven is brand new to the vacation destination rental market in December 2011. This means it is fresh, clean and pristine. Only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex's lush l......

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  • Non Smoking

Tropical Retreat

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CottageLocation: Key West
Lush gardens surround this lovingly restored two-story Bahamian house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropic......

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  • Non Smoking

$1300 - $2610 per week *
2 br Key West Condo Vacation Rental

Max Guests: 5Bedrooms: 2Bathrooms: 1.5Type: CondoLocation: Key West
LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on the 2nd floor. Downstairs is an open floor plan with kitchen/dining room/living room and half bath. French doors from li...

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$265 per night *
2 Bed / 2 Bath Luxury Condo on the Ocean - Sleeps 6 (next to Smather'

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Beautifully remodeled, 1374 sq. ft., 2 bedroom (King Beds) 2Bath luxury condo located on the beach - SLEEPS 6. Gorgeously landscaped & located right next door to Smather's Beach, the largest & best beach in Key West! Kitchen & wetbar both f......

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  • Handicap Accessible
  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$1600 - $3408 per week *
Villa Soleil

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
VILLA SOLEIL -- Located in the historic Foundry building of Truman Annex, a beautiful gated community in the heart of Old Key West, Villa Soleil is the ideal vacation getaway if you are looking for relaxation and an ideal walking location to all t......

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  • Non Smoking

$3000 - $5000 per month *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighbo...

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$180 per night *
4br - Harbor Walk hideaways

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: CottageLocation: Key West
Daily price varies by number of units, season, and length of stay. Lowest prices shown above. Private compound right in the heart of old town. 1 minute or less from Schooner Wharf with all the water activities imaginable; Sloppy Joe's and Conch Republic (with some of the best music on the rock) and close to all of Old Town. 2 One BR units and one 2BR unit rent separately or together (which makes t...

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  • Non Smoking

Key West Rental (Casa De Suenos) House of Dreams!

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Casa de Suenos, an English Dream house that is Delightful in every way. This hidden gem was completely re-done as a custom upscale condo, with the finest amenities and is located in the Meadows area of Old Town Key West on Pearl Street. This is a ......

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  • Pet Friendly
  • Non Smoking

$4000 - $5250 per month *
'Mango Gardens' Charming, Walking Distance to Duval, and Historic Seap

Max Guests: 8Bedrooms: 4Bathrooms: Type: HomeLocation: Key West
Mango Gardens is a charming historic remodeled home located in Old Town, Key West. Private and spacious home has hardwood floors thru out. The first floor features a large fully equipped kitchen, dining area and the living area opening through Fre......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$4000 - $6500 per month *
Private Luxury in Casa Marina Neighborhood

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
The Casa Marina neighborhood is one of the most coveted residential areas in Historic Old Town Key West. Known for outstanding architecture and glorious private gardens, many homes in the area are considered the “cream of the crop” of Key West, a......

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  • Non Smoking

2br - Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This is a Non-Smoking Condo/Hotel You May Smoke on Balcony, Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped ...

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is located one block from the world famous Duval Street. This stunning second floor, one bedroom one bath condominium is filled with quality, style and class throughout. The lavish kitchen offers custom cherry wood cabinets with tasteful granite countertops and high end Kitche...

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  • Non Smoking

$210 - $413 per night *
Key West Ginger House

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
KEY WEST GINGER HOUSE - An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants blooming in our tropical paradise. Key West Ginger House offers 2 bedrooms and 2 full baths ensuite. This......

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  • Non Smoking

$2800 - $3600 per month *
'CONCH CASITA 2 @ ELIZABETH': Charmingly Renovated 2BR/1BA Old Town Co

Max Guests: 3Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
This wonderful little cottage is the sister to 'Conch Casita 3' and 'Conch Casita 4' and is right next door. Located on 720 Elizabeth Street, a quiet one-way lane, this home is set 100 feet back in its own little tranquil world. When you first lay......

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  • Pet Friendly
  • Non Smoking

Truman Annex Best Location it Town

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Greetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita. ''Margarita Villas'' are located in historic Old Town in a beautiful, very private gated c......

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  • Non Smoking

$6600 - $14000 per month *
“PENTHOUSE @ THE STEAMPLANT': Luxurious 3BR/3.5BA Condo w/ Private Poo

Max Guests: 8Bedrooms: 3Bathrooms: 3.5Type: CondoLocation: Key West
There is nothing else like this home in all of Key West: Card-only access to your assigned spaces in the parking garage, a private elevator that opens into your own 3000 square foot condo, window walls throughout the home, private roof terrace wit......

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  • Pet Friendly
  • Non Smoking

3 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Just 10 miles from Old Town you?ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then cook some of the catch out on your deck with a few cold ones. And while the sun sets, you could always count on seeing a couple of manatees hanging out by...

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  • Non Smoking

$1260 - $2240 per week *
1 br Key West Cottage Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound just one half block off Duval Street next to The Curry Mansion between Duval and Simonton Streets. Ann Street is close to the Historic Seaport for casual dining and water sports activities, Sunset Piers and all the activities of Duval Street including Sloppy Joes, Hogs Breath and ...

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$4000 - $8800 per month *
'PARADISE PERFECTED @ THE SANCTUARY': Elegant 3BR/2.5BA Luxury Home...

Max Guests: 8Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
Choosing a vacation home is always a challenge. It sometimes seems like the owners have decorated the home with the best that the discount stores had to offer, and then let it ride for as many years as possible. Well, this is not the case with “Pa......

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  • Pet Friendly
  • Non Smoking

Hollinsed House - Key West Old Town - Great Location!!

Max Guests: 2Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
Beauty and economy in the heart of Old Town Key West! Ideally located just one block from famous Duval Street, this ground floor studio suite is equipped to make your stay in the islands comfortable and convenient. This charming suite is comforta......

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  • Non Smoking

$340 - $682 per night *
Amelia Home

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one......

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  • Non Smoking

3br - Captain #039;s House

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
This Historic Register property enjoys a superior location in the Heart of Old Town - an easy 4 block walk from historic Duval Street, the center of Key West’s vibrant night life and 3 blocks from The Bight harbor. It is located at 522 Margaret Street between Southard and Fleming Streets 2 doors from Michael’s Restaurant and a half block from Mangia-Mangia, two of Key West’s most popular restauran...

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  • Non Smoking

'Aqui Su Casa En Key West' is 'Your Home Here in Key West'

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Located in the Casa Marina neighborhood of Key West, it’s within walking distance (3-5 blocks) of Key West’s nicest beaches (including South, Dog, Higgs & Rest beaches), the White Street Pier (the true Southern Most Point of the United States) and......

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  • Non Smoking

$400 - $450 per night *
Pelican Landing St.John Retreat

Max Guests: 10Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

Captain's Hideout in Key West

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: VillaLocation: Key West
Freshly redone, completed January 2009. Brand new high end furniture, including leather sofa and love seat. Brand new Beds, top of the line mattresses, and all the fluffy bedding. This is a very clean, private, gated and fenced compound. Priva......

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  • Pet Friendly
  • Non Smoking

$140 - $165 per night *
The Red Grouper - A Funky Floating Condo with Direct Ocean Access

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: Location: Key West
The Red Grouper is a one bedroom, one full bath floating house located at Stock Island Marina Village. With direct access to the Atlantic Ocean, it's the perfect way to experience Key West by water. Bring your boat and tie up to the Red Grouper, o......

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  • Pet Friendly
  • Non Smoking

$198 - $268 per night *
0br - Bone Island Vacation Rentals Little Palm

Max Guests: 2Bedrooms: Bathrooms: 1Type: CottageLocation: Key West
LITTLE PALM - What an idyllic setting! Picture a new cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off by the marble floors and the small mini kitchen; refrigerator, coffee maker, drink blender, toaster, and microwave makes relaxing in your own private hot tu...

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Eaton Manor sits on the north side of LaBrisa and provides easy access to Smathers beach, where you can sail, boat, kiteboard, parasail, walk, run, roller blade and witness the most beautiful morning sunrise. Though Eaton Manor is only seconds away from all the daytime action, Eaton Manor provides peaceful and quiet serenity at night. Relax on the balcony overlooking the salt pond, where beautiful...

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  • Non Smoking

$260 - $420 per night *
Pete's West Cottage

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. ......

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  • Non Smoking

$195 - $295 per night *
Bargain Rates in Truman Annex - Heart of Old Town, Key West

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh paint throughout, all tile flooring, and brand new designer furnishings make this a home away from home. A large r......

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  • Non Smoking

Ocean View- Key West Condo

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Discover paradise of Key West in a distinctive setting. Luxury, two-bedroom, two-bath, (sleeps 4-6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is decorated in authentic island tradit......

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  • Non Smoking

$1600 - $3190 per week *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
ISLAND SPICE -- A lovely 2 bedroom, 2.5 bath townhome, located in the historic Foundry building of the prestigious Truman Annex community. The brick exterior, and the brick interior wall of the living room provide you with an Old Town cozy feel, yet this newly updated home has a trendy tropical flair. On the first floor, there is the living room, kitchen and one-half bathroom. From the living area...

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$2400 - $4200 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL A spacious one bedroom in a four condominium building in the Casa Marina District of Key West. The cool, classy decor and white wicker furniture give this apartment a truly tropical feel. Walk from your gourmet equipped kitchen onto a large deck complete with outdoor dining furniture and gas grill. This deck overlooks the pool with spa and gardens. Bedding: 1 king, 1 sleeping...

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$11000 - $12800 per month *
Casa Del Aquabella

Max Guests: 10Bedrooms: 4Bathrooms: 3.5Type: HomeLocation: Key West
Art Deco Dream! Key Haven, open water views & canal front home. Totally private on two lots, this unique ground level masterpiece has it all. Extensive balconies surround the home with four Bedrooms and four and one half Bathrooms, pool, glorious ......

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  • Non Smoking

Small Family Holiday Complex, ideal for kids and adults of all ages

Max Guests: 6Bedrooms: 3Bathrooms: Type: CottageLocation: Key West
Bellefontaine Park is family run park, located within the beautiful region of Normandy, surrounded by miles of infamous French countryside. The idyllic location makes this the ideal holiday destination for those who wish to enjoy the peace and tra......

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  • Non Smoking

$1200 per night *
Casa Aqua

Max Guests: 10Bedrooms: 5Bathrooms: 4Type: VillaLocation: Key West
Virtual Tour: Tour 1 Casa Aqua is a Spanish Mediterranean estate. The mansion, which can be rented separately or with the adjoining honeymoon cottage, consists of 5 bedrooms and 3 1/2 luxury baths. The state-of-the-art kitchen is a true cu......

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  • Handicap Accessible
  • Non Smoking

$2450 - $5110 per week *
Villa Paradiso a Peaceful Private Retreat

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: VillaLocation: Key West
Located in a quiet, tranquil and charming residential area, 4 blocks (5-10 min walk) from the beaches on the south of the island, and a 5-minute drive (10 minute bicycle ride) from old town (Duval Street) Villa Paradiso is a delightful 3-bedroom/......

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  • Pet Friendly
  • Non Smoking

$1295 per week *
$185 A Day Stay Above the Sea 3BR/3BA cool A/C full kitchen large li

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: YachtLocation: Key West
Why stay in a boring expensive hotel, this is the best deal in Key West. Have your own private yacht with 3 bedrooms and 3 baths, stay above the sea. A real true up close breathtaking view, breath in the clean ocean salt air. Feel the Atlantic Oce......

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  • Non Smoking

Walking to everything, Close to Beach, Old town

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
DUPONT RETREAT is a bright and spacious 3 bedroom, 3 bath home has the best of everything with a private pool surrounded by lush foliage and an extensive deck area with covered pavilion for outdoor dining. The large living room has 3 sets of glas......

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  • Non Smoking

$210 - $413 per night *
2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
KEY WEST GINGER HOUSE - An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants blooming in our tropical paradise. Key West Ginger House offers 2 bedrooms and 2 full baths ensuite. This historic home built in 1933 takes advantage of every breeze with plenty of windows, French doors, high ceilings and wood floors. Kitchen opens to the liv...

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  • Pet Friendly

***Steps from Duval $79-$129 Night - Free Bikes Included!!!***

Max Guests: 2Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
Looking for the perfect affordable hide-away in Key West? Located in a remodeled Victorian Home - this guest room is just perfect for two! This guest room is cozy with a queen size bed but is so much better than a hotel room. We provide high qual......

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  • Non Smoking

Key West luxury art deco style oceanside condo with pool and beach

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This condo is one of the best 1800 Atlantic has to offer. Situated on the Atlantic Ocean in a tropical setting with lush landscaping, this condo boasts resort style amenities. A 400 foot beach, Olympic size heated pool, large jacuzzi, sauna, light......

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  • Handicap Accessible
  • Non Smoking

$470 - $800 per night *
4 br Key West Home Vacation Rental

Max Guests: 10Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
Welcome to the Beach!!!! No this house isn't oceanfront! But in Key West almost anything is possible. This house has just been transformed into a relaxed beach house with many updates & upgrades. New furniture, cabinets and appliances as well as a redecorating of everything including the garden to make this a great vacation show place. Enter the house with gingerbread touches on the exterior to se...

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$210 - $392 per night *
Island Pearl

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
ISLAND PEARL: True island living in this 1 loft bedroom 1 bath cottage, complete with living room and kitchen. French doors open to a meandering deck surrounded by tropical foliage. This secluded hideaway is located behind a needlepoint store i......

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  • Non Smoking

$2500 - $3500 per month *
Historic Tropical Beauty

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
Beautiful open bedroom with wood floors overlooking downstairs & view of the garden also 2 bedroom with upstairs deck or can be combined. Large bathroom & shower with dual shower heads, custom walk in closet, Full living area with Queen Size Day......

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  • Non Smoking

2br - The 2 Bedroom Deluxe Poolside Villa

Max Guests: 7Bedrooms: 2Bathrooms: 2Type: VillaLocation: Key West
Villas Key West is a small (7 unit) guesthouse located 200 feet from Duval Street! Our accommodations are apartments set in 2 old historic Key West houses joined by a deck and temperature controlled pool. The very heart of Old Town Key West within easy walking distance of everything. There is no better location in Key West… The 2 BEDROOM DELUXE VILLA was completely gutted and renovated in 2007. No...

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  • Non Smoking

$6499 per month *
Key West luxury beachside w/ all modern ammenities

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This is one of the best units at 1800 Atlantic Condominiums. You feel as though you are deep in the Caribbean with the tropical oceanfront setting this condominium is set on. Situated on the Atlantic Ocean & steps from Smathers Beach. This design......

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  • Non Smoking

$140 - $165 per night *
The Green Turtle - A Funky Floating Cottage with Direct Ocean Access

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: Location: Key West
The Green Turtle is a 1 bedroom, 1 bath floating house located at Stock Island Marina Village. With direct access to the Atlantic Ocean, it's the perfect way to experience Key West by water. Bring your boat and tie up to the Red Grouper, or just ......

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  • Non Smoking

$1350 per week *
Harbor Inn Condominium, Charming, quiet, elegant, beautiful, modern, l

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
A beautiful, charming two bedroom, two bath condominium in an historic Key West home. No non-descript apartment building here. This is definitely the type of place you would like to live in and not just stay in. The property comes fully furnished, ......

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  • Non Smoking

$6500 - $12000 per month *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL New property to our rental program! Villa Martinique is luxurious, tropical and tasteful! Located down a quiet lane, 2 blocks to the center of Duval Street, and walking distance to the best restaurants, shopping, galleries and entertainment Key West has to offer is this exceptional property. If you find that you and your family search for the best in quality, location, and pr...

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$2800 per week *
Monthly Rates-KW living at its finest-quiet neighborhood, near duval a

Max Guests: 10Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Well maintained recently renovated luxury home with heated pool in very private yard. This charming home was built in 1918 so it has historical charm with high wood ceilings and Cuban tile accents on the front porch and in a guest bath, yet it ha......

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  • Non Smoking

South St. Cottage

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A larg......

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  • Non Smoking

Petronia Palms, Just Off Duval St. and Has a Large Pool!

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple rentals. Petronia Palms Is located just one block from the famous “Duval Street”! This lovely stand alone 800 sq. ft. cottage is located on Petronia Street Rear off th......

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  • Pet Friendly
  • Non Smoking

$4500 - $10500 per week *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
In the fabulous Truman Annex enclave and near the Caroline Street walking gate directly to downtown Key West, this nicely decorated home features a thirty foot pool with waterfall, expansive decks and extensive tropical landscaping for privacy and outdoor enjoyment. Inside an enormous living/dining area is surrounded by french doors that afford special indoor/outdoor "Key West" lifestyle with a be...

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$149 - $179 per night *
Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beac

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
For nearly 15 years now guests have been delighted to discover the Beach Bungalow-Key West. Nestled among palm trees, hibuscus, and boganvillas, the Beach Bungalow is located in a compound just a block from the Beach and Atlantic Ocean, about a m......

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  • Non Smoking

$4000 per month *
Turquoise Mermaid ~ Old Town Key West

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
VACATION... like a local in Old Town Key West just a few short blocks from the Historic Seaport area where you will find waterfront restaurants and quaint shops. This ground floor unit is conveniently located near the sunny swimming pool and off......

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  • Non Smoking

$1500 - $2900 per week *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in prestigous Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora or wander just a few block over to all the excitement of Duval Street. Deco...

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$1800 - $2200 per week *
2br - A Touch of Bermuda in Key West

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CottageLocation: Key West
Here is why people call this the best value in Key West. This Bermuda-style cottage is my vacation home so you will find it is kept in impeccable condition. Everything and anything you'd want to do is within walking distance. This includes the best beach in Key West, Ft. Zachary Taylor State Park or Duval Street with its wonderful restaurants, unique shops, creative art galleries, lively bars, baw...

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  • Non Smoking

$550 - $864 per night *
Paradise Harbor Retreat

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Keys style, this spacious townhome has 3 bedrooms, 3.5 baths and is situated in a quiet Meadows reside......

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  • Handicap Accessible
  • Non Smoking

$112 - $228 per night *
Simonton Studio, an Old Town get-away for 2. New Pricing

Max Guests: 2Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
This Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everything you need to fix your ......

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  • Non Smoking

$3000 - $5000 per month *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your ocean view or natural water sanctuary view balcony. This residential condominium is situated opposite the largest beach on our tiny island of Key West, Smathers's Beach, while offering many amenities of a resort hotel. Sunbathe next to a large kidney-shaped pool, with beautiful, tropical landscaping. Soak in the adjac...

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$520 - $800 per night *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
This property has it all! This award winning renovation offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room has a spiral staircase to the ...

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$1150 - $1900 per week *
Nassau Suite - Old Town Key West Villa

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: VillaLocation: Key West
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upsta......

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  • Non Smoking

3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
The first floor includes a front porch, bedroom, completely remodeled kitchen, remodeled lower bathroom, large open living area, and beautiful French doors leading to a private deck and backyard. The backyard includes a table for six and new gas grill.The property is located within the renowned Truman Annex Shipyard community. There is a guarded gatehouse and secured entrance to a private parking ...

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  • Non Smoking

$500 - $550 per night *
Pelican Landing St. Thomas Retreat

Max Guests: 14Bedrooms: 4Bathrooms: 4Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$470 - $800 per night *
Louisa House

Max Guests: 8Bedrooms: 4Bathrooms: 3.5Type: HomeLocation: Key West
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom......

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  • Non Smoking

$450 - $873 per night *
3 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
BAHAMA DREAMING: A beautifully renovated Conch house conveniently located in the center of Old Town, one block behind celebrated Duval Street, this cottage in Key West is quiet and private. Only a short walk to the many attractions, Key West activities, world-renown Key West restaurants and nightclubs, historic seaport area, and the many specialty shops that make Key West a tropical island paradis...

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  • Pet Friendly

$2100 - $2800 per week *
Private Key West Weekly Vacation rental in the heart of Old Town

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
The Pineapple Cottage is a weekly vacation rental that offers what everyone wants: A great location and total privacy! Surrounded by a tropical garden, the Pineapple Cottage is located between Duval & Simonton Streets and is totally private. There......

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  • Non Smoking

$3500 - $6500 per month *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL ALBURY BUNGALOW A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, one bathroom house also boasts a separate cottage bedroom with it's own bathroom. Lounge on the sunny deck around the heated pool or relax in the comfortable combined living/dining room. Nicely furnished with many unique antique pieces with tropical...

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$5500 - $11760 per week *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block away from Duval and Mallory Square. Covered porches overlooking private swimming pool. Beautiful hardwood and tiled floors with high ceilings and lots of ceiling fans. This home has 4 bedrooms (all Queen) and 4 baths and is called Bloom'n Paradise. It can be rented in conjuncti...

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$3200 - $5100 per month *
Newton Street Hideaway

Max Guests: 2Bedrooms: 1Bathrooms: 2Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle ......

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  • Non Smoking

$345 - $531 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
KEY WEST CROWN JEWEL -- We know that you will enjoy staying in our little bit of Paradise. This is a 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space and vaulted ceilings. Enjoy absolutely breathtaking ocean views and the colors of the sunset from the 35-foot balcony, as well as from both bedrooms and the living room. Upgraded appointments include WIFI internet access...

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2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights, light tile floors and loads of french doors leading from the living room & both the bedrooms to the pool area create a real indo...

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$220 - $381 per night *
Papaya Place

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
PAPAYA PLACE pops with color! This great 2 bedroom 2 bath condominium at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from th......

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  • Non Smoking

$270 - $400 per night *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this two bedroom cottage. Step from your porch on to a bricked walkway leading to a spacious outdoors feat...

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  • Pet Friendly

$150 - $200 per night *
Pelican Landing Antigua Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$220 - $381 per night *
Florida Palm

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
FLORIDA PALM: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and suns......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$328 - $478 per night *
Isla Bella-A Gorgeous Tropical Oasis with Parking & Jacuzzi

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
The 9' ceilings in our custom designed Isla Bella will add to your feeling of comfort and relaxation during your visit. This house has an off street parking space as well as a private Jacuzzi. There is a front porch and two side decks with gas gri......

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  • Non Smoking

$1600 - $3190 per week *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
VILLA SOLEIL -- Located in the historic Foundry building of Truman Annex, a beautiful gated community in the heart of Old Key West, Villa Soleil is the ideal vacation getaway if you are looking for relaxation and an ideal walking location to all the best Key West has to offer. Your entry through a white gated fence, opens to a private brick courtyard lush with palm trees and brightly flowering tro...

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Annex Luxury - Location and Classic Key West Charm

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Classic Key West charm and great location within the Truman Annex gated community make this home of distinction an ideal place for that tropical getaway that you have always dreamed about. We have the most comfortable bedding in Key West which m......

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  • Pet Friendly
  • Non Smoking

$4500 - $7000 per month *
'TROPIC OASIS @ THE SANCTUARY': 4BR/3BA Home + Private Pool in Quiet C

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: CottageLocation: Key West
The first floor of this tropical style home is open and spacious: there are windows everywhere you look. The living room has plenty of room for everyone to relax. Just off the living room, there is a private study with a queen sized convertible so......

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  • Non Smoking

Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 bedrooms, 2 full bathrooms, sleeps 6, wireless internet access...

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

The Kaleidoscope - an elegantly colorful Key West home.

Max Guests: 8Bedrooms: 4Bathrooms: 4.5Type: HomeLocation: Key West
Elegant Key West vacation home with room for family and friends. Surrounded by a high wooden fence for privacy this classic 2 story offers outdoor areas perfect for enjoying the island weather. Beautifully landscaped with lush mature vegetation an......

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  • Non Smoking

'The Frances House' Old Town Key West

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Frances House is a beautifully designed & decorated 3BR/3BA turn of the century Conch House located in the Heart of “Old Town” Key West, Florida on Frances St. Careful detail care has been taken on this total design winning renovation. Extremely......

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  • Pet Friendly
  • Non Smoking

$168 - $248 per night *
0br - Bone Island Vacation Rentals Palm Isle

Max Guests: 4Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
Palm Isle - a room ahead of its time - A truly "green unit". Your room mate or in this case "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private Jacuzzi and treetop hammock. The second-story studio "sweet" comes complete with mini kitchen (no stove), microwave, fridge, sink and all the tools for preparing drinks and snacks. The spacious suite has a King bed, ...

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 3.5Type: CondoLocation: Key West
Located at the Key West Golf Course in the sancutary is this 2 bedroom 2 1/2 bathroom multilevel spa home. The outside private patio is wonderful for a morning paper and a dip in the spa. The home is beautifully decorated with an open floor plan for the living, dining room, and kitchen area. Upstairs are 2 bedrooms each with their own bathroom. The master has access to it's own balcony. The home c...

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  • Non Smoking

$1300 - $2610 per week *
Conch Condo

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
CONCH CONDO -- This two-bedroom, two-bath condo was remodeled and completely refurnished in 2005. This second-floor unit features fully equipped kitchen, two full baths, top-quality custom furniture, plasma televisions and home theatre in living......

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  • Non Smoking

$1200 - $2000 per week *
Villa Fleur, Elegant Truman Annex condo in Old Town

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Villa Fleur is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach bea......

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  • Non Smoking

$300 - $350 per night *
Pelican Landing Aruba Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1400 - $2750 per week *
Key West vacation townhouse rental in the Truman Annex

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Attractive tropical conch style 2 story Presidents Walk townhouse on Southard St within the prestigious Truman Annex in Old Town. Three blocks to Duval St restaurants and entertainment. A short walk to Zachery Taylor beach. Downstairs is a large ......

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  • Non Smoking

$300 - $350 per night *
Pelican Landing Andros Retreat

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

Petronia Palms, Just Off Duval St. and Has a Large Pool!

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple Properties in Key West. Petronia Palms Is located just one block from the famous “Duval Street”! This lovely stand alone 800 sq. ft. cottage is located on Petronia Stree......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$300 - $350 per night *
Pelican Landing Harbor Island Retreat

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$2000 per month *
Walk to the beach!

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: ApartmentLocation: Key West
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this studio apartment is minutes from everything on the island. No cars are necessary, bikes and beach chairs are pro......

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  • Non Smoking

$210 - $380 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or barbeque in the shade of this beautiful garden. When you are done relaxing by the pool,...

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$185 - $235 per night *
2br - Island Wind Tropical Old Town Hideaway

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: TownhouseLocation: Key West
"Island Wind" welcomes you to a sun drenched oasis in the heart of Old Town. Charming Bahamian style townhome with tin roof and white spindled porches reminiscent of Old Key West Just a block off Duval Street at the corner of Truman & Simonton in Windward Park a gated community consisting of 13 privately owned homes around a 20 x 60 ft. pool. Within walking distance of all the attractions and nigh...

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  • Non Smoking

3 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area is in between the house and the cottage. The main house has hardwood floors throughout. Some of the ...

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  • Non Smoking

$4500 per month *
Quiet waterfront condo with boat slip, beach and pool! One of a kind!

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Beautiful condo centrally located in Key West. Huge master suite overlooking beach and pool. Second bedroom has private entrance. First floor walk out to beach and dock. 25 Foot boat slip available for additional fee. Stay in this wonderful condo ......

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  • Non Smoking

$3000 - $4000 per month *
The Tree House - an authentic Key West experience.

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
If it is character you are seeking you have found your accommodations. This unique space occupies the entire 2nd floor of a historic conch home on the 600 Block of Fleming Street, just 1 1/2 blocks off Duval Street and in the heart of Old Town.......

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  • Non Smoking

$4000 - $5333 per month *
Seaport House

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Located in Old Town, this home is conveniently located within walking distance to the Seaport, restaurants, and major attractions. The house has 2 bedroom 2 bath and a nice backyard with a pool. This home is cared for by a locally-based property m......

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  • Non Smoking

$350 - $530 per night *
Beach Club #108

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This elegant 3 bedroom/ 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. The u......

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  • Non Smoking

The Village Rooster

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Old Town Key West home just blocks from the famous Southernmost Point, Hemingway House, Duval Street, Lighthouse, Beaches & more. This home greets you with a charming front porch. Open living area and spacious kitchen plus two bedrooms and 2 fulls......

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  • Non Smoking

$5500 - $11760 per week *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Amazing, sophisticated home in the fabulous Truman Annex enclave. You can't beat an Admiral's Lane address in Key West. So near the Caroline Street walking gate with it's proximity to Kelly's and the nightlife of Duval, but yet tucked away at the end of a quiet residential lane. This exquisitely decorated home features a thirty foot pool with water fall, dual level decks and mature tropical landsc...

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$1820 - $3360 per week *
2br - Beach Club #104

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Welcome to unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful tropical flare. It features a huge oceanfront balcony accessed from both the living/dining area and master bedroom with very nice furnishings. It features central heat/air, cable TV, washer/dryer, well- equipped kitchen, and security entry...

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$1800 - $2100 per week *
'AZURE MORNING' @ OCEANSIDE MARINA': Lavish 3BR/2BA Oceanfront Condo +

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Imagine waking up every morning to the sun rising over the azure blue Atlantic Ocean. That's what you will experience with this beautifully furnished three bedroom condo right on the ocean at Oceanside Marina. With direct views of the ocean from t......

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  • Pet Friendly
  • Non Smoking

The Best 2 BR Truman/Shipyard, Fort Zach Beach, Mallory, Duval

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Fantastic 1st floor (garden level) condo in the best location in Key West! Holiday Dance is an end unit (extra windows and light) in the most desired row in Shipyard. Shipyard is the place to be - it is within a stone's throw of all that Key Wes......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$225 - $275 per night *
Coral Hammock 34

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Coral Hammock is one of the newest gated communities with 55 luxury resort homes with a lavish Clubhouse, Pool and lushly landscaped grounds. These custom single family homes recall the romantic charm of old Key West with spacious floor plans, vau......

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  • Non Smoking

1 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
Coconut Mallory Resort and Marina by Kees Vacations 1 bedroom/1 bathroom premium condo Bedding Configuration: Unit bedding varies. Unit sleeps 4. Unit Description: This is a 1 bed/1 bathroom condo that features a full kitchen, washer/dryer and flat panel TV with a newly refurbishment and decorated in an island inspired elegance. The unit also has private balcony, access to both resort pools, and t...

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  • Non Smoking

'Tropical Splendor' 3Bd/2Bth luxury condo & ocean view at King's Point

Max Guests: 7Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Oceanside Condos at King's Pointe Marina is one of the most prestigious communities which offers breathtaking water views and large, breezy open units. The amenities include a community pool and barbeque stands by the waters edge. Boat dockage wit......

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  • Pet Friendly
  • Non Smoking

$300 - $350 per night *
Pelican Landing Florida Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1300 - $1950 per week *
Truman Annex: Flamingo Beach Self Catering Beautiful Ground flr condo

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
'Flamingo Beach' is a beautiful ground floor condominium located within the prestigious gated community of 'Truman Annex' in Key West's 'Old Town' area. This home has a large deck area which is accessed by a set of French Doors and comes complete ......

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  • Non Smoking

$2610 - $4200 per month *
Suite Caroline - Splendor

Max Guests: 2Bedrooms: 1Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed res......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
7 night minimum rental. Paradise is definitely found in this Non-Smoking, first floor end unit condo only two short blocks off of "happening" Duval Street in Old Town Key West. Located in the upscale, gated community of Truman Annex, paradise is yours for the asking whether it's enjoying a quiet evening sipping margaritas and dining alfresco on the large deck surrounded by a tropical garden - or s...

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  • Non Smoking

Truman Annex (Gated 4BR's/4Bath's-private Pool)

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block away from Duval and Mallory Square. Covered porches overlooking private swimming pool. Beautiful hardwood and tiled floor......

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  • Non Smoking

$2610 - $4200 per month *
Suite Caroline - Ginger

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed res......

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  • Non Smoking

$1372 per night *
Casa Aqua

Max Guests: 12Bedrooms: 6Bathrooms: 4Type: VillaLocation: Key West
Virtual Tour: Tour 1 Casa Aqua is a Spanish Mediterranean estate. The mansion, which can be rented separately or with the adjoining honeymoon cottage, consists of 5 bedrooms and 3 1/2 luxury baths. The state-of-the-art kitchen is a true cu......

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  • Handicap Accessible
  • Non Smoking

$5000 - $7500 per month *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our town, the Oliva cottage has the best of everything. Amenities include driveway parking, central air co...

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  • Pet Friendly

$160 - $250 per night *
1 br Key West Ocean View Home Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
A spacious studio apartment and large deck make this the perfect romantic getaway, feast your eyes on the breathtaking views of the Atlantic Ocean. Enjoy complete privacy, bird watching, sun and fun, located next to the White Street Pier and nestled between Higgs Beach and Smather's Beach. The living room area features ceiling to floor glass windows overlooking the Atlantic Ocean, a full size kitc...

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$129 - $499 per night *
2br - The Paradise Island At The Bahama House

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Paradise Island Suite is complete pack of entertainment . Tall windows and high ceilings gives the large , two bedrooms unit brightness and comfort to feature enjoyable stay . Newly renovated , Paradise Island accommodated 6 guests comfortably . It offers furnished bedrooms along with two full sized beds & second bedroom along with queen. Living area offers futon for some sleeping space . Each roo...

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  • Non Smoking

$8500 per week *
6 bedroom Compound w/ Pool, Hot Tub, Parking & Huge Roof Deck on Duval

Max Guests: 14Bedrooms: 6Bathrooms: 7Type: VillaLocation: Key West
Perfect location and great for entertaining! In the heart of Old Town Key West across from Margaritaville and just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated pools, endl......

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  • Non Smoking

$310 - $490 per night *
3 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
In the heart of Old Town, convenient to everything. The condo is set above a brick, tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone walkup buildings in the Duval Square complex. You enter a large open living, dining, kitchen area with french doors & porch overlooking the courtyard below. The master bedroom with ensuite bath has...

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PET FRIENDLY COTTAGE

Max Guests: 4Bedrooms: Bathrooms: 1Type: CottageLocation: Key West
Charming cottage comes complete with a kitchenette packed with all the necessities for a great Key West vacation. Nothing's been overlooked, from the 3 burner stove, refrigerator, coffee-maker, toaster, blender, microwave, flat screen TV, wireless......

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  • Pet Friendly
  • Non Smoking

3 br Key West Condo Vacation Rental

Max Guests: 10Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$5750 - $7550 per month *
Four Bedroom Private Home

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
'CASA ROYAL' allows you to live like a local. Completely renovated using quality finishings, this private single family home consists of two bedrooms, two baths in the main house plus a two bedroom guest cottage with outdoor shower. The master suit......

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  • Non Smoking

$240 - $457 per night *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
ARTIST HOUSE - Welcome to the Artist House, a 2 bedroom 2.5 bathroom rooftop townhome located within the gated community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located so that you can park your car in the private lot and walk to everything Key West has to offer Key West restaurants spec...

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$5000 - $10875 per week *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private home. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community this masterpiece has it’s own private heated pool. Uniquel personal touches, beautiful furnishings and art work can be found throughout the property to...

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$300 - $350 per night *
Pelican Landing Eleuthera Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$188 - $258 per night *
Key West, 'Bella Vita', Luxurious, Sleeps 2-4, Steps from Duval Street

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
The 'Bella Vita' is steps from Duval Street! It is a totally renovated condo. Everything is brand new from floor to ceilings! New cherry wood laminate floors throughout, granite kitchen, new a/c mitshibishi units, new bathroom with european si......

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  • Pet Friendly
  • Non Smoking

$5000 - $8000 per month *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly restored eyebrow 3 bedroom house and is listed on the Key West's Historic House Registry. The house has...

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  • Pet Friendly

Located on Key West golf course, newly decorated & modern, fully furni

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: TownhouseLocation: Key West
3 Bedrooms/2 Bath also roll away couch so sleeps 8 comfortably. Large Deck with Screened in porch. BBQ Grill, Washer/Dryer, Stove/Microwave/Refrigerator, 48-in Flat Screen in HD Direct TV, Wireless Internet. Beautiful view of Hole #1 on KW Golf Co......

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  • Non Smoking

$250 - $471 per night *
Southern Wind

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
SOUTHERN WIND -- A renovated two bedroom two bath two story home located in the Windward Park compound in the heart of Old Town and walking distance to the sites and attractions of the historic district. Southern Wind welcomes you with a large p......

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  • Non Smoking

$470 - $790 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich...neighboring the historic Gato Cigar factory which is now restored and used as county offices. Duval Square is directly across the street with three restaurants,...

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$320 per night *
Lovely, private, Conch home in lush tropical garden setting

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
Lovely, private, conch home in a lush, tropical garden setting located less than 10 min. walk to Smathers ocean beach. Here you can kayak, volleyball, para-sail, jog or roller blade along the beach. Perfect for two couples. The pool is non-gated a......

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  • Non Smoking

Key West Home Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
Coconut Mallory Resort and Marina by Kees Vacations Premium studio condo Bedding Configuration: Unit bedding varies. Unit sleeps 2. Unit Description: This newly refurbished studio, decorated with island-inspired elegance, features a kitchenette with microwave, refrigerator, coffee pot and dishes for four. Relax on the private balcony or patio, or inside watching the flat panel TV and DVD player. O...

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  • Non Smoking

Villa Soleil-Enjoy America's Caribbean with Style and Comfort

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Villa Soleil is an elegant townhouse located in the Truman Annex section of Old Town, close to the ocean and great sunset views. Walk to all of the varied attractions that Key West has to offer, restaurants, nightlife, shopping, theater, gallerie......

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  • Pet Friendly
  • Non Smoking

$458 - $758 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels. Each has it's own private garden with heat optional swimming pool. The open living /dining area fe...

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Best Deal in Truman Annex - Cead Mile Failte

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our home across the pond. We know you will enjoy you......

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  • Non Smoking

$458 - $758 per night *
Townhomes on Windsor #2

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beau......

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  • Non Smoking

Designer Dream 2BR/2BA with Heated Pool and Concierge

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Charming house in Old town near the cemetery and 3 blocks from Duval. Just one 1 block from Seven Fish! Complete renovation in 2006 with Central Air, full designer kitchen and heated pool. 2 Bedrooms (Queen Beds) and 2 Full Baths. House also come......

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  • Non Smoking

$150 - $306 per night *
Coral Caribe

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
CORAL CARIBE: Located in the Coral Hammock community, this lovely 2 bedroom 2.5 bath townhome with sleeper sofa is in the perfect spot, directly in front of the shared pool where you can spend your days sunning and swimming to your heart's cont......

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  • Non Smoking

High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Re

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
(Monthly Rentals Only) : 621 Canfield Lane, Key West, Florida Tucked away at the end of a quiet and peaceful Old Town Lane is this luxurious single family home. Fully renovated and restored in 2007, including designer kitchen and baths. High ce......

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  • Pet Friendly
  • Non Smoking

$1600 - $3408 per week *
Island Spice

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
ISLAND SPICE -- A lovely 2 bedroom, 2.5 bath townhome, located in the historic Foundry building of the prestigious Truman Annex community. The brick exterior, and the brick interior wall of the living room provide you with an Old Town cozy feel, y......

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  • Non Smoking

$200 - $300 per night *
Pelican Landing Aruba Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$3200 - $4000 per month *
2br - South St. Cottage

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
This bright and sunny pool home is situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights, light tile floors and loads of French doors leading from the living room & both the bedrooms to the pool area create a rea...

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  • Non Smoking

$170 - $260 per night *
Casa Atlantica One Bedroom

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled with a mixture of custom made furnishings and unusual objects from all parts of the globe, this ......

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  • Non Smoking

$5500 - $13000 per month *
'BELLA PETRONIA @ THE MEADOWS: 3BR/3.5BA Private Home With Pool & Jacu

Max Guests: 8Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
The Meadows is one of the nicest neighborhoods in the Old Town area, but this exquisitely detailed home on Petronia Street truly stands out. As you turn onto this quiet little one-way lane, you will immediately see this stately new home with its t......

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  • Pet Friendly
  • Non Smoking

$2000 - $5075 per week *
Key West Casa

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
KEY WEST CASA – Beautiful and spacious Shipyard condominium. Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous......

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  • Non Smoking

$1500 - $2900 per week *
A Place in Paradise

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in prestigous Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation......

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  • Non Smoking

$10000 - $27000 per month *
'PORTSIDE MANSION @ THE SEAPORT': 6BR 6.5BA Compound @ Historic Seapor

Max Guests: 12Bedrooms: 6Bathrooms: 2Type: HomeLocation: Key West
In the heart of Old Town, just a half block from the Historic Seaport Harbor, is a very exclusive and unique residence: Two homes and a guest house set on an over-sized corner lot surrounding a spacious courtyard and pool; ideal for a large group ......

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  • Pet Friendly
  • Non Smoking

$150 - $200 per night *
Pelican Landing Dominica Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$5500 - $12000 per month *
HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: VillaLocation: Key West
On a quiet lane just 3 blocks from Smathers Beach is a very special home we’ve named “Hidden Treasure' because it is literally hidden behind a sheltered front entrance with a five foot high louvered fence. Once you've opened the entry door, you'll......

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  • Pet Friendly
  • Non Smoking

2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely remodeled with hardwood floors. Some of the amenities include an outside brick patio with outside seating and ...

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  • Non Smoking

$270 - $480 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features a largee oceanfront balcony accessed from both the living/dining area and master bedroom. The unit features central heat/air, WIFI, cable TV, washer/dryer, well equipped kitchen, 2 baths, security entry, one resereved parking space in the cover garage are...

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  • Non Smoking

STILL A FEW FEB WEEKS,,,CK TODAY !!!!

Max Guests: 6Bedrooms: 2Bathrooms: 1.5Type: TownhouseLocation: Key West
This end unit townhome features 2 bedroom, 1 and ½ bath and is located on President's walk in the prettiest section of the Truman Annex in Key West. The home is decorated in exceptional taste; including a King size bed in the master bedroom with a......

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  • Non Smoking

$2610 - $4200 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed residence, custom finished with classic sophistication and appointed with every modern convenience. Walk a few blocks to fabulous dining and shopping opport...

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$270 - $480 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful tropical flare. It features a huge oceanfront balcony accessed from both the living/dining area and master bedroom with very nice furnishings. It feature central heat/air, cable TV, washer/dryer, well- equipped kitchen, security entry and elevator ac...

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  • Non Smoking

$5500 - $13000 per month *
'BRISAS TROPICALES @ THE MEADOWS': Luxurious 3BR/3.5BA Home + Pool & J

Max Guests: 8Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
THE LIVING AREA: Inside, you'll see that “Brisas Tropicales” has been painstakingly designed for modern tropical living. As you walk in the front door, the very high ceilings give an immediate impression of airiness and light. The living room has ......

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  • Pet Friendly
  • Non Smoking

$1100 - $2320 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a large brick patio and grill. Master bedroom with queen bed and guest bedroom with 2 twins sit on either side of the full bathroom. Well-equipped kitchen for pr...

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Absolutely Paradise

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Located in Old Town Key West tucked off of Simonton Street lies a beautiful home that will entice, entertain, and excite the pickiest of travelers. This spacious three story, 3 bedroom, 2.5 bath home has a private heated pool and lovely deck area ......

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  • Non Smoking

$450 - $720 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Tucked behind a privacy gate, this garden setting L-shaped home is a perfect escape in the heart of Old Town. Louisa's Private Courtyard centers around the contemporary designed pool and patio space to relax and enjoy Key West's year round weather. French doors from the patio enter into the combination living room and kitchen area. Skylights continue to bring the outdoors into the living space whi...

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$2610 - $4200 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed residence, custom finished with classic sophistication and appointed with every modern convenience. Walk a few blocks to fabulous dining and shopping opport...

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$200 - $300 per night *
Pelican Landing Bermuda Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$6600 - $15000 per month *
'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home +

Max Guests: 8Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
If you want to experience Key West at its historic best, Casa Feliz is the perfect choice for your stay. A wide porch graces the front of the house and the grounds have been lushly landscaped in the unique Key West tropical style, including a rare......

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  • Non Smoking

$375 - $650 per night *
3 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
SURF SIDE - Search no further! This fabulous condominium is directly on the Atlantic Ocean. Located at the end of the building closest to the beach, the balcony wraps around giving you access from all of the bedrooms and the living room. Quite simply, the view is stunning! Surf Side has been totally renovated and redecorated in cool, minimalist, modern serenity. The kitchen is fully equipped with ...

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$3500 - $4000 per week *
Heron Estate--Luxury Rental on water with dock. Book now for May 2012!

Max Guests: 9Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
A large four bedroom / 4 bath estate with dock is located on Key West’s only canal, making this the perfect home for boaters and kayakers. The main house, tiled throughout, is comprised of 3 King bedrooms, 3 baths, large open floor plan with livi......

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  • Non Smoking

$2900 - $4400 per week *
Ocean Retreat

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: TownhouseLocation: Key West
Private Home One of the nicest rentals in Key West. Close to Ocean and beach. Access to large private association pool. Three blocks to Duval Street....

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  • Non Smoking

$1750 - $2750 per week *
Truman Annex: Southern Palm Self Catering Spacious town home with larg

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Southern Palm is a townhome located within the gated community of Truman Annex in Key West's Old Town area. The Master Bedroom has Queen Bed, in-suite full bath with Shower and a private balcony. The Guest Bedroom has two single beds that can be ......

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  • Non Smoking

$450 - $873 per night *
Bahama Dreaming

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
BAHAMA DREAMING: A beautifully renovated Conch house conveniently located in the center of Old Town, one block behind celebrated Duval Street, this cottage in Key West is quiet and private. Only a short walk to the many attractions, Key West acti......

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  • Non Smoking

$2900 - $5250 per week *
Large private home just 2 blocks to Duval St

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Step into the luxury Key West lifestyle by staying in this magnificent home. Conch Heaven is conveniently located just 2 blocks from Duval Street, and 4 blocks to the Sunset Celebration. This home is decorated in high quality furnishings, and host......

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  • Non Smoking

$270 - $480 per night *
Beach Club #303

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful tropical flare. It features a huge oceanfront balcony accessed from both the living/dining area ......

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  • Non Smoking

Ocean Breeze Suites-3 Bd, 3 Bath Sleeps 10

Max Guests: 10Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
The Galleon Resort in Key West is a Perfect Resort for You, Your Guests and Your Family. The unit is spacious and very beautiful. The decor is everything you would desire in a Key West accommodation: tropical, clean lines and filled with every nee......

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  • Non Smoking

$2500 - $3600 per week *
'COCONUT PALMS @ THE ANNEX': 2BR/2.5BA Villa on Porter Court facing th

Max Guests: 8Bedrooms: 2Bathrooms: 2.5Type: VillaLocation: Key West
'Coconut Palms' is part of the elegant Porter Court Development and is located in the Truman Annex, Key West's most exclusive gated community. This spacious 2 bedroom Villa has everything you'd want in a Key West vacation home: close to the pool, ......

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  • Pet Friendly
  • Non Smoking

$2800 - $4400 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed residence, custom finished with classic sophistication and appointed with every modern convenience. Walk a few blocks to fabulous dining and shopping opport...

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Petronia Palms for Budget Minded by Duval St Has a Large Pool!

Max Guests: 2Bedrooms: Bathrooms: 1Type: CottageLocation: Key West
Welcome to the 'Sago Palm Cottage'! Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple Properties in Key West. This is for the Budget minded folks looking to be in the heart of Key West and Duval Street, but at a fracti......

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  • Pet Friendly
  • Non Smoking

$160 - $280 per night *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1.5Type: CondoLocation: Key West
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Town Hall, around the corner from Duval Street and offering 'walk to everything' convenience. This bright and airy cottage has tile floors thoughout, king sized bed, one and a half bathrooms, a shared free form pool an...

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$400 - $450 per night *
Pelican Landing St. Kitts Retreat

Max Guests: 10Bedrooms: 3Bathrooms: 4Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$150 - $275 per night *
Coral Garden

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fres......

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  • Non Smoking

$1800 - $2400 per week *
“VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Anne

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: VillaLocation: Key West
This beautiful townhome is to be found in the Truman Annex, Key West’s most exclusive gated community. You’ll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you’ll benefit from the pea......

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  • Pet Friendly
  • Non Smoking

$450 - $720 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport is just steps away with many restaurants, boating activities, historic sights & shops to keep you busy all day! Behind the front fence of the property you can park your car and leave the world behind as you step through the tropical foliage to enter the home from the...

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$2610 - $4200 per month *
Suite Caroline - Mandarin

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed res......

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  • Non Smoking

$380 - $700 per night *
Coconut Cabana

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly res......

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  • Non Smoking

$359 per night *
Ocean Suite at the Galleon Resort

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature's Sunrises, have the convenience of a fully equipped k......

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  • Non Smoking

$7600 - $11000 per month *
Casa Amor - 3BR Residence 2 Blocks from Duval Street

Max Guests: 8Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
Welcome to Casa Amor, our love nest for ten years has been converted into a vacation rental for you. We are located just two blocks from upper Duval Street…home to a multitude of restaurants, art galleries, boutiques, piano bars and historic resid......

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  • Handicap Accessible
  • Non Smoking

$200 - $450 per night *
2br - Luxury Key West Condo -2/2 1/2 ALL NEW!

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
"TEE BY THE SEA" vacation rental (we include 6 bikes free for our guests!!!) If you love...GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT...than you'll love "Tee by the Sea". We're less then 1/2 mile outside of Key West, located in Stock Island. Our condo is in a new gated community with only 52 units that boasts a beautiful heated pool, lush landscaped grounds, fitness ...

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  • Non Smoking

$458 - $758 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels. Each has it's own private garden with heat optional swimming pool. The open living /dining area fe...

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$1200 per week *
Charming Conch Retreat in Beautiful Truman Annex Shipyard

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
The Conch Retreat Condo is in the beautiful gated community of Truman Annex. It's within walking to Duval Street and all main attractions, the best beach on the island, Fort Zachary Beach Park. There is off street parking. It has 2 bedrooms, one w......

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  • Non Smoking

Truman Annex - Renovated End Unit Open floorplan- 1BR/1BA with Great R

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Brand new kitchen appliances, freshly painted, and hardwoods polished March 2010!!! Please read the reviews, we pride ourselves on the wonderful experience our guests have. This one bedroom, fully furnished condo is located in the Truman Annex......

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  • Non Smoking

$2500 - $4500 per month *
Modern home with great location - room for whole family - including pe

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
Updated home with walled in backyard. House with 3 bedrooms & 1 full bathroom & 1/2 bath. Eat- in kitchen has new Whirlpool appliances, tile floors & new cabinets. Family room has tile floors, flat screen TV & new furniture. Two bedrooms are ......

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  • Pet Friendly
  • Non Smoking

$5600 per week *
Casa Colonial Island Luxury in Key West

Max Guests: 7Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Amazing! Hous of Light, Casa Colonial is Key West Luxury at its best! Nestled in a quite residential neighborhood, this amazing three story colonial house is a designers dream home. Walk up the steps to an enchanting veranda with comfortable seati......

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  • Non Smoking

$225 - $275 per night *
Ray's Retreat

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine......

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  • Non Smoking

$290 - $460 per night *
Catherine House

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, or shopping on Duval Street. Better yet, it is just three blocks to a beach (Duval & South Streets). This house can comfortably sleep f......

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  • Non Smoking

$5000 - $10500 per month *
'CASA DE ROSALIE @ BAYVIEW PARK': Freshly Renovated 3BR/2BA Home In To

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
'Casa de Rosalie' is a classic conch home located right across the street from Bayview Park, with its tennis courts and community activities. This stately home has many of the original features from when it was built in 1889, including the origina......

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  • Pet Friendly
  • Non Smoking

$2500 - $3500 per week *
“WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthou

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
Directly facing the Gulf of Mexico right next to Mallory Square, this beautiful penthouse condo is the perfect place to spend your stay in Key West. With panoramic views of the water and cruise ships as they dock nearby, you’ll be tempted to just ......

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  • Non Smoking

$110 - $290 per night *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
OSPREY - This bright and colorful studio cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West. This is absolutely the ideal location just three blocks from famous Duval Street with its incredible art galleries, boutiques, museums, attractions, restaurants, and nightclubs.  ...

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$320 - $395 per night *
New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval

Max Guests: 5Bedrooms: 2Bathrooms: Type: HomeLocation: Key West
Key West Potter's Cottage. New owners for 2011. The property has been updated with new furniture, new beds, painted and decorated. The upstairs has a master suite with a king sized bed, sitting / office area and a brand new bathroom. ......

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  • Pet Friendly
  • Non Smoking

$1250 - $1750 per week *
Eaton Manor

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Eaton Manor sits on the north side of LaBrisa and provides easy access to Smathers beach, where you can sail, boat, kiteboard, parasail, walk, run, roller blade and witness the most beautiful morning sunrise. Though Eaton Manor is only seconds aw......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 3Type: CondoLocation: Key West
Luxury three level town home in a gated community. The home features 2 master suites, 3 full baths, large rooms, vaulted ceilings, two car garage, private rear yard, elevator and hurricane/wind resistant doors and windows. Upgraded finishes include tile floors, granite countertops in the kitchen and baths, stainless steel appliances and security system. Bedding Configuration: 2 Queen, 1 Other Addi...

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  • Non Smoking

2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Bright, tropical colors and tile floors provide an island ambience to this two bedroom, two bathroom ocean view condominium. The living area and master bedroom both open onto the private balcony and create a relaxing indoor/outdoor place to unwind at the end of your day. Or enjoy the lush grounds with tennis courts and twenty-five by fifty foot heated pool. Bedding Configuration: 1 King, 2 Twin Ad...

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  • Non Smoking

$225 - $435 per night *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2.5 bath townhome located in the gated rooftop community of Duval Square on Duval Street, in the middle of the action. Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval Street in Old Town Key West and a few blocks from the beach; leave the car keys with your luggage -- everyting you want to...

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$258 per night *
2br - Hidden Treasure w/ heated pool 2 blocks from Duval

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CottageLocation: Key West
Hidden Treasure is a 2 bedroom, 2 bathroom vacation cottage with 2 king beds and a queen sleeper sofa. This cottage has high ceilings, which gives it a bright, warm, and welcoming feeling which is just how Key West should feel! It has a full kitchen, living room and dining area. There is a large private deck outback, a heated pool and it is only two blocks from the infamous Duval street!...

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  • Non Smoking

Mojitoville: Pet-Friendly Old Town Cottage W/ Private Pool

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
The historic cottage features two bedrooms, one with king pillow top bed , 27 inch flat screen CATV and the other with queen pillow top bed , 27 inch CATV. The wonderful loft has two twin beds and a private sitting area for relaxing as well as a 2......

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  • Pet Friendly
  • Non Smoking

$1100 - $2320 per week *
2 br Key West Condo Vacation Rental

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this home is in a great location and a great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room offering a view of the neighborhood and BBQ grill. The best priced 2 bedroom 2 bath condo in Truman Annex with a queen bed with bathroom ensuite and guest ...

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$6000 - $15000 per month *
'SOUTHERN STAR' @ WILLIAM STREET' Historic 3BR/3BA Home with Pool...

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
The Living Area: In the living area, you'll see that while this home has been preserved, it has also been updated for modern living. The living room has large windows and three sets of French doors, and there's a 50' high definition TV with home......

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  • Non Smoking

$3500 - $6500 per month *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL ANGELA COTTAGE This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings & many windows create a relaxing Key West cottage vacation. A spiral staircase from the living area leads to an open loft o...

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  • Pet Friendly

$9000 - $16000 per month *
'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Larg

Max Guests: 10Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
'Casa Blanca 1888' has everything you would want for your stay in Old Town Key West. Its central location in historic Old Town at White Street and Truman Avenue means you will be just steps from the White Street art gallery district, restaurants, ......

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  • Pet Friendly
  • Non Smoking

$4500 - $11000 per month *
'COLORFUL CONCH @ THE SANCTUARY': Immaculate 4BR/3BA Private Home, Poo

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
This beautiful private home has everything you could want in a vacation home. It has been meticulously furnished and maintained inside and out, and is located in 'The Sanctuary', a lush enclave set within the private gated community of the Key Wes......

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  • Pet Friendly
  • Non Smoking

2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Located in Old Town, this home is conveniently located within walking distance to the Seaport, restaurants, and major attractions. The house has 2 bedroom 2 bath and a nice backyard with a pool. Bedding Configuration: 2 Queen, 1 Other Additional Features: * Entertainment: Cable TV, DVD Player, internet, Ipod player * Geographic: Downtown, Near Beach * Kitchen: Full Kitchen, Microwave * Living: Cen...

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  • Non Smoking

Anderson's Key West Home

Max Guests: 10Bedrooms: 4Bathrooms: 3.5Type: HomeLocation: Key West
Beautiful vacation home in Key West Truman annex. Conveniently located two and a half blocks from Duval Street and Mallory Square. Fully furnished, three story, four bedroom, three and a half bath. The master bedroom has a king bed with a privat......

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  • Pet Friendly
  • Non Smoking

$380 - $730 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavillion with an ornate iron & glass heron detail. A unique piece of Key West. Each of the bedrooms open...

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  • Pet Friendly

$3500 - $4000 per month *
'SUNSET DREAMS 2 @ FLORIDA BAY': Luxurious 2BR/2BA Waterfront Condo...

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
'Sunset Dreams 2' has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world with a large balcony overlooking Florida Bay and t......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$1200 - $2100 per week *
Shipyard 253

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2 twins and 1 pullout sofa. There is a balcony on the front and the back of the unit. The back balcony has a BBQ. The unit comes with one assigned parking spot. This home is care......

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  • Non Smoking

$3000 - $5000 per month *
2 br Key West Beach Front Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighbo...

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$299 per night *
Casa De Vino - 3 bedroom town home with resort pool

Max Guests: 8Bedrooms: 3Bathrooms: 3Type: TownhouseLocation: Key West
Fine yet affordable accommodation located in the gated community of Coral Hammock known for its well manicured lush tropical landscape & resort pool. Located poolside with fabulous views from bedrooms, living room & back porches great for entertai......

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  • Non Smoking

$1600 - $2000 per week *
Condo at Oceanside Marina, Stock Island, Key West

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Imagine waking up every morning to the sun rising over the Atlantic Ocean. That's what you will experience with this beautifully furnished three bedroom condo right on the ocean at Oceanside Marina. With direct views of the ocean from the living r......

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  • Handicap Accessible
  • Non Smoking

$1100 - $1900 per week *
Charming, downtown, walking distance to all activities, quiet, gated c

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Crocodile Ranch is a 2 bedroom 1 bath, lower level, renovated 'Shipyard' home located in the Truman Annex. This is a perfect location for families or friends. Master bedroom has a queen bed and the second bedroom has two twin beds. The kitchen is ......

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  • Non Smoking

$1200 - $1750 per week *
Shipyard 106-2

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony with a lovely view of the Key West Harbor from the spacious 2nd floor deck. In case you would like to wo......

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  • Non Smoking

$1300 - $2864 per week *
Bahamian Reed

Max Guests: 5Bedrooms: 2Bathrooms: 1.5Type: CondoLocation: Key West
BAHAMIAN REED: A bright and colorful 2 bedroom 1.5 bathroom townhome located in the prestigious community of Truman Annex all within the Old Town district of Key West. A great location and beautifully furnished accomodation make this property th......

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  • Non Smoking

$150 - $200 per night *
Charming Yacht Located in Exclusive, Beautiful Key West Harbour Yacht

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: YachtLocation: Key West
Come stay aboard BOW'D UP, a classic 42ft Hatteras Sportfish! BOW'D UP is docked at Key West's most luxurious marina, Key West Harbour Yacht Club. The serene peaceful location is the perfect place to escape, but is still within a short distance t......

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  • Non Smoking

Tropical Retreat Near Duval Street!

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Authentic slice of Old Key West near Bahamas Village coupled with the modern amenities of new construction, this is our ''escape-from-RI-winters'' private retreat that we would like to share with you. Our home was designed with entertaining in m......

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  • Non Smoking

$4750 - $7800 per month *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL This amazing restoration of a majestic Key West bungalow is incredible. Modernists will love this property. This two bedroom, two bath home has just been completely renovated. The clean lines of the Brazilian cherry floors to the contemporary furnishings, this is a high end home. The kitchen has top of the line built-in appliances. The master suite with queen bed sits to the ...

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$1300 - $2610 per week *
2 br Key West Condo Vacation Rental

Max Guests: 5Bedrooms: 2Bathrooms: 1.5Type: CondoLocation: Key West
BAHAMIAN REED: A bright and colorful 2 bedroom 1.5 bathroom townhome located in the prestigious community of Truman Annex all within the Old Town district of Key West. A great location and beautifully furnished accomodation make this property the home away from home you have been seeking. The property is conveniently located just a hop, skip and a jump from all the reasons you came to Key West: Fo...

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$1470 per week *
Beautiful Waterfront Single Family Home - 5 miles from Key West

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
This is a beautiful Spanish style home on a clean swimming canal 9 miles from Duval Street, Key West. Our home is just 4 houses from the end of the canal and the backwaters of the Gulf. Many uninhabited islands are nearby for exploring and discove......

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  • Non Smoking

$458 - $758 per night *
Townhomes on Windsor #4

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beau......

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  • Non Smoking

Rose Lane Villa's Villa Porta 1 bedroom, 1/2 block off Duval

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: VillaLocation: Key West
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa......

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  • Non Smoking

$160 - $313 per night *
Big wonderful apartment in central Nice, by the beach

Max Guests: 6Bedrooms: 2Bathrooms: Type: ApartmentLocation: Key West
The apartment is 90 square meters. It has light and spacious rooms with a minimalistic but functional furnishing. The apartment has room for 6 persons. (1 double bed, 2 single beds and 1 double bed settee.) The apartment has the following facili......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$1100 - $2320 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
SIESTA BAY -- Beautiful two bedroom one bath upstairs condo in Truman Annex, just steps away from the shared pool and within walking distance of anything you'd want to do in Key West. Bright, airy and with plenty of Key West charm Siesta Bay will provide you with all the comforts you are looking for in a home away from home. This property is the perfect combination of quiet retreat and the best lo...

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$120 - $300 per night *
Osprey

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
OSPREY - This bright and colorful studio cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West. This is absolutely the ......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$249 per night *
2br - KEY WEST WATERFRONT HOME AND YACHT

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
Ahoy! PirateHead Cove, your affordable vacation dream-come-true is fully booked. ****NOTE: If you send an incomplete form, (no phone number, number of adults and children wanting to rent, etc), we cannot respond to your inquiry for availability.* Choose from two options, beautiful waterfront home with all the comforts(and more!) or a romantic and unique alternative, a 40' Hatteras Yacht Floatel wh...

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  • Non Smoking

$4900 - $5900 per week *
Ocean Paradise

Max Guests: 8Bedrooms: 3Bathrooms: 4Type: HomeLocation: Key West
This is a One Week Minimum Stay!!! Three bedroom four bath private home. Heated Pool with massage water jets and special colored lighting. Breathtaking sunsets from third floor deck overlooking the Ocean. High Def Plasma TV. Surround stereo throu......

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  • Pet Friendly
  • Non Smoking

$2600 - $3800 per week *
CHILMARK SOUTH - paradise found in truman annex!

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
From the minute you walk through the front door, you'll feel like you're in paradise. The view is spectacular day and night. Located 2 blocks from Duval Street where all the action happens, this waterfront condo at Harbour Place in the private gat......

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  • Handicap Accessible
  • Non Smoking

$1100 - $2000 per week *
Old Town location close to beach, shops & more

Max Guests: 5Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
The Fort Zach condo has two bedrooms, one with a queen size bed and the second with two twin beds. The one bathroom has a tub with shower. Enjoy your morning coffee on the back porch overlooking the pool. Later you can sear some Key West shrimp o......

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  • Non Smoking

$450 - $720 per night *
Louisa's Private Courtyard

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Tucked behind a privacy gate, this garden setting L-shaped home is a perfect escape in the heart of Old Town. Louisa's Private Courtyard centers around the contemporary designed pool and patio space to relax and enjoy Key West's year round weather......

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  • Non Smoking

$1100 per week *
Island Escape Condo in Beautiful Truman Annex

Max Guests: 3Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
This lovely Island Escape Condo is located in the beautiful gated community of Truman Annex Shipyard. Location is everything. It's 2 blks to Duval Street, Fort Zachary Beach, the best beach on the island. Mallory Square is walking distance where s......

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  • Non Smoking

Gated Private Luxurious Getaway-Truman Annex (Private Pool)

Max Guests: 7Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block from Duval and Mallory Square. Completely private swimming pool with covered porches upstairs and down. Beautiful tile floors......

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  • Non Smoking

$1200 per night *
Canal Front, Boat lift, Sunny and Large, Master Suite, HDTV, Fully Fur

Max Guests: 12Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Welcome to the tropical island of Key West, Florida, the perfect destination for travelers looking for relaxation and comfort, or travelers looking for adventure. Our beautiful single family home is located on a canal just ten miles from downtow......

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  • Pet Friendly
  • Non Smoking

$375 - $662 per night *
Surf Side

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
SURF SIDE - Search no further! This fabulous condominium is directly on the Atlantic Ocean. Located at the end of the building closest to the beach, the balcony wraps around giving you access from all of the bedrooms and the living room. Quite sim......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$1300 - $2610 per week *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to restaurants, nightlife, entertainment, shopping and Fort Zachary Taylor State Park beaches. This property is a great base from which to explore our tropical...

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$1680 - $2870 per week *
2br - Duval Square Retreat

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers a well- equipped kitchen, a living room that opens to a patio. Upstairs there is a master bedroom with balcony and en-suite bath and a second bedroom and bath....

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  • Non Smoking

$4500 per week *
Waterfront Views from Dolphin Watch

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than two blocks from Duval Street and beautiful Mallory Square sunsets. You can also see the sunset from your own private balcony! Wa......

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  • Non Smoking

$5000 - $9000 per month *
CARIBBEAN SOUL ~ Clean, Spacious & Central

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: Location: Key West
Quintessential Key West vacation home leaving nothing more to be desired. Framed by a white picket fence you will be welcomed to this classic 2 story with double porches perfect for enjoying the island breeze. Beautifully landscaped with potted ......

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  • Non Smoking

$320 - $500 per night *
Havana Lane

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence o......

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  • Non Smoking

$270 - $480 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful tropical flare. It features a huge oceanfront balcony accessed from both the living/dining area and master bedroom with very nice furnishings. It feature central heat/air, cable TV, washer/dryer, well- equipped kitchen, security entry and elevator ac...

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$300 - $350 per night *
Pelican Landing Bermuda Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$450 - $720 per night *
Casa Margarita

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport is just steps away with many restaurants, boating activities, historic sights & shops to keep you busy all day! ......

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  • Non Smoking

$370 - $620 per night *
Whitehead House

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most photographed "Prohibition fence" in Key West, this home has a large private, sunny pool and deck, off street parking ( ......

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  • Non Smoking

$200 - $370 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighborly and relaxing atmos...

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$4000 - $5500 per month *
1br - Tropical Serenity

Max Guests: 2Bedrooms: 1Bathrooms: 1.5Type: HomeLocation: Key West
30 DAY MINIMUM. An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been completely restored to a pristine condition. A large front yard with quaint front porch give this cottage the curb appeal of your dreams. Step in to the comfortable living room with Brazilian cherry floors and a white cotton sofa to relax on. A...

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  • Non Smoking

$200 - $300 per night *
Pelican landing Eleuthera Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1890 - $3220 per week *
2br - Catherine House

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, or shopping on Duval Street. Better yet, it is just three blocks to a beach (Duval & South Streets). This house can comfortably sleep four and offers a fully equipped kitchen, two bedrooms, living area with outside dining, BBQ and a small pool. The open style living and dining area has a c...

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  • Non Smoking

$200 - $370 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighborly and relaxing atmos...

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$300 - $463 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condominium for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. Located on the Atlantic Ocean with views of the sparkling blue-green waters from the living room, second bedroom and master bedroom. The master...

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$825 - $1668 per night *
The Victoria House

Max Guests: 12Bedrooms: 5Bathrooms: 5.5Type: HomeLocation: Key West
THE VICTORIA HOUSE (Formerly Treetop Villa) - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart ......

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  • Non Smoking

$3500 - $4500 per month *
Campbell Courtyard Townhouse 'In the Sky'

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Few properties in Key West can offer a true combination of quality, location and privacy like this one! Perched above the 600-block of Fleming Street (between Simonton and Elizabeth), this 2-story, 1, 000 sq. ft. townhouse 'in the sky' offers 2 be......

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  • Non Smoking

$3000 - $3733 per month *
The Loft at Echo Gardens

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is located one block from the world famous Duval Street. This stunning second floor, one bedroom one bath condominium is fil......

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  • Non Smoking

$458 - $758 per night *
Townhomes on Windsor #3

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beau......

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  • Non Smoking

$13500 per month *
A Modern Luxury Home with Style and Grace.

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
A place to sequester yourself in nature & design. The style is tribal meets 20th century modern, where Iranian Gabbeh rugs, Italian furniture, Haitian art & abstract paintings co-exist perfectly. But most distinct is the overlap of indoor & outdoo......

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  • Non Smoking

$1200 - $1850 per week *
Pristine Condo with Pool & Ocean Peek, 2 Bikes in Key West's Truman An

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
This condo overlooks Truman Annex's lush landscaping & Shipyard pool. A short walk or bike ride to one of the best beaches on the island. You are moments from Mallory Square where sunset is celebrated every day with world class street theater. The......

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  • Non Smoking

$9000 - $16000 per week *
'CONCH CASA GRANDE @ TRUMAN ANNEX': Grand 7BR/7BA Home, 6 Master Suite

Max Guests: 12Bedrooms: 7Bathrooms: 7Type: HomeLocation: Key West
Conch Casa Grande might well be the largest home available for vacation rental in the Truman Annex, which is appealing to anyone who wants to have some elbow room during their stay in American Paradise. But what really sets this home apart is its ......

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  • Pet Friendly
  • Non Smoking

$120 - $135 per night *
Peaceful 2 BR Condo with All Amenities

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Enjoy the comforts of home in the midst of paradise. Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet ......

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  • Pet Friendly
  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$150 - $200 per night *
Pelican Landing Andros Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$130 - $165 per night *
Charming Caretaker's Apartment in Old Town

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: Location: Key West
This caretaker's apartment is in Old Town Key West, removed from the noise but close to all the attractions. Four blocks from Duval, two blocks from Truman; six blocks from the Atlantic Ocean and beaches. Bike or walk to all that Key West has to o......

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  • Non Smoking

$2500 - $3500 per week *
Truman Annex: The Plantation SELF CATERING beautifully landscaped rea

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: TownhouseLocation: Key West
'The Plantation' is a 3 bed 3 bath townhome located within the gated community of Truman Annex in Key West's Old Town area. In addition to the Master Bedroom, with its King Bed and private balcony, and the Guest Bedroom with two single beds, which......

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  • Non Smoking

$340 - $682 per night *
2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic district of old Key West, an ideal location for walking and biking to all the attractions, yet quiet...

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  • Pet Friendly

Tom's Lanai: 1800 Atlantic, Amazing View. Heated Pool!

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Since this has just been launched please check the reviews on my other condo. You will find the link for that in addition to my website half way down this page. Located only two minutes from the airport and five minutes from downtown the area ......

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  • Non Smoking

$4000 per month *
You've Arrived at your Perfect Island Get Away With Private Pool

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Enter The Gate To Your Private Pool And Garden. Covered Porch Looks Poolside. Ideal Cottage Setting With Waterfall To Ease Away The Stress Of The Real World. This 2bed/2ba Cottage Is Just 6 Blocks From All The Fun Of Duval St In Old Town Key Wes......

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  • Pet Friendly
  • Non Smoking

$3300 - $5500 per month *
'SUNSET DREAMS @ FLORIDA BAY': Luxury 3BR/2BA Waterfront Condo by Mari

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: CondoLocation: Key West
'Sunset Dreams' has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world with a large balcony overlooking Florida Bay and the......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$220 - $369 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
FLORIDA PALM: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and sunshine at your whim. Full equipped kitchen allows for great family meals cooked at home. Key West vacation rentals Condo offers street view; complex offers oc...

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$4950 - $6875 per month *
4 BR Private Oasys With Heated Pool Close to Beaches

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
This 4 bedroom, 2 bath ranch style single family home is located 3 blocks from Smather's Beach and 5 blocks from Higgs Beach on the Atlantic side of Key West. The walled property is surrounded by lush, tropical landscaping and there is a private h......

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  • Pet Friendly
  • Non Smoking

$975 - $1595 per week *
Villa Jade Marie Stunning 5* Luxury Villa with 10x5m Private Pool & Ho

Max Guests: 8Bedrooms: 4Bathrooms: 3.5Type: VillaLocation: Key West
Villa Jade Marie is a magnificent 5* luxurious villa situated on one of the prime plots of this new development in Playa Blanca. Approx 10 minutes walk to the nearest beach/bars and restaurants, and the local supermarket is only 2 mins walk away. ......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$250 - $450 per night *
Oceanfront Condominium - Direct Oceanfront at the Coral Reef

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
You feel it the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to disco......

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  • Handicap Accessible
  • Non Smoking

$4000 - $6000 per month *
'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool..

Max Guests: 8Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
'Natalie's Bahama Conch' is located in the Sanctuary at the Key West Golf Club. Just about everything in the house has been redone, from top of the line appliances int he kitchen to the Tommy Bahama designer furnishings throughout. In short, no ex......

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  • Pet Friendly
  • Non Smoking

$625 - $1378 per night *
3 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
DUVAL PENTHOUSE -- A large luxury apartment located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist, comfortable island style furnishings and artwork suited to the casual lifestyle here in Key West. Fabulous terraces abound, g...

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$870 - $2000 per night *
Dreaming On Duval

Max Guests: 10Bedrooms: 5Bathrooms: 4Type: HomeLocation: Key West
There's a new place on Duval Street in historic Key West and it is unique! Dreaming On Duval premieres in early 2010 as the most luxurious single family vacation rental on Duval Street. Steps to everything Key West has to offer, this private hom......

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  • Non Smoking

$410 - $700 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the property through a secure privacy fence into the pool courtyard area. The large house towers above with high ceilings and oversized windows on both the ground floor and second story. The great room has a large sectional sofa providing ample seating as well as a convenient ha...

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  • Pet Friendly

$2500 - $3500 per week *
Shipyard 210 - 4

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
The first floor includes a front porch, bedroom, completely remodeled kitchen, remodeled lower bathroom, large open living area, and beautiful French doors leading to a private deck and backyard. The backyard includes a table for six and new gas g......

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  • Non Smoking

$225 per night *
Beautiful Duval St. Condo, Location, Location!!!!

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Location, Location, Location!!! You can't find a better location than Duval St. One of only three unique units. This Condo is above and behind Antonia's Restaurant (best Italian food in Key West!). The Condo is walking distance to Ft. Zachary ......

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  • Pet Friendly
  • Non Smoking

Historical Conch Home with Pool

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
This conch single family home (listed on the National Historic Register) located in the heart of Key West's “Old Town District” is situated 5 blocks from Duval St. and 1 block from Key West Harbor water front boardwalk, sunset activities, great w......

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  • Non Smoking

Quaint Houseboat with wet bar and awesome views - Key West Fishing Vac

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: Location: Key West
This charming two bedroom, two bath houseboat is permanently docked at beautiful Sunset Marina in Key West. Just minutes from the airport, you can drop your luggage and drop your line as soon as you arrive!...

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  • Non Smoking

Rose Lane Villa's Villa Vista 1 bedroom, 1/2 block off Duval

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: VillaLocation: Key West
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. This one bedroom Vill......

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  • Non Smoking

$200 - $340 per night *
Ann Street Tranquility

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Old City Hall, around the corner from Duval Street and offering '......

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  • Non Smoking

4 br Key West Condo Vacation Rental

Max Guests: 14Bedrooms: 4Bathrooms: 4Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$600 - $1200 per night *
William Skelton -- Location, location, location -- in Old Town Key Wes

Max Guests: 16Bedrooms: 6Bathrooms: 3Type: HomeLocation: Key West
A hidden gem in Old Town!! It can be rented as a 4 bedroom/3 bath or as a 6 bedroom/4 bath. Our flexibility allows you more flexibility! The house is really unique with its exposed Dade County Pine walls, private porches, and a widow’s walk on th......

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  • Non Smoking

$4500 - $5867 per month *
Manatee Manor

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then c......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$458 - $758 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels. Each has it's own private garden with heat optional swimming pool. The open living /dining area fe...

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$4000 - $9425 per week *
3 br Key West Home Vacation Rental

Max Guests: 7Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Admiral's Paradise - Style is supreme in this 3 bedroom 3.5 bath single family home on Admiral's Lane in the exclusive Truman Annex community. Enjoy the abundant french doors that open the entire downstairs to the outdoors and give this home easy open-air living. A superb location, this home is walking distance to all the best Key West has to offer: Duval Street, Fort Zachary Taylor State Park and...

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$825 - $1668 per night *
5 br Key West Home Vacation Rental

Max Guests: 12Bedrooms: 5Bathrooms: 5.5Type: HomeLocation: Key West
THE VICTORIA HOUSE (Formerly Treetop Villa) - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart of Key West’s Old Town, within walking distance of restaurants, shops, galleries, museums, theaters, seaports, Atlantic beaches, Gulf sunsets, watersports...

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  • Non Smoking

$320 - $500 per night *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and style. Centrally located in an Old Town residential neighborhood the cottage is just a few blocks away ...

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  • Pet Friendly

$5500 - $9000 per month *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden area. Nicely decorated throughout, this two bedroom, two and a half bath home has a open. airy kitchen that...

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  • Pet Friendly

$3150 - $5600 per week *
4br - Amelia #039;s Great Escape

Max Guests: 9Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
Welcome to the Beach!!!! No this house isn't oceanfront! But in Key West almost anything is possible. This house has just been transformed into a relaxed beach house with many updates & upgrades. New furniture, cabinets and appliances as well as a redecorating of everything including the garden make this a great vacation show place. Enter the house with gingerbread touches on the exterior to see a...

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  • Non Smoking

$458 - $758 per night *
Townhomes on Windsor #1

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beau......

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  • Non Smoking

$4500 - $5867 per month *
Seaside 33

Max Guests: 4Bedrooms: 2Bathrooms: 3Type: CondoLocation: Key West
Luxury three level town home in a gated community. The home features 2 master suites, 3 full baths, large rooms, vaulted ceilings, two car garage, private rear yard, elevator and hurricane/wind resistant doors and windows. Upgraded finishes includ......

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  • Non Smoking

$300 - $350 per night *
Pelican Landing Bonaire Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$300 - $350 per night *
Pelican Landing Dominica Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1400 per week *
2br - Stay in the nicest part of Truman Annex

Max Guests: 6Bedrooms: 2Bathrooms: 1.5Type: TownhouseLocation: Key West
This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered deck for your morning coffee, or romantic evening. The second bedroom has twin bed's with its own private deck, also...

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  • Non Smoking

$1250 per week *
Galleon Resort Efficiency Historic District

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Location..Location...Location...this one has it all! Resort is located on the Ocean and is within steps of famous Duval Street. The Galleon Reosrt offers many amenities to enhance your vacation needs. The Efficiency Unit features a King Size Bed, ......

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  • Non Smoking

4 br Key West Home Vacation Rental

Max Guests: 10Bedrooms: 4Bathrooms: 3.5Type: HomeLocation: Key West
Art Deco Dream! Key Haven, open water views & canal front home. Totally private on two lots, this unique ground level masterpiece has it all. Extensive balconies surround the home with four Bedrooms and four and one half Bathrooms, pool, glorious water views, double car garage entertainment room, two wet bars, an enormous 1500 sq ft master suite, boat lift & seawall. Truly a one of a kind home. Th...

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  • Non Smoking

$2750 per week *
Luxurious Ocean Front Oasis in Key West

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
No attention detail spared in this fabulous oasis. Perfect for a get-away with friends or family. A touch of Vegas in Key West, black marble floors, cedar lined closets, custom cabinets and mirrors. This property features a 60 ft private wrap arou......

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  • Non Smoking

$340 - $682 per night *
2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
TROPICAL DREAMING -- This tropical 2-bedroom home has been professionally decorated and furnished. There are classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. Many large windows frame the tropical landscape. Located one block from celebrated Duval Street , it is close to world-class restaurants, shops, art galleries and nightclubs. The ...

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  • Pet Friendly

$220 - $430 per night *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch, two bedrooms and two baths. There is a shared pool and sunning area that overlooks the world famous Duval Street. Central air conditioning/heat. Bedd...

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$345 - $531 per night *
Key West Crown Jewel

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
KEY WEST CROWN JEWEL -- We know that you will enjoy staying in our little bit of Paradise. This is a 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space and vaulted ceilings. Enjoy absolutely breathtaking ocean views an......

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  • Non Smoking

$300 - $350 per night *
Pelican Landing Flamingo Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$3500 - $5000 per month *
Florida Keys Tropical Waterfront Home

Max Guests: 8Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Only ten miles from the exciting City of Key West, you will enjoy private tropical relaxation. Lagoon style heated swimming pool with beach entry and waterfall. Outside bathrooms in a cabana for changing and relaxing. Thousands of square feet of p......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$4000 - $7500 per month *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Unique oceanfront living sitting 65 feet from the Atlantic awaits you at the Key West Beach Club. Listen to the water as ocean breezes cool you. This elegant 2 bedroom unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. Unit amenities include central air/heat, cable TV, washer/dryer, well-equipped kitchen, 2 baths, security en...

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$1400 per week *
Attitude Key West : Get that Chillin' Feeling

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Reno's Completed May 2010! This unique unit is OUR VACATION HOME NOT JUST ANOTHER RENTAL. Located in the Ship Yard of Truman Annex a luxury community in the heart of Old Town Key West. It is a 1st floor unit that boasts 2 sets of french doors o......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 3Type: CondoLocation: Key West
Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Bedding Configuration: 1 Queen, 2 Twin, 1 Sleeper Sofa Additional Features: * Convenience: Area FitnessCenter * Entertainment: C...

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  • Non Smoking

$2800 per week *
Deluxe 3 BR Villa at Fort Zach Beach in Historic Old Town Key West Sle

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: VillaLocation: Key West
Please include your phone numbers with your inquiry (required), even if you are overseas... Since there are three completely self contained areas with up to three kitchens and three parking spaces, this villa can accommodate the Single Perso......

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  • Non Smoking

Luxurious, Elegant, quiet

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
One of the most beautiful homes in Key West located on a wide canal with 35' of dock space available! Custom design heated pool. Home has Travertine Marble in Living Room & Kitchen, granite counter tops with cherry cabinetry, stainless steel appli......

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  • Non Smoking

Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool!

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple Properties in Key West Welcome to Petronia Palms! and the 'Queen Palm Cottage'! Ask about AUGUST specials!! The safest location in Key West! Call for last minute July s......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

Palm Court is located in historic Old Town Key West, just two blocks f

Max Guests: 3Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
Our Guest Suite is a one-bedroom suite with queen-size bed and a living room with sleeper sofa . It is furnished with a mixture of antiques, oriental rugs and has original art work. It is outfitted with air conditioning, cable TV, stereo with CD p......

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  • Non Smoking

GECKO GETAWAY ~ Old Town Condo near the Historic Seaport

Max Guests: 5Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
Hidden away yet in the middle of it all! Cute & comfortable 2nd story condo perfect for getting away from the cold northern winters. Open living area with fully equipped kitchen and granite breakfast bar with dining for 4 plus downstairs half bath......

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  • Non Smoking

3 br Key West Condo Vacation Rental

Max Guests: 10Bedrooms: 3Bathrooms: 4Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$225 - $275 per night *
Coral Hammock 39

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Coral Hammock is one of the newest gated communities with 55 luxury resort homes with a lavish Clubhouse, Pool and lushly landscaped grounds. These custom single family homes recall the romantic charm of old Key West with spacious floor plans, vau......

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  • Non Smoking

$150 - $320 per night *
1 br Key West Ocean Front Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighborly and relaxing atmos...

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$1250 per night *
Summer Discounts Truman Annex, Key West

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Flip Flop Retreat on President's Walk is a convenient walk or bike ride to Old Town for entertainment, shopping, restaurants, and outdoor activities. As a Guest in Flip Flop Retreat you have all conveniences you need to relax and entertain in st......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$225 - $471 per night *
At Home Key West

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation r......

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  • Non Smoking

$4000 - $11000 per month *
'TROPICAL JEWEL @ ELIZABETH': 2BR/2BA Restored Conch Cottage @ The Sea

Max Guests: 7Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
If ever a home was a precious jewel, it is this immaculate restoration located on 320 Elizabeth Street just two blocks from the Historic Seaport. When you enter through the front gate, you'll be struck by the privacy of the front yard, and the att......

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  • Pet Friendly
  • Non Smoking

$4400 - $10500 per month *
'THE LILAC COTTAGE @ SOLARES HILL': 2.5BR/2BA Old Town Cottage, Quiet

Max Guests: 7Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
This charming home has just been completely renovated, from its gingerbread on the front porch to the restored Dade County Pine inside. All of the furnishings are brand new and of the highest quality. The location is ideal, just 5 blocks from Duva......

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  • Pet Friendly
  • Non Smoking

1br - One Bedroom Deluxe Suite (Deck Villa)

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
Villas Key West is a small (7 unit) guesthouse located 200 feet from Duval Street! Our accommodations are apartments set in 2 old historic Key West houses joined by a deck and temperature controlled pool. The very heart of Old Town Key West within easy walking distance of everything. There is no better location in Key West…. The 1 BEDROOM DELUXE VILLA was completely gutted and renovated in 2007. N...

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  • Non Smoking

$350 per night *
Location, Location, Location! Ocean View, Lagoon Beach Front

Max Guests: 10Bedrooms: 3Bathrooms: 2Type: Location: Key West
This 83' Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 2. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 1 pull-out couch, all kitchen appliances, washer/dryer, full kitchen & utensils, pots and......

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  • Non Smoking

$225 - $435 per night *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around the area including our super size Sea Turtle painting. You have your own covered parking space, which is gated and secure. ...

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$250 - $471 per night *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
SOUTHERN WIND -- A renovated two bedroom two bath two story home located in the Windward Park compound in the heart of Old Town and walking distance to the sites and attractions of the historic district. Southern Wind welcomes you with a large private shady deck and outdoor dining area. Once inside the traditional architecture gives you an open floor plan with hardwood floors and large windows to ...

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$1700 - $3625 per week *
2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort Zachary Taylor State Park and the nightly festivites in Mallory Square. Artist Garden is a delightful home with an open fl...

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$458 - $758 per night *
Townhomes on Windsor #5

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beau......

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  • Non Smoking

$160 - $240 per night *
Galleon Resort Efficiency in Old Town

Max Guests: 2Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a kitchenette with mini-refrigerator, microwave, coffee maker and dishes. For y......

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  • Non Smoking

$1500 - $2900 per week *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome. Lots of space with for a family of 6. Master bedroom has bath ensuite and private balcony. Living room opens to your private deck for sipping cocktails, grilling the day's catch and reliving the day's activities. Or start your day there with toasted Cuban bread and a ...

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$5200 - $8000 per month *
Brass Palm Villa, Private Luxury Home - ESCAPE TO PARADISE!!

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
Private Luxury Home with Heated Pool surrounded by lush tropical landscaping. Our vacation rental home is a fusion of Florida style living and Caribbean design, creating an ideal contemporary “Floribbean” villa in the Casa Marina district of Key ......

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  • Pet Friendly
  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$200 - $300 per night *
Pelican Landing Harbor Island Suite

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Non Smoking

$190 - $384 per night *
Tranquility

Max Guests: 4Bedrooms: 1Bathrooms: 1.5Type: HomeLocation: Key West
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel th......

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  • Non Smoking

Key West Oceanfront Condo - 'The Sea Jay'

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
The condo is quite large at over 1100 square feet and looks directly at beautiful Smathers Beach. The 'Sea Jay' is located in La Brisa which is a gated community. It features a very large master bedroom with dressing room and a full bathroom. W......

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  • Handicap Accessible
  • Non Smoking

$1250 - $2500 per week *
2br - Two beds in Key West

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Lovely two bedroom, two bath home in Key West. Two blocks from beach. Secluded private pool. Extensively landscaped. Quiet street. Recently remodeled home includes modern kitchen, flat screen TV, high speed internet with WiFi. All linens. Rear deck with chairs and table for breakfast/dinner that overlooks the pool. Central air/heat. Address: 1709 Josephine, Key West, FL Prices Season: Jan/Feb/Marc...

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$425 per night *
DIRECT OCEANFRONT FREE WIFI & HBO

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: CondoLocation: Key West
! Nothing between our balcony and the ocean except 20 yards of sand! Free high speed wireless Internet! This very upscale unit is one of the largest in this tropical complex with over 2000 square feet living space. There is a wrap around deck wh......

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  • Non Smoking

Oceanfront Condominium - Key West's Crown Jewel

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
We know that you will enjoy staying in our little bit of paradise - our home away from home - Key West's Crown Jewel. This is a two-bedroom, two-bath, penthouse condominium with 1350 square feet of living space. Enjoy absolutely breathtaking ocea......

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  • Non Smoking

$1500 - $3154 per week *
Crowner's Jewel

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome. Lots of space with for a family of 6. Master bedroom has bath ensuite and private balcony. Living room opens to......

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  • Non Smoking

$225 - $435 per night *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished with all attention given to your comfort and convenience. The tranquil tropical setting will make you ...

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2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$4000 - $5333 per month *
1214 Packer St

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
This charming 2 bedroom, 1 bathroom house is conveniently located. Just a short distance from downtown/Duval Street, restaurants and major attractions. Fully equipped kitchen, 1 king bed, 1 queen and 1 sleeper sofa. This home is cared for by a l......

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  • Non Smoking

$1100 - $2320 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
KEY WEST CHARMING at the Shipyard Condominiums. This downstairs 2 bedroom 1 bath home has been lovingly cared for by the owners. They actually use the property themselves each spring so they know what will make their guests stay more comfortable. The living and dining area open out to the large back wooden deck that is one of the best spots on the island to relax and soak up the sun in privacy, or...

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$1200 - $1950 per week *
Tropical and lovely, charming condo located on quiet walking lane.

Max Guests: 5Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Our Key West condominium, Lazy Lane, is a tropical 2 bedroom, 1 bath, 2nd floor condominium. The master bedroom has a queen size bed, and 2 twins in the 2nd bedroom, and also includes a sleeper sofa in the living room. French doors off the living ......

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  • Non Smoking

$9000 - $17500 per month *
“HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Old Town Home + Pool & S

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
In the Historic Seaport area of Old Town, there is a house that is very attractive from the street, beautifully maintained with carefully tended landscaping. However, nothing will prepare you for what is inside. As you walk in, you will feel an im......

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  • Non Smoking

$150 - $320 per night *
La Brisa #302E Tropical Tranquility

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roo......

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  • Non Smoking

$175 - $280 per night *
Affordable Luxury Beachfront Condo with Olympic Pool, Tennis Courts, S

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Enjoy all the amenities at 1800 Atlantic Condominiums without breaking the bank! Our island view condo sleeps 4-6 and has everything you need for your tropical vacation. The condo is located only steps from Smather's Beach, which is the largest be......

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  • Handicap Accessible
  • Non Smoking

$2150 - $2350 per week *
Truman Annex - Foundry Townhouse - One of a Kind!

Max Guests: 4Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Once you see this roomy two storey townhouse, you won’t want to stay anywhere else! Filled with natural light, this end unit is ‘tucked away’ in an exclusive and historic building next to the ‘Truman Little Whitehouse’. The oversize clay brick pat......

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  • Non Smoking

$200 - $450 per night *
Luxury Key West Condo -All New Plus So Much More---- 8 Bikes Included

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
Condo located less than 1/2 mile outside of Key West in new gated community in Stock Island. 1100 sq. ft, beautifully decorated in Key West style. Spacious, clean with granite counter tops through out kitchen and baths, stainless appliances, Jacu......

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  • Non Smoking

3 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
3-night minimum rental. Marvel at the topaz Caribbean view through every window of your vacation paradise at King's Pointe?s world-class marina. Share Atlantic sunrises with blue heron, pelicans, and other exotic tropical birds from your peaceful, private verandah overlooking Boca Chica Channel. At the end of the day, you can sip margaritas as you watch a fabled Key West sunset poolside from the w...

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  • Non Smoking

$270 - $400 per night *
Key Lime Calypso

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers......

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  • Non Smoking

$5500 - $6933 per month *
The Palms

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a f......

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  • Non Smoking

$2610 - $4200 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed residence, custom finished with classic sophistication and appointed with every modern convenience. Walk a few blocks to fabulous dining and shopping opport...

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1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

One of a kind estate in the heart of old town Key West!

Max Guests: 6Bedrooms: 3Bathrooms: 1Type: TownhouseLocation: Key West
Experience the uniqueness of Key West by staying at one of Key West Hideaways one of a kind vacation rentals. When you're ready to escape the hustle and bustle of the real world why not enjoy the perfect alternative to a pricey luxury hotel. Our p......

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  • Pet Friendly
  • Non Smoking

$6000 - $7000 per month *
Island Couture ~ a modern island bungalow

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Irresistible modern home renovated & decorated in simple island style. Desirable single level floor plan & natural light with oversized windows, covered patios and floor to ceiling glass doors. Enjoy a fabulous combination of function & design tha......

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  • Non Smoking

$245 - $380 per night *
Tom's Parrot Perch: GUT RENOVATION COMPLETED 9/16/11!!

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Located only two minutes from the airport and five minutes from downtown the area truly offers the best of both worlds, close to downtown without the noise. 1800 Atlantic sits on 400 feet of oceanfront property. An Olympic sized heated pool and sp......

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  • Non Smoking

$4000 - $7000 per month *
Tropical Serenity

Max Guests: 2Bedrooms: 1Bathrooms: 1.5Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been completely restored to a pristine condition. A large front yard wtih quaint front po......

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  • Non Smoking

$2940 - $5390 per week *
3br - Casa Margarita

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport is just steps away with many restaurants, boating activities, historic sights & shops to keep you busy all day! Behind the front fence of the property you can park your car and leave the world behind as you step through the tropical foliage to enter the home from the...

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  • Non Smoking

$8000 - $18000 per month *
'CIELO TROPICALE @ CASA EAST': 4BR/4BA Pavilion-Style Home with Large

Max Guests: 10Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
THE LIVING AREA: The entire living area of this home can be opened to the outside, thanks to 9 sets of French doors, and with the high vaulted ceiling, there is truly a sense of open airiness in this pavilion style tropical home. You'll enjoy plen......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$5000 - $7500 per month *
Olivia Cottage

Max Guests: 4Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's hist......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$2500 per month *
Casa de Suenos (House of Dreams)

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Delightful in every way describes this hidden gem located in the Meadows area of Old Town Key West. This is a one bedroom, one bathroom charmer with an additional queen size sleeper sofa in the living room and a pool. The chef will love the gour......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$5000 - $6500 per month *
A Quiet Vacation Experience in a Lush, Private Bungalow

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Pristine Old Town cottage with a little bit of everything including 3bd/2ba + delightful outdoor bath, 2 off street parking spaces, heated pool with waterfall & private spa. An outstanding use of space brings the outdoors in with the family room n......

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  • Non Smoking

$260 - $420 per night *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living roo...

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$950 - $1200 per night *
'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private D

Max Guests: 14Bedrooms: 5Bathrooms: 4Type: TownhouseLocation: Key West
This beautiful 5 bedroom 3500 sq ft town home is located directly on the water at Garrison Bight, with direct access to Florida Bay. 'Paradise @ The Bight' has everything you'll need while you're in Key West: luxurious accommodations, a dramatic ......

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  • Handicap Accessible
  • Non Smoking

$1750 - $2750 per week *
Key West - Truman Annex Cottage-Best Location on the Island-Newly Reno

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: TownhouseLocation: Key West
Pelican's Perch is conveniently located within walking distance to most everything in Key West. It has been remodeled with new paint, furniture and art. New pillow top mattresses too! In fall of 2011 we completely remodeled the Kitchen and baths. ......

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  • Non Smoking

$4500 - $8500 per month *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL From the owners of South of Frances here is another beautiful restoration of a Key West historic property. This lovingly restored home is ready for guests following a complete redo! The attention to detail and master craftsmanship is everywhere in this beautiful house.. The first floor of the home features a den/TV room with built in queen size Murphy bed highlighting the dad...

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The Golden Heron

Max Guests: 12Bedrooms: 5Bathrooms: 4Type: HomeLocation: Key West
The Key West Golden Heron is a Gold Star Landmark home, walking distance to the beaches, shopping and famous Duval Street, yet quietly situated in Old Town. One of the most spacious and charming high-end homes on the island, the Golden Heron has......

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  • Pet Friendly
  • Non Smoking

$7000 - $15000 per month *
'LA CASA AZUL @ SOLARES HILL': Elegantly Renovated 3BR/3BA Home + Heat

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
From the street, 'La Casa Azul' is a charming conch home, but it's only when you enter that you will realize how much home is hidden behind its pale blue walls. There are hardwood floors throughout. In the living room, the ceilings have been pains......

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  • Pet Friendly
  • Non Smoking

$2200 - $4000 per month *
Namaste Key West - Tropical Retreat in a Key West Conch Cottage

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CottageLocation: Key West
Key West has all of the charms of being away from the world, yet with all of the worldly conveniences near at hand. Located in the historic old town, Namaste Key West is in a quiet residential neighborhood, with beaches 5 minutes away, 3 yoga stud......

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  • Pet Friendly
  • Non Smoking

Toon Hall

Max Guests: 10Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom h......

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  • Non Smoking

$465 - $750 per week *
'Wonderful Villa, we loved it' Mrs. Lee Aug 2010. COUPLES DISCOUNT

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: VillaLocation: Key West
***FANTASTIC NEW BATHROOMS ***This luxurious villa is situated in the Los Molinos community. Our 2 bedroom 2 bathroom air-conditioned villa is built on 2 levels, with the bedrooms downstairs.Master bedroom has double doors leading out to the rear ......

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  • Pet Friendly
  • Non Smoking

$300 - $350 per night *
Pelican Landing Antigua Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$200 per night *
2 br Key West Condo Vacation Rental - Ocean nearby

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
"TEE BY THE SEA" vacation rental (we include 6 bikes free for our guests!!!) If you love...GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT...than you'll love "Tee by the Sea". We're less then 1/2 mile outside of Key West, located in Stock Island. Our condo is in a new gated community with only 52 units that boasts a beautiful heated pool, lush landscaped grounds, fitness ...

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  • Non Smoking

Tropical Hideaway

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Lush gardens surround this lovingly restored two-story Bahamian house. This downstairs suite has one bedrooms with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, wireless internet and a private ......

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  • Non Smoking

$700 - $1050 per night *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, french doors opening up to the porch and lushly landscaped garden/pool area. The two b...

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$150 - $275 per night *
Coral Suite

Max Guests: 6Bedrooms: 2Bathrooms: 3Type: CondoLocation: Key West
CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 3 bath townhome accommodates up to 6 people, and your pet! Both bedrooms (ensuite) are on ......

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  • Non Smoking

$1400 - $2660 per week *
2br - Vista Fresco

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits Oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or barbeque in the shade of this beautiful garden. When you are done relaxing by the pool,...

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  • Non Smoking

$9000 - $14000 per month *
'KOI HOUSE @ SOUTHERNMOST': 5 BR/5BA Compound with Courtyard, Koi Pond

Max Guests: 12Bedrooms: 5Bathrooms: 5Type: HomeLocation: Key West
Located on a quiet little cul-de-sac not far from the Southernmost Point in the Uptown part of Key West, you will find Koi House, a very private residential compound with its own meandering pond filled with Koi fish, a huge courtyard and a Japanes......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$1300 - $1950 per week *
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
A unique feature of this property is bicycles! Key West is only two miles by four miles, so nothing is very far away. Fly into the Key West airport and take a cab to Truman Annex You have bicycle transportation throughout your vacation. Big basket......

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  • Non Smoking

$6800 - $10000 per month *
Large and Private Waterfront Luxury Living

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Key West luxury and elegance marks this beautiful two level waterfront luxury property. This is a brand new house, with marble floors throughout (no carpet!), and a minimalist décor. Offering the best of Key West style, this spacious house has 4......

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  • Pet Friendly
  • Non Smoking

$290 - $460 per night *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, or shopping on Duval Street. Better yet, it is just three blocks to a beach (Duval & South Streets). This house can comfortably sleep four and offers a fully equipped kitchen, two bedrooms, living area with outside dining, BBQ and a small pool. The open style living and dining area has a c...

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  • Pet Friendly

$1100 - $2320 per week *
Parrot Perch

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this home is in a great location and a great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room ......

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  • Non Smoking

$2900 - $4900 per week *
Luxurious 4 bedroom/3 full bath home with private pool in Old Town Tru

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: TownhouseLocation: Key West
Enjoy all the charm Key West has to offer in this beautiful, newly renovated 4 bedroom/3 full bath house with private heated pool in the heart of Old Town. This home has ample room for relaxation and enjoyment. Located in the gated community of Tr......

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  • Non Smoking

$4000 - $9200 per week *
3 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 3Bathrooms: 4Type: HomeLocation: Key West
EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance hides the cozy, casual ambience you feel as you walk through the house and out to the bricked yard with o...

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$268 - $328 per night *
Southernmost Retreat: 1 Block from Duval in Old Town. Blocks from the

Max Guests: 6Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded b......

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  • Pet Friendly
  • Non Smoking

$300 - $350 per night *
Pelican Landing Curacao Retreat

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$6000 - $6500 per month *
HGTV Featured Home - Boaters Paradise! Waterfront Key West Home

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Boat in, boat out. Inspired by Balinese design this private waterfront retreat has deep-water access and is the ultimate base for the ocean enthusiast. Choose to escape, relax and meditate by the waterfall or head out for a day of adventure on the......

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  • Pet Friendly
  • Non Smoking

$700 - $1000 per night *
Old Town Key West by Southernmost Beach and Duval Main Street.

Max Guests: 12Bedrooms: 5Bathrooms: 4Type: HomeLocation: Key West
Prime Old Town Walking Location. Across the Street from Southernmost on the Beach, and down the Street from the Southernmost Point. No need for a car but we do have parking. Large outdoor swimming pool. Balcony seating areas to watch the world......

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  • Non Smoking

2br - Paradise Key West Condo

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This is a non-smoking condo/hotel(you may smoke on the balconey), that "home away from home" comfortable appeal, reasonably priced 2 bedrooms(1 king/1 queen/sofabed-linens provided) plus 2 full baths with a fully equipped kitchen (dine in/dine out), cental air with free parking on site. There is concierge service, maid service-extra fee, outdoor lagoon-shaped pool with spa, fitness center, tennis ...

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$3500 - $5000 per week *
Southernmost Escape

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
A classic 3 story Key West style town home that features 3 Bedrooms 3 1/2 Baths, custom made traditional pine wood floors, Beautiful Cherry Cabinets with black granite counter-tops in kitchen and baths, Viking appliances, tumbled marble showers an......

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  • Pet Friendly
  • Non Smoking

$340 - $682 per night *
Tropical Dreaming

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
TROPICAL DREAMING -- This tropical 2-bedroom home has been professionally decorated and furnished. There are classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. Many large windows frame ......

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  • Non Smoking

$270 - $480 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. It has central heat/air, cable TV, washer/dryer, well-equipped kitchen, 2 baths, security entry and elevator access. There is one reserved covered parking space. Resort ...

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Serendipity, Serenity and Simplicity--Call and ask about our special

Max Guests: 3Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Please Call Marilyn at 614-746-4702 from 9:00am to 10:00pm eastern std time. You will love staying in this great location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm, friendly and d......

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  • Non Smoking

$3200 - $5100 per month *
1 br Key West Home Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 2Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale for an extended stay vacation. This charming one bedroom bungalow has it all, queen sized bed and bath e...

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$1100 per week *
Pink Iguana - Beautiful Fairway View...Location...Location

Max Guests: 6Bedrooms: 2Bathrooms: 1.5Type: TownhouseLocation: Key West
The neighborhood is beaming with colorful Conch style, white picket fenced homes, lush tropical plants, resort style tranquil pools, fitness center, quiet nature filled walk areas and a wonderful 18-hole Reese Jones designed golf course complete w......

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  • Non Smoking

'Coral Isle' Beautiful 3Bed/3Bath Two Story Townhome at Coral Hammock

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: TownhouseLocation: Key West
I am excited to offer our most recent addition of reasonably priced gorgeous homes located at Coral Hammock. Built in 2004, this home is part of a gated community of 55 luxury resort homes with a lavish Clubhouse available for rental, Pool and lus......

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  • Pet Friendly
  • Non Smoking

$5200 - $8000 per month *
3br - Brass Palm Villa - Key West Home

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has to offer, as well as a short stroll to Higgs Beach, White Street Pier and Duval Street. The location is perfect to relax & stay a...

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  • Non Smoking

$200 - $370 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium complex is situated opposite the largest beach on our tiny island of Key West, Smathers's Beach, while offering many amenities of a resort hotel. Sunbathe next to a large kidney shaped pool, with beautiful, tropical landscaping. Soak in the adjacent hot tub after a long match of tennis on La...

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$550 - $864 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 4Type: HomeLocation: Key West
Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Keys style, this spacious townhome has 3 bedrooms, 3.5 baths and is situated in a quiet Meadows residential neighborhood, still just 12 blocks from Duval St. Overlooking the scenic Garrison Bight Marina the home boasts a private boat slip, patio area with ...

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$2800 - $5500 per month *
'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: VillaLocation: Key West
Poolside Retreat is a private two-story villa nestled in the lush tropical landscaping that surrounds the gorgeous resort-style private pool in the Key West Country Club. Your back yard gate will be just steps from the pool's edge. The neighborhoo......

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  • Pet Friendly
  • Non Smoking

Poolside Paradise

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
Where else can you find resort style accommodations at motel pricing? Poolside Paradise, one of our most popular properties, features all the luxuries of high end vacation rentals at an affordable nightly rate. Once the winter vacation suite of Pu......

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  • Non Smoking

Key West - Poolside Conch Paradise at Key West Golf Club

Max Guests: 4Bedrooms: 2Bathrooms: 1.5Type: TownhouseLocation: Key West
This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable and relaxing. There are porches on both floors, front and rear. Paddle fans throughout, along with high ceilings and......

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  • Non Smoking

$3000 - $4000 per week *
Bahama Gardens - Private Historic Old Town

Max Guests: 8Bedrooms: 4Bathrooms: 1.5Type: HomeLocation: Key West
The 'Main House' is a 2 story, 4 bedroom 1.5 bathroom renovated historic home. The house can accommodate 8 guests - 1 queen bed, 1 full bed, 3 twin beds, and 1 queen sleeper sofa; wrap-around upper balcony, & wrap-around porch, overlooking the......

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  • Non Smoking

The 'Old Town Eyebrow' - Located in the sought-after historic section!

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Welcome to your new Key West vacation rental home! A newly renovated two-story classic eyebrow style home with the original dade country pine and hardwood floors throughout. The decor and furnishing have been hand selected by a local designer with......

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  • Non Smoking

For Rates Contact Owner
Modern Luxury and Privacy Just Steps from Duval

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Would you enjoy truly modern luxury within walking distance to Key West's best restaurants, clubs, and art galleries? If so, this is the vacation house for you! It is brand new and open for reservations....

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  • Non Smoking

Little Palm

Max Guests: 2Bedrooms: Bathrooms: 1Type: CottageLocation: Key West
LITTLE PALM - What an idyllic setting! Picture a new cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off by ......

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  • Non Smoking

$3500 - $5333 per month *
The Pearl in Paradise

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offer......

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  • Non Smoking

2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Located in Old Town, This home is conveniently located within walking distance to the Seaport, restaurants, and major attractions. The house has 2 bedroom 2 bath and a nice backyard with a pool. Bedding Configuration: 1 Queen, 2 Other Additional Features: * Entertainment: Cable TV, CD Player * Geographic: Downtown, Near Beach * Kitchen: Full Kitchen, Microwave * Living: Central Air Conditioning, C...

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  • Non Smoking

$5500 per month *
HISTORIC RESTORED 'EYEBROW' HOME. SPECIALS AVAILABLE!!!!!

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
This Historic home was built in 1895 and lovingly restored in 2001.This is one of only two eyebrow style homes in Key West that have a front dormer in the roof for architectural appeal. Although this home is an historic treasure, it is fully equip......

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  • Pet Friendly
  • Non Smoking

3 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Coral Hammock is one of the newest gated communities with 55 luxury resort homes with a lavish Clubhouse, Pool and lushly landscaped grounds. These custom single family homes recall the romantic charm of old Key West with spacious floor plans, vaulted ceilings, "Conch" style porches and the traditional metal roof. Located at "mile marker 5" and ideally located across from the Key West Golf Club an...

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  • Non Smoking

$2000 - $3750 per month *
'CONCH CASITA 3 @ ELIZABETH': Immaculate 2BR/1BA Conch Cottage in Old

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
'Conch Casita 3' is a small home, but everything inside has been designed with the same efficiency as a ship's cabin. The living area includes a comfortable recliner, a full sized sofa, flat screen TV and iPod compatible stereo system. Three lar......

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  • Pet Friendly
  • Non Smoking

$150 - $200 per night *
Pelican Landing Curacao Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$8500 - $15000 per month *
GRAND 4 BR HOME, Ideal Location, Reduced Rates May thru June, Only $7,

Max Guests: 8Bedrooms: 4Bathrooms: 3.5Type: HomeLocation: Key West
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, ......

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  • Pet Friendly
  • Non Smoking

Catch of the Day - Gorgeous waterfront townhome, bring your boat!

Max Guests: 6Bedrooms: 3Bathrooms: 1Type: TownhouseLocation: Key West
This luxurious 4 level waterfront townhome is located on Garrison Bight in Old Town Key West. The home features high ceilings, maple and slate floors, a private elevator and an open floor plan with breathtaking views from most rooms. The kitchen ......

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  • Non Smoking

Cheerful Truman Annex Home

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: TownhouseLocation: Key West
A beautifully furnished and comfortable town home, located within the prestigious President`s Walk at Truman Annex. The first floor includes a covered porch, living room, dining area, full kitchen and a full bath. The second floor is outfitted ......

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  • Non Smoking

$1100 - $2538 per week *
Finn Key

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
FINN KEY: A beautiful 2 bedroom 1 bath downstairs condominium located in the Shipyard section of Truman Annex, a gated residential community in the heart of historic Old Town Key West. This lovely home has all the comforts including flatscre......

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  • Non Smoking

Southern Cross

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story conch cottage, surrounded by exotic gardens, situated in the......

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  • Non Smoking

$8500 - $10000 per month *
Orchid Oasis - Spacious home near the historic Sea Port.

Max Guests: 10Bedrooms: 4Bathrooms: 2.5Type: HomeLocation: Key West
Classic Old Town Key West home boasting rare combination of LOCATION, CHARACTER & SPACE. A meticulous restoration of historic details evident throughout paired with the ease of two of almost every amenity situated on two floors of a single family ......

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  • Non Smoking

Key West Boat & Breakfast, Reef Sailing Trips, Island Trips

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: YachtLocation: Key West
Located in Key West's Historic Seaport, choice of two sailboats for your dockside lodging. Your stay/sail charter includes 2 hour sunset sail/2 night package or half day 4 hour sail with a 3 night stay, snorkeling at the reef with equipment, capta......

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  • Non Smoking

$1200 - $2610 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
*** ASK ABOUT OUR SPECIAL MONTHLY RATES AVAILABLE FOR SUMMER 2012 *** SHIPYARD TREASURE - Great Key West location, this two bedroom one bath Shipyard condo has it all. You are centrally located to all the sites and attractions of Old Town Key West and the beach at Fort Zachary Taylor State Park. Located in the Truman Annex this property has a shared pool, off street parking and 24 hour security. S...

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$348 - $448 per night *
4br - Bone Island Vacation Rentals Seaport Suite

Max Guests: 10Bedrooms: 4Bathrooms: 2Type: ApartmentLocation: Key West
This downtown Key West vacation rental is one block off Duval Street, just around the corner from Sloppy Joe's and convenient to EVERYTHING! Located at the party end of Duval, within walking distance of the Historic Seaport and Mallory Square for sunset celebration. If you're looking for the perfect location in old town and want to be close to Duval Street then look no further. This is absolutely ...

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  • Non Smoking

Affordable, Charming, Quiet, Walking Distance to Town, Shopping, Dinin

Max Guests: 3Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Tree Tops is a stylish and practical one bedroom condo located in the gated community of Truman Annex. Truman Annex is a popular and beautifully landscaped community in the heart of Old Town Key West. Situated just two blocks from the popular Duva......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony with a lovely view of the Key West Harbor from the spacious 2nd floor deck. In case you would like to work on vacation the unit has a wireless DSL connection. There is one assigned parking space per unit. Enjoy a dip in the pool, a quick walk to Ft Zachary ...

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  • Non Smoking

$8820 - $12500 per month *
2012 Special Pricing Hemingway Style Cottage/Tropical Pool

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: CottageLocation: Key West
Just pack your shorts and sandals, your Jimmy Buffet CD's, pick up a Hemmingway book, and head for this fantastic 3 bedroom, 2 bathroom abode in the heart of Key West. When you walk through the 15' high groomed hedge gateway you are in the front......

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  • Pet Friendly
  • Non Smoking

2 br Key West Apartment Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: ApartmentLocation: Key West
This townhome home has a den, master bedroom with a queen bed and full bathroom on the first floor as well as a stackable washer/dryer unit. The second level has a living room, dining area, kitchen, half a bathroom and a balcony with a grill. From the second level there are stairs so you can access the walkway to the pool. Take the spiral staircase up to the third level to the loft that has two tw...

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  • Non Smoking

$595 - $1183 per night *
3 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Bahama House - Location, Location, Location! Brand new and totally gorgeous, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only one block from the fabulous shops, activities, restaurants and nightlife on Duval Street. Beautifully furnished and luxuriously appointed, Bahama House has three bedrooms, all with private baths, graciously spread out over...

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$325 - $450 per night *
'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master S

Max Guests: 6Bedrooms: 2Bathrooms: 3Type: HomeLocation: Key West
This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that 'Puerta Coralina' reflects the simpler sid......

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  • Pet Friendly
  • Non Smoking

Key West Waterfront Rental

Max Guests: 16Bedrooms: 9Bathrooms: 4Type: HomeLocation: Key West
Welcome to Our Vacation Home! This property has been our Family Vacation home since we built it in 1978 and we are Happy to share it with you. All the plants were put in the ground by us, many have survived Hurricanes. Please Respect The Other G......

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  • Pet Friendly
  • Non Smoking

2br - Sailor #039;s Quarters

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
This Historic Register property enjoys a superior location in the Heart of Old Town - an easy 4 block walk from historic Duval Street, the center of Key West’s vibrant night life. It is located at 522 Margaret Street between Southard and Fleming Streets 2 doors from Michael’s Restaurant and a half block from Mangia-Mangia, two of Key West’s most popular restaurants. It is at the rear of a 135 foot...

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  • Non Smoking

$210 - $392 per night *
1 br Key West Home Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
ISLAND PEARL: True island living in this 1 loft bedroom 1 bath cottage, complete with living room and kitchen. French doors open to a meandering deck surrounded by tropical foliage. This secluded hideaway is located behind a needlepoint store in historic Old Town Key West. Enter the gate beside the store and you have arrived at your own private oasis with winding walkway to the blue pebbled pool a...

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$155 - $348 per night *
Paradise Place

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
PARADISE PLACE – is a ground level one bedroom one bath condominium located in the Palm Gardens community in the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Paradise Place is part of a group of histor......

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  • Non Smoking

$150 - $275 per night *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
CORAL CARIBE: Located in the Coral Hammock community, this lovely 2 bedroom 2.5 bath townhome with sleeper sofa is in the perfect spot, directly in front of the shared pool where you can spend your days sunning and swimming to your heart's content. Equipped with all the modern conveniences, you will feel right at home relaxing on your private balcony sipping pina coladas or grilling burgers or you...

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$1550 per week *
Stock Island Waterfront Condo with a Boat Slip

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Like Old Key West Your waterfront vacation place is in the most unique mixed use marina community in the Keys. Watch the fishing boats unload their catch. Walk the docks out of your front or back door with the yachts mixed in with the house boat......

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  • Pet Friendly
  • Non Smoking

$500 - $550 per night *
Pelican Landing St.Croix Retreat

Max Guests: 12Bedrooms: 4Bathrooms: 4Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$470 - $800 per night *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 3.5Type: HomeLocation: Key West
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. All bedrooms and two baths are located on the second floor. The dining area and kit...

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  • Pet Friendly

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$5500 - $12500 per month *
'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
In the heart of Old Town is a classic Conch House that has been completely renovated and updated while retaining all of its historic charm. Surrounded by lush tropical foliage with brick pavers leading up to the front door, this home is immediatel......

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  • Pet Friendly
  • Non Smoking

$150 - $200 per night *
Pelican Landing Aruba Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$2700 - $6500 per month *
Relaxing, quiet, get-away just blocks from downtown Key West & Beach -

Max Guests: 8Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
This newly renovated home is perfect for a family or group of friends who want to get away and become 'temporary residents' of the 'Conch Republic.' This warm, beautiful fully furnished home is set up so that you can simply bring your clothes and......

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  • Pet Friendly
  • Non Smoking

$4000 - $6000 per month *
3 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighbo...

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$160 per night *
2br - Tropical Escape

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This luxurious unit has 2 bedrooms (one king size, one queen size) plus 2 full baths and is a condo/hotel. There is concierge service. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The patio overlooks the gorgeous tropical pool and spa. The unit has WiFi, cable, 3 TV's, dvd, and a/c. On the premises is a pool, spa, laundry room, workout cente...

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  • Non Smoking

$3500 per month *
3br - Charming Old Town Home

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Now available for minimum 28 day rentals! Fully furnished three bedroom and two bath home. This home features off street parking, lush tropical landscaping, private yard and deck space, pool access, grill and a great front porch. Awesome floor plan with lots of space. Conveniently located steps from the White Street arts district in a very quiet neighborhood....

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  • Non Smoking

$710 - $1220 per night *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of mature palms, birds of paradise, flowering ginger and bromeliads surround a pool complete with gazebo an...

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$325 per night *
Stunning Brand New HOUSEBOAT in Paradise!

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: Location: Key West
Come stay aboard our BRAND NEW houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of 'members only' amenities including a swimming pool, private beach, tiki bar, fitness facility, ......

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  • Pet Friendly
  • Non Smoking

$1900 per week *
Truman Annex 2bed/1bath condo, premier downtown Key West location and

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Our 2bed/1 bath condo in the lovely gated community of Truman Annex provides the perfect way to experience Key West- like a local. It sits on a quiet lane away from the bustle, yet everything is in walking distance. There is a gated secure parkin......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$12500 per month *
Private House: A Peaceful Oasis

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
Description: Traditional yet stylish with careful attention to classic detail. Timeless elements throughout including 10ft ceilings finished in oversized moldings, marble and stone bathrooms and counters, wood floors and plenty of indoor and outdo......

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  • Non Smoking

$400 - $585 per night *
Luxury Waterfront at the Galleon Resort in Old Town

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, fully equipped kitchen, breakfast area, dining room, living room and the master bedroom & bath. The second floor has an open loft......

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  • Non Smoking

$160 - $280 per night *
Ann Street Cottage

Max Guests: 2Bedrooms: 1Bathrooms: 1.5Type: CondoLocation: Key West
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Town Hall, around the corner from Duval Street and offering 'walk......

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  • Non Smoking

$350 - $530 per night *
3 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This elegant 3 bedroom/ 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. The unit features central heat/air, cable TV, washer/dryer, well equipped kitchens, 2 baths, security entry, and elevator access. There is one reserved parking ...

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$150 - $200 per night *
Pelican Landing Harbor Island Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Non Smoking

Key West Cottage: Bahama House, Key West, FL, 33040

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CottageLocation: Key West
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch cottage. It is a perfect example of turn-of-the-century island architecture. This modest two bedroom cottage, each with queen bed and TV (the master has a large flat ......

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  • Pet Friendly
  • Non Smoking

$170 - $348 per night *
1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
PARADISE PLACE – is a ground level one bedroom one bath condominium located in the Palm Gardens community in the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Paradise Place is part of a group of historic homes which have undergone complete renovation. This lovely property offers hardwood floors and cabinets, granite kitchen countertop and beautifully ti...

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  • Pet Friendly

$250 - $471 per night *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot you know you are some place special. A small gated and secured compound with only 13 properties, this townhome community is quiet and private while still being located right in the heart of Old Town. With a limited number of properties you may feel that your neighbor is an old friend. Jus...

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$1600 - $3408 per week *
Key West Found

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
KEY WEST FOUND – A striking 2 bedroom, 2.5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper ......

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  • Non Smoking

$9500 per month *
Sophisticated Elegance on Fleming Street

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: HomeLocation: Key West
Constructed in 1859, this prestigious Key West home exemplifies elegant tropical living. Superb renovations in 2006-07 perfect the ideal haven for entertaining with modern convenience in the heart of Old Town. With the island's best possible loca......

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  • Non Smoking

$195 - $270 per night *
1br - Hidden Oasis in Key West 2 blocks from Duval St.

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
This hidden oasis is just a two block walk to Duval Street with all the action Key West has to offer. Take advantage of this quiet condo, fully equipped with everything you need to just RELAX and have Fun...Also the blender is waiting for your margaritas!!! The Heron is one of several of the Colony Condominiums in historic Key West, Florida (sleeps 4). A conch style cottage nestled in the heart of...

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  • Non Smoking

$4000 - $5333 per month *
Turtle Cay Spa

Max Guests: 6Bedrooms: 2Bathrooms: 3.5Type: CondoLocation: Key West
Located at the Key West Golf Course in the sancutary is this 2 bedroom 2 1/2 bathroom multilevel spa home. The outside private patio is wonderful for a morning paper and a dip in the spa. The home is beautifully decorated with an open floor plan f......

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  • Non Smoking

$2800 - $4400 per month *
Suite Caroline - Serenade

Max Guests: 2Bedrooms: 1Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed res......

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  • Non Smoking

$160 - $250 per night *
Casa Atlantica Studio

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
A spacious studio apartment and large deck make this the perfect romantic getaway, feast your eyes on the breathtaking views of the Atlantic Ocean. Enjoy complete privacy, bird watching, sun and fun, located next to the White Street Pier and nest......

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  • Non Smoking

$2500 per week *
Blue Lagoon

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: TownhouseLocation: Key West
Welcome to ''Blue Lagoon'' located in prestigious Truman Annex, in the President's Walk and Southard Street area. This luxurious 3 BR townhouse is 1 1/2 blocks from Duval Street and all of the Old Town Key West attractions. We are 1/4 mile from ......

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  • Pet Friendly
  • Non Smoking

$368 - $408 per night *
2br - Bone Island Vacation Rentals Havana Hideaway

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
The Beach Boys on one of their many trips to the Florida Keys (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in the best conch tradition and features two bedrooms en suite, and two and a half baths. The sp...

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  • Non Smoking

$458 - $758 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels. Each has it's own private garden with heat optional swimming pool. The open living /dining area fe...

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Rose Lane Villa - Grande, 1/2 block off Duval!

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The Villa Grande is g......

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  • Non Smoking

$950 - $1550 per week *
My Condo by the Beach with Ocean View

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This is not a hotel; it is a privately owned condo f......

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  • Non Smoking

$5500 - $7900 per month *
Margaux's Hideaway - Spacious Private Tropical Home with Pool - KEY WE

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
This elegant two-story island home is a quiet retreat in the heart of Old Town Key West. Margaux's Hideaway is stylishly decorated, perfectly highlighting the classic nature of a Key West home while integrating modern amenities. This home is desi......

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  • Non Smoking

$270 - $480 per night *
Beach Club #103

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features a largee oceanfront balcony accessed from both the living/dining area and master bedroom. The unit......

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  • Non Smoking

$160 - $313 per night *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dinning area, full kitchen and a spacious bedroom with a king size bed. There is a nice private deck overlooking a tropical garden area , large shared swimming pool and a small fish pon...

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$350 - $500 per night *
Spacious Ocean Front Resort - 3 Bedroom Condo

Max Guests: 8Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
This 2, 000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on op......

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  • Handicap Accessible
  • Non Smoking

$7000 per month *
Tropical Reatreat!

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
Came and stay for month or more in our charming hideaway while you experience the magic of Key West. We make your vacation memorable experience.The beautifully landscaped backyard is gated and private with a heated pool, waterfall and guest house, ......

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  • Pet Friendly
  • Non Smoking

Beautiful Retreat in Key West Area

Max Guests: 12Bedrooms: 5Bathrooms: 3.5Type: HomeLocation: Key West
Our beautiful home is located on the bayside in Big Coppitt Key. Wake up in the morning to stunning views of the bay. The house is located in over 2 1/2 acre lot with room to park an RV and boat with trailer. The property is at the end of the stre......

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  • Non Smoking

$1000 - $1700 per week *
Restored luxury villa, private pool in idyllic countryside in Umbria/T

Max Guests: 8Bedrooms: 4Bathrooms: 3Type: VillaLocation: Key West
Capanna, a luxury villa, is based on a watch tower four centuries old. Two tobacco barns were added later. It is built in an area designated as one of outstanding natural beauty. Etruscan sites are nearby. The villa has been converted to a high ......

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  • Pet Friendly
  • Non Smoking

Old Town Truman & Duval Townhome

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Large secluded Old Town Conch-Style town home is located on Truman Avenue just one block from Duval Street. First floor has a bedroom with a private bath, fully equipped kitchen, dining/living room with cathedral ceilings and 2 sets of French door......

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  • Non Smoking

$458 - $758 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels. Each has it's own private garden with heat optional swimming pool. The open living /dining area fe...

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This 2003 Hunter Sailboat

Max Guests: 7Bedrooms: 2Bathrooms: 2Type: YachtLocation: Key West
Stay aboard a beautiful sailing yacht with all the amenities of home. I can arrange packages for you to include sailing, diving, snorkeling and kayaking...

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  • Pet Friendly
  • Non Smoking

$3000 - $4600 per month *
Luxurious Garden Home Paradise with Pool in Midtown Key West

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered outdoor pavillion with an entertai......

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  • Non Smoking

Downtown Key West Pool Home

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Jimmy Buffett) stayed at Havana Hideaway and wrote the song Kokomo - according to a very reliable source at the Pink Cab Company! This vacation home is a modern two-story, built in the best conch tradition and features two bedrooms en suite, and t......

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  • Pet Friendly
  • Non Smoking

$368 - $468 per night *
3br - Bone Island Vacation Rentals Island Oasis

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CottageLocation: Key West
ISLAND OASIS: Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West Hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been transformed with bits and baubles from around the world - carved headboard from Thailand, bed from Costa Rica, and the locally sculpted Spoonbill standing on...

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  • Non Smoking

$150 - $200 per night *
Pelican Landing Flamingo Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

Key West 3 Bedroom Condo- Direct Beach Front

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
Our 1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms and living room. There's a feeling of peace that engulfs you as you sit out on the deck over looking the aqua-blue water. Birds of various types, boating......

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  • Handicap Accessible
  • Non Smoking

$6500 - $8000 per week *
Beach house exclusive private resort island 500 yards from heart of Ke

Max Guests: 6Bedrooms: 3Bathrooms: Type: HomeLocation: Key West
Beach front private residence on Sunset Key Island. Spectacular open water views, with a private beach side pool make this exquisite residence a dream come true. Located in the heart of Key West Harbor, only four minutes from Historic old town Key......

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  • Non Smoking

$225 - $435 per night *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
CARIBBEAN DUVAL: Nestled above Duval St. in the heart of the Art district, in Duval Square, is this lovely 2 bedroom, 2.5 bath townhouse, “Caribbean Duval.” Located only 1.5 blocks from the historic Hemingway house, this gated, secure, spacious 1, 300 sq. ft. hideaway, features central A/C and an open floor plan with a half bath on the first floor and a full bath in each bedroom. The large master ...

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$8000 - $17000 per month *
'THE CORAL HOUSE @ THE SEAPORT': Lush 4BR/4.5BA Private Home w/Pool &

Max Guests: 10Bedrooms: 4Bathrooms: 4.5Type: HomeLocation: Key West
'The Coral House' is a historic home situated in the heart of Old Town, near the Historic Seaport. You'll be just steps from everything Key West has to offer, and yet you'll have the peace and quiet of being on Fleming Street. As you enter, you'll......

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  • Pet Friendly
  • Non Smoking

$200 - $340 per night *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Old City Hall, around the corner from Duval Street and offering 'walk to everything' convenience. This bright and airy cottage has tile floors thoughout, king sized bed, spa bath, a shared free form pool and washer/dry...

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$470 - $800 per night *
Amelia's Great Escape

Max Guests: 10Bedrooms: 4Bathrooms: 3Type: HomeLocation: Key West
Welcome to the Beach!!!! No this house isn't oceanfront! But in Key West almost anything is possible. This house has just been transformed into a relaxed beach house with many updates & upgrades. New furniture, cabinets and appliances as well ......

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  • Non Smoking

$200 - $370 per night *
La Brisa #306E Tropical Tuscany

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roo......

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  • Non Smoking

$2300 - $4900 per week *
'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block o

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: CottageLocation: Key West
'Casa Louisa' is a cozy and charming turn-of-the-century cigar cottage located in the center of the historic cigar-making district of old Key West, half a block from Duval Street on Louisa Street, a quiet lane that puts you within walking distance......

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  • Pet Friendly
  • Non Smoking

$210 - $380 per night *
Vista Fresco

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly land......

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  • Non Smoking

$4500 per month *
Beach Club Penthouse

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Enjoy the sights and scents of the Atlantic Ocean from this stunning penthouse located in the Key West Beach Club. Stylishly equipped with all of the necessities to comfortably sleep and entertain up to 6 people. The tranquil water view can be en......

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  • Non Smoking

$4800 - $11000 per month *
“LA CASA AMARILLA @ THE MEADOWS”: Unique 2BR/2BA Home on Quiet Old Tow

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: Location: Key West
In the Meadows, a neighborhood with some of the nicest homes in town, this exquisitely detailed home on Petronia Street is a hidden gem. As you come down this quiet little one-way lane, the lush landscaping that screens the front yard all but hide......

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  • Non Smoking

$1500 per week *
See & Hear Atlantic Ocean from Studio & King bed! ! Sunny! Beachy! See

Max Guests: 2Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
See BOOKED DATES- TRY for OPEN TIMES-love to have you! All rates stated are(no event or holiday) •Studio UP! ''The Best stay in Key West'' Magnificent ocean views, diamonds dancing on the sea, so close to heart of town. Like Nowhere Else! Ask f......

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  • Non Smoking

Truman Annex Three Story Townhouse ~ Private..Yet Close To Mallory Sq

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
'ABALONE' ~ This property rents for a minimum of one week [6 nights and seven days]. Located in a beautiful, tropical, gated community ....next door to Truman's 'Little White House'. This antique, Bostonian style Foundry Townhome is located just......

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  • Pet Friendly
  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2 twins and 1 pullout sofa. There is a balcony on the front and the back of the unit. The back balcony has a BBQ. The unit comes with one assigned parking spot. Bedding Configuration: 1 Queen, 2 Twin Additional Features: * Entertainment: Cable TV, DVD Player, internet, Stereo System * Geographic: Downtown, Near Beach * Kitchen: Fu...

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  • Non Smoking

$300 per night *
Ultimate Vacation in Paradise! Stay Right on the Water!

Max Guests: 4Bedrooms: 3Bathrooms: 2Type: Location: Key West
Come stay aboard the newest houseboat added to our fleet! Blue is a stunning 38ft catamaran docked in one of Key West`s most exclusive yacht club marinas. Our guests have free access to a host of 'members only' amenities including a swimming pool......

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  • Non Smoking

$2500 - $5000 per week *
“GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthous

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This beautiful penthouse condo is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You’ll have ocean views on three sides of your condo, and two spacious balconies as well....

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  • Non Smoking

$179 - $249 per night *
3br - Downtown Key West 3 BR Bahama House

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: ApartmentLocation: Key West
The Freeport Suite is a bright sunny, spacious 3 Bedroom centrally located only 1 block from the shops, restaurants, galleries and excitement of Duval Street. A great space for a family or a group of friends. The Freeport suite sleeps up to 6 guests. Recently renovated, each bedroom has a full-size bed and bright windows. 2 bedrooms overlook the serene, tropical garden. All of the bedrooms are air...

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  • Non Smoking

$200 - $300 per night *
Pelican Landing Andros Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1300 - $2610 per week *
The Hemingway

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to res......

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  • Non Smoking

$249 - $339 per night *
0br - 2p. w/ Beach 50ft! Paradise Vacation!

Max Guests: 2Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
We'd love to have you! All rates stated are(no event or holiday) •Studio UP! ''The Best stay in Key West'' Magnificent ocean views, diamonds dancing on the sea, so close to heart of town. Like Nowhere Else! Ask for photos!! GO' u' tube * then type 'oceanviewstudioinkw'. tennant isresponsible to point up our communiqué !Callers get the dates the fastest Off Season Apr 29-Nov 30 .$239-$289/night .. ...

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  • Non Smoking

$1900 - $3500 per week *
“COCONUTS @ THE DOCK”: 50-Foot 2.5BR/2BA Trawler at Key West Harbor Cl

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: YachtLocation: Key West
The M/V Coconuts is a completely unique home with 360 degree water views, located at 6000 Peninsular Avenue. It also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very c......

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  • Non Smoking

$460 - $790 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
A hideaway on Freeschool Lane This unique villa is hidden away on the end of the quiet lane just a step away from Duval Street. Surrounded by exotic tropical trees this contemporary hideaway is an island of serenity. Delight yourself in the sights and sounds of its lush tropical garden and the privacy of your lagoon shape pool. This two-story home, features all the amenities you desire for the per...

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$170 - $260 per night *
1 br Key West Ocean View Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled with a mixture of custom made furnishings and unusual objects from all parts of the globe, this centrally air conditioned one bedroom is truly unique. Spectacular decks, privacy, elegance and ocean breezes are yours for the asking. Bedding: 1 king A...

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$3500 - $4800 per month *
Boater's Dream

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Beautifully decorated with palm tree dé......

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  • Non Smoking

$600 - $800 per week *
Beachside holiday apartment, 'New Golden Mile’ near Marbella

Max Guests: 6Bedrooms: 3Bathrooms: 2.5Type: ApartmentLocation: Key West
3 bedroom, 3 bathroom ground floor air conditioned/warm air heating, under floor heated apartment. The apartment has been furnished with style and comfort with a touch of luxury for your enjoyment. Spacious large lounge/dining room with large fl......

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  • Handicap Accessible
  • Non Smoking

$1550 - $1850 per week *
'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier.

Max Guests: 6Bedrooms: 2Bathrooms: 1.5Type: HomeLocation: Key West
'Eden @ The Annex' is a charming townhome in Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, this home is on......

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  • Non Smoking

$1500 - $2200 per week *
Truman Annex: Paradise Lost Self Catering Unique ground floor condomi

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Paradise Lost' is a unique two bedroom, two bath, ground floor condominium located within the prestigious gated community of 'Truman Annex' in Key West's 'Old Town' area. This home boasts one of the longest patio decks (over 30 ft long) within the......

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  • Non Smoking

Architect's Personal Residence, Private Pool, 1 Blk. to Duval

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: Location: Key West
Completed in 1992, this two bedroom two bath home was designed by a local architect for the relaxed Key West tropical lifestyle. Located on a quiet old town street only one block from Upper Duval Street and Truman Avenue, it offers off-street par......

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  • Pet Friendly
  • Non Smoking

Tropical Village Cottage

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: CottageLocation: Key West
Tropical Village Cottage - is the epitome of modern Key West. This two bedroom, two bath conch cottage overlooks a shared oasis-style heated pool, sun deck and poolside grilling station. With all the amenities of contemporary living set in island ......

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  • Non Smoking

$1300 - $2610 per week *
Linger Longer

Max Guests: 5Bedrooms: 2Bathrooms: 1.5Type: CondoLocation: Key West
LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on ei......

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  • Non Smoking

Calypso Dreams: 4BR Home w/Private Pool, WiFi & Guest House in Florida

Max Guests: 12Bedrooms: 5Bathrooms: 5Type: HomeLocation: Key West
Bedding: 2 Queen, 1 King, 2 Twins, 2 Twins convert to King, Sleeper Sofa Description: \t\r This stately home sits on beautiful Noah Lane. The main house has 4 bedrooms and 4 full baths. The Master bedroom has a king bed with a bath en suite and s......

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  • Non Smoking

Henry's Piece Of Paradise On The Ocean In Key West (nightly / weekly)

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
1350 sq ft of fabulous living space located on the 2nd floor, with garden and partial ocean views from a 38 ft private balcony accessible from the living and both bedrooms, will make your vacation a memorable one and keep you coming back year afte......

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  • Non Smoking

2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Beautifully decorated with palm tree décor, leather sleeper sofa, warm colors to give you a feeling of being home. The unit has a master bathroom with a Jacuzzi bathtub and a separate shower. ...

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$710 - $1220 per night *
Villa Tropicale

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens ar......

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  • Non Smoking

$10000 - $11500 per week *
“NOONA'S MANSION-by-the-SEA @ THE ANNEX' 7BR/5.5BA Home with Pool...

Max Guests: 14Bedrooms: 7Bathrooms: 5.5Type: HomeLocation: Key West
Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate stands out from all the rest in every way. “Noona’s Mansion by-the-Sea' is nestled in a quiet cul-de-sac facing t......

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  • Non Smoking

$119 per night *
The Perfect Get-away in Paradise

Max Guests: 4Bedrooms: Bathrooms: 1Type: CondoLocation: Key West
The Galleria Condominiums, a wonderful, quiet retreat for a fun-filled and relaxing get-away! Each efficiency condo bears the name of a renowned artist, in salute to the artistic nature of Key West itself. The Claude Monet unit (Unit #3) is set a......

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  • Non Smoking

Seaport Suite - WALK EVERYWHERE!

Max Guests: 10Bedrooms: 4Bathrooms: 2Type: ApartmentLocation: Key West
Seaport Suite is available for daily rentals and is located on the second floor of the RE/MAX Southernmost building in Old Town, Key West. It's proud past includes; ships hardware store, a rooming house, and a long history of housing "entertainers......

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  • Pet Friendly
  • Non Smoking

Princess & the Pea - 3 bedroom townhome with private pool, 3 blocks to

Max Guests: 8Bedrooms: 3Bathrooms: 3.5Type: TownhouseLocation: Key West
Luxury & Sophistication are apparent as you enter this deluxe townhome, centrally located in a quiet Old Town neighborhood only 4 blocks from the heart of Key West, Duval Street. Over 1700 sq ft. divided between 2 levels with private garden & pri......

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  • Non Smoking

$380 - $700 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story historic home is beautifully decorated with warm tropical colors and features bamboo hardwood floors. This ...

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$1300 - $2610 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
CONCH CONDO -- This two-bedroom, two-bath condo was remodeled and completely refurnished in 2005. This second-floor unit features fully equipped kitchen, two full baths, top-quality custom furniture, plasma televisions and home theatre in living room, plasma televisions in both bedrooms, soaring cathedral ceilings with ceiling fans, new bamboo floors, central air conditioning, and plenty of closet...

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$280 - $420 per night *
Waterfront Luxury in Old Town Key West

Max Guests: 5Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen with new cabinetry and granite countertops, dining room, living room and a very sp......

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  • Non Smoking

$450 - $780 per night *
Pete's Cottages

Max Guests: 8Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
This property has it all! This award winning renovation offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each Twin opens to it's own......

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  • Non Smoking

$2000 - $2970 per week *
16th c. farmhouse with pool, beautiful gardens and views of Todi

Max Guests: 12Bedrooms: 5Bathrooms: 5Type: VillaLocation: Key West
The villa is furnished as a home from home – Gabriella has organised and designed the very welcoming feeling of the villa which is so much admired, including some lovely antiques and a 4 poster bed. The accommodation of some 300 M2 is very spaciou......

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  • Non Smoking

$1100 - $2538 per week *
Key West Charming

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
KEY WEST CHARMING at the Shipyard Condominiums. This downstairs 2 bedroom 1 bath home has been lovingly cared for by the owners. They actually use the property themselves each spring so they know what will make their guests stay more comfortable......

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  • Non Smoking

$1450 - $2450 per week *
Top-floor Smathers Beach condo with gorgeous pool, tennis and steps fr

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Beach, Bath & Tennis! La Brisa is a gated oceanfront condo located across the street from Smathers Beach - one of only a few white-sand swimming beaches in Key West. Miles long oceanfront walking/running/biking path. Community features beautiful ......

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  • Non Smoking

2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Coconut Mallory Resort and Marina by Kees Vacations 2 bedroom/2 bathroom premium condo Bedding Configuration: Unit bedding varies. Unit sleeps 6. Unit Description: This is a 2 bed/2 bathroom condo that features a full kitchen, washer/dryer, and a flat panel TV. The unit is decorated in an island inspired elegance and has a private balcony, access to both resort pools, and the resort marina. Overal...

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  • Non Smoking

$2500 - $3200 per month *
1br - Suite Caroline - Mandarin

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM. Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed residence, custom finished with classic sophistication and appointed with every modern convenience. Walk a few blocks to fabulous dining and shopping opportunitie...

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  • Non Smoking

Rose Lane Villa - Aqua, 1/2 block off Duval

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The Villa Aqua is gen......

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  • Non Smoking

$200 - $300 per night *
Pelican Landing Flamingo Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1300 - $2791 per week *
Beach House Condo

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
BEACH HOUSE CONDO: A beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex community. You will find everything here you want to make your Key West vacation spot a home away fr......

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  • Non Smoking

$1300 - $1925 per week *
Contemporary Condo at Truman Annex-Walk to Beach/Duval St.

Max Guests: 5Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Decorated in casual contemporary style, our second floor condo is newly-renovated, and centrally located in the Truman Annex, within quick walking distance to all the sites and attractions of Old Town Key West. Relax in 2 bdrms with queen beds and......

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  • Non Smoking

$1300 - $2610 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
BEACH HOUSE CONDO: A beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex community. You will find everything here you want to make your Key West vacation spot a home away from home and more. Beach House Condo has the perfect back deck to sip a cafe con leche in the morning, grill your own fresh catch in the afternoon and pamp...

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$870 - $2000 per night *
5 br Key West Ocean View Home Vacation Rental

Max Guests: 10Bedrooms: 5Bathrooms: 4Type: HomeLocation: Key West
There's a new place on Duval Street in historic Key West and it is unique! Dreaming On Duval premieres in early 2010 as the most luxurious single family vacation rental on Duval Street. Steps to everything Key West has to offer, this private home can accommodate up to 10 friends & family members for a relaxing vacation with everything you could ask for. This spectacular brand new home features fiv...

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2br - Two Bedroom Superior Suite

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: VillaLocation: Key West
Villas Key West is a small (7 unit) guesthouse located 200 feet from Duval Street! Our accommodations are apartments set in 2 old historic Key West houses joined by a deck and temperature controlled pool. The very heart of Old Town Key West within easy walking distance of everything. There is no better location in Key West… The 2 BEDROOM DELUXE VILLA was completely gutted and renovated in 2007. No...

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  • Non Smoking

$225 - $275 per night *
Ocean Paradise

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
3-night minimum rental. Marvel at the topaz Caribbean view through every window of your vacation paradise at King's Pointe’s world-class marina. Share Atlantic sunrises with blue heron, pelicans, and other exotic tropical birds from your peaceful, ......

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  • Non Smoking

Rose Lane Villa's Villa Alta 1 bedroom, 1/2 block off Duval

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: VillaLocation: Key West
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom villa......

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  • Non Smoking

$4000 - $7000 per month *
1 br Key West Home Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1.5Type: HomeLocation: Key West
30 DAY MINIMUM RENTAL An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been completely restored to a pristine condition. A large front yard wtih quaint front porch give this cottage the curb appeal of your dreams. Step in to the comfortable living room with Brazilian cherry floors and a white cotton sofa to relax...

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$260 - $420 per night *
2 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living roo...

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$4000 - $9200 per week *
Easy Livin'

Max Guests: 8Bedrooms: 3Bathrooms: 4Type: HomeLocation: Key West
EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll ......

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  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

Charming Key West townhome with all the comforts of home.

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
This townhome is located in the award-winning community The Truman Annex. The Truman Annex encompasses stately homes, luxury townhomes, and condos nestled amongst lush tropical gardens. Presidents Walk of The Truman Annex has a shared pool, 24-ho......

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  • Non Smoking

$180 - $370 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighborly and relaxing atmos...

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$1190 - $2380 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1.5Type: CondoLocation: Key West
In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard Condominium is great access to Zachary State Park Beach as well as the Historic Old Town Key West. This beautifully decorated first floor condominium on Southard Street has two bedrooms, one & half baths. The living room is nicely furnished with leather sofas, tv with DVD and high...

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2 br Key West Condo Vacation Rental

Max Guests: 8Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$150 - $200 per night *
Pelican Landing Bonaire Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
A delightful, deluxe one bedroom condo unit in the beautiful Southard Square complex. There's a king size bed in the bedroom and a sleeper sofa in the large and elegant living room. An entertainment island separates the kitchen from the living room and dining area. Southard Square offers a beautiful variety of large trees and native landscaping which catch the eye immediately. This landscaping enh...

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  • Non Smoking

$410 - $720 per night *
4 br Key West Home Vacation Rental

Max Guests: 8Bedrooms: 4Bathrooms: 4.5Type: HomeLocation: Key West
Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the action at Duval Square just south of Truman. The residential units sit in a courtyard setting above a retail/office courtyard below with the shared pool . There is no other condo like this at Duval Square. The penthouse home features a light and airy two...

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$150 - $200 per night *
Pelican Landing Florida Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

Charming, quiet, Old Town, walking distance to everything

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CottageLocation: Key West
PALM COURT - The Cottage: Sleeps Four - Our cottage is tastefully furnished with a mixture of antiques, oriental rugs and original art works. There is one bedroom with a queen size bed, one bath, and an upper sleeping loft with two single beds. Th......

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  • Non Smoking

$150 - $200 per night *
Pelican Landing Bermuda Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$2000 per week *
Hemingway's Hideaway Truman Annex

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: TownhouseLocation: Key West
Location, Location, Location, Best in Truman Annex, private yet has front deck plus deck off main bedroom. Near all major attractions. 200ft. from Little White House, shared heated pool, near Ft Zachary Taylor Beach. GATED COMMUNITY Off stre......

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  • Non Smoking

$225 - $275 per night *
BMW Fantasy

Max Guests: 6Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three b......

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  • Non Smoking

$100 - $500 per night *
Paradise Manor with private pool available May and June 2012

Max Guests: 9Bedrooms: 4Bathrooms: 2Type: HomeLocation: Key West
Beautiful and spacious house with private pool in quiet neighborhood. The house has a living room with TV, DVD, VCR, CD/radio, dinning room, fully equipped kitchen and laundry shade. The King's bedroom has a king size bed (can be 2 full-size) an......

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  • Non Smoking

Oceanfront

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront condominium set in a topical garden paradise with sweeping balconies overlooking the Atlantic Ocean. Your vacation hideaway is......

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  • Non Smoking

$1500 per night *
Real World MTV House---Not Just a House Your Own Private Resort

Max Guests: 16Bedrooms: 8Bathrooms: 4.5Type: HomeLocation: Key West
This isn't just a house, this is your own private mini resort in Key West, Florida. THERE IS NO OTHER PROPERTY THAT COMPARES TO THIS IN KEY WEST- 500 FEET OCEANFRONT- 6000 SQ FOOT LIVING-ACTIVITIES-SECLUDED This is the property used by MTV to fil......

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  • Pet Friendly
  • Non Smoking

$1800 - $3650 per month *
1 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
CASITA de CATHERINE - Come stay and play in this cozy cottage only steps away from Duval Street! Sunny days and tropical breezes are guaranteed at the Casita de Catherine, it’s the perfect place to relax, rejuvenate, and relish all the greatness you came to expect for your stay in the Florida Keys. This classic cottage is a one bedroom home with gorgeous décor yet still plenty of space to entertai...

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  • Pet Friendly

$270 - $480 per night *
Beach Club #104

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful tropical flare. It features a huge oceanfront balcony accessed from both the living/dining area ......

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  • Non Smoking

Hemingway Hideaway in the Heart of Key West--Tasteful, Charming

Max Guests: 4Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Historic charmer, one block from Ernest Hemingway's home, great location, and off street parking for two cars. There is historic context to Ernest Hemingway with this home. Freshly refurbished home with new furniture. The house has a great back pa......

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  • Non Smoking

Star of the Sea - Waterfront Condominium With Stunning Views!

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Luxurious! Comfortable! Unforgettable! Located on the Atlantic Ocean with magnificent views, this beautifully decorated tropical island condo offers everything you needs for a fantastic vacation. A Private Beach, Public Beaches, Tennis Courts, ......

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  • Non Smoking

$3000 - $6500 per month *
3br - Tropical Key West Vacation Home

Max Guests: 8Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Welcome to the Duncan House - your home away from home in beautiful Key West. The Duncan house is a renovated house expanded with three bedrooms and two baths located in a quiet, Old Town, Key West neighborhood only 10 minutes to Duval Street and only 5-10 minutes to Smathers Beach. 3 Bedrooms provide enough sleeping space for up to 6 people. The Master bedroom has a king bed, the 2 other bedrooms...

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  • Non Smoking

$6000 - $15000 per month *
“MAISON TROPICALE @ SOLARES HILL': Lush 3BR/3BA Old Town Home, Pool &

Max Guests: 8Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Imagine a traditional conch home in the Solares Hill section of Old Town stunningly restored, then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with uni......

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  • Non Smoking

$2610 - $4200 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed residence, custom finished with classic sophistication and appointed with every modern convenience. Walk a few blocks to fabulous dining and shopping opport...

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$5900 per week *
One of a Kind Luxury Home - Admirals Treasure

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
This is a one of a kind luxury home located in prestigious Truman Annex. We offer 4500 square feet that features 4 BR and 4BA, a 30 foot private heated pool with waterfall, dual level decks, roof top terrace and mature tropical landscaping for pr......

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  • Non Smoking

4 br Key West Condo Vacation Rental

Max Guests: 12Bedrooms: 4Bathrooms: 4Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$419 per night *
2br - Affordable Luxury in the Keys

Max Guests: 5Bedrooms: 2Bathrooms: 2.5Type: CondoLocation: Key West
Beautiful landscaped property & contemporary house will offer you a serene-tropical perfect for complete relaxation & enjoyable getaway . Situated off to azure water of Atlantic Ocean , just minutes distance from down town Key West which is known for the historic landmarks, quaint boutiques, romantic sunsets on Mallory Square , Sight seeing & dancing on Sloppy Joes . Water front condo rentals on K...

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  • Non Smoking

$2400 - $4200 per month *
1 br Key West Condo Vacation Rental

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL A spacious ground floor one bedroom in a four unit condominium building in the Casa Marina District of Key West. A great apartment for a single or couple, the unit has a reverse layout with the living room in the rear of the property off a good size back porch by the pool. The decor is soothing with no strong color, just warm tones with tropical accents throughout. The master...

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$370 - $620 per night *
3 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most photographed "Prohibition fence" in Key West, this home has a large private, sunny pool and deck, off street parking ( 1 space) , central air conditioning, and lot's of room to spread out and relax in a very convenient (but sometimes noisy) location. This home is furnishe...

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  • Pet Friendly

1 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space permitting), private off-street parking, outdoor grills, fish cleaning station, large balconies, cable TV, CD stereo system, private baths for all bedrooms w...

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  • Pet Friendly
  • Non Smoking

$4000 - $7500 per month *
Old Town Key West 2 bedroom Cottage with Private Pool

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CottageLocation: Key West
Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just four blocks from Duval Street, home of world famous watering holes, shopping and dining. Walking up Virgi......

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  • Non Smoking

$3000 - $3733 per month *
Garden Villa

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
A delightful, deluxe one bedroom condo unit in the beautiful Southard Square complex. There's a king size bed in the bedroom and a sleeper sofa in the large and elegant living room. An entertainment island separates the kitchen from the living roo......

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  • Non Smoking

$1200 - $1500 per week *
Villa Nomade, Elegant Truman Annex condo in Old Town

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Villa Nomade is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach be......

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  • Non Smoking

$300 - $488 per night *
A Zen Ocean Garden

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condominium for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxat......

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  • Non Smoking

Treetop Island Treasure, Palm Isle, Just off Duval

Max Guests: 4Bedrooms: Bathrooms: 1Type: ApartmentLocation: Key West
Palm Isle - a room ahead of its time - A truly "green unit". Your room mate or in this case "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private Jacuzzi and treetop hammock. The second-story studio "sweet" co......

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  • Non Smoking

$200 - $370 per night *
La Brisa #405E Sea Orchid

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South ......

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  • Non Smoking

$200 - $300 per night *
Pelican Landing Bonaire Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$700 - $1050 per night *
Southard Street - Queen Conch

Max Guests: 8Bedrooms: 4Bathrooms: 4Type: HomeLocation: Key West
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Down......

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  • Non Smoking

$190 - $384 per night *
Egret Cottage

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
EGRET COTTAGE -- An Idyllic 1 bedroom cottage that is tucked away in a tropical oasis, peaceful and serene yet located in one of the most ideal neighborhoods in Key West. The Colony Suites is a charming compound nestled in the heart of Historic O......

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  • Non Smoking

$429 - $449 per night *
Santa Maria Suites- Luxury Two Bedroom Suites

Max Guests: 5Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Guest suites with private balconies and terraces enclose a secret garden sanctuary. The clever attention-to-detail extends to each of our stunning two-bedroom guest suites. The kitchen amenities alone are enough to inspire your culinary flair but ......

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  • Handicap Accessible
  • Non Smoking

$1600 - $3190 per week *
2 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 3Type: CondoLocation: Key West
KEY WEST FOUND – A striking 2 bedroom, 2.5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first floor features open and airy living/dining room area, kitchen and half bath. Kitchen is well stocked for preparing a quick breakfast on y...

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$1900 - $3600 per week *
'OLD TOWN OASIS @ TRUMAN ANNEX': Spacious 2BR/2BA Oceanfront Condo + P

Max Guests: 7Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
THE LIVING AREA: The moment you step into the spacious foyer, you'll know you have entered a special place. This home has been elegantly decorated to reflect tropical living at its finest. The living area has a 50 inch Plasma TV with expanded cabl......

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  • Handicap Accessible
  • Non Smoking

$1575 - $2100 per week *
205E La Brisa

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Bright, tropical colors and tile floors provide an island ambience to this two bedroom, two bathroom ocean view condominium. The living area and master bedroom both open onto the private balcony and create a relaxing indoor/outdoor place to unwind......

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  • Non Smoking

$1200 - $2100 per week *
Paradise Found

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
7 night minimum rental. Paradise is definitely found in this Non-Smoking, first floor end unit condo only two short blocks off of "happening" Duval Street in Old Town Key West. Located in the upscale, gated community of Truman Annex, paradise is y......

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  • Non Smoking

$2940 - $5100 per week *
3br - Louisa #039;s Private Courtyard

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: HomeLocation: Key West
Tucked behind a privacy gate, this garden setting L-shaped home is a perfect escape in the heart of Old Town. Louisa's Private Courtyard centers around the contemporary designed pool and patio space to relax and enjoy Key West's year round weather. French doors from the patio enter into the combination living room and kitchen area. Skylights continue to bring the outdoors into the living space whi...

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  • Non Smoking

$200 - $300 per night *
Pelican Landing Florida Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$4000 - $6000 per month *
3 br Key West Condo Vacation Rental

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. A residential complex, La Brisa offers a neighbo...

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$150 - $200 per night *
Pelican landing Eleuthera Room

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

Tropical and Elegant Key West House

Max Guests: 8Bedrooms: 1Bathrooms: 1Type: Location: Key West
The house is the essence of Key West elegant and tropical in the same breath of sea air as the beach is only minutes away as is famous Duval Street and Key West historic sea port full of pirate history. Pets are welcome....

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  • Non Smoking

$220 - $369 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
PAPAYA PLACE pops with color! This great 2 bedroom 2 bath condominium at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you to be lost in the tropical breezes. A perfect location if you are looking for a tranquil oceanfront setting. Master bed...

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$2500 - $5000 per week *
Key West ocean view luxury 3 bedroom Truman Annex vacation condo

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This beautiful luxurious Harbor Place ocean view condo is within the prestigious Truman Annex in Old Town. Three large bedrooms with ocean views: en suite bathr......

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  • Handicap Accessible
  • Non Smoking

Rose Lane Villa's 'Villa Rosa' 1 bedroom, 1/2 block off Duval

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: VillaLocation: Key West
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa......

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  • Non Smoking

$200 - $300 per night *
Pelican Landing Curacao Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1100 - $2538 per week *
Lavender Jungle

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a larg......

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  • Non Smoking

$1500 per week *
Boli Townhouse - a Key West Luxury Rental close to everything ! ! !

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: TownhouseLocation: Key West
Boli Townhouse is located in the Truman Annex, a gated community in downtown old Key West. The Boli Townhouse is a two bedroom (a king bed in each bedroom), two full bath unit with the master suite on the second floor. The leather sleeper sofa als......

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  • Non Smoking

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back yea......

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  • Non Smoking

$250 - $410 per night *
Duval Square Retreat

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and more quiet end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers ......

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  • Non Smoking

$225 - $388 per night *
Brisa del Mar

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
BRISA DEL MAR - This two bedroom, two bath condominium is located ocean front in a gated community with a direct view of the Atlantic Ocean. Enjoy spectacular views of the sparkling blue-green waters from your private balcony while relaxing in the......

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  • Non Smoking

$270 - $480 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This is one of the most elegant and colorful 2 bedroom units in the Key West Beach Club. It features a huge oceanfront balcony accessed from both the living/dining area and master bedroom with very nice furnishings. The master bedroom has one king bed and the second bedroom has one king and o...

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  • Non Smoking

2 br Key West Home Vacation Rental

Max Guests: 6Bedrooms: 2Bathrooms: 1Type: HomeLocation: Key West
This charming 2 bedroom, 1 bathroom house is conveniently located. Just a short distance from downtown/Duval Street, restaurants and major attractions. Fully equipped kitchen, 1 king bed, 1 queen and 1 sleeper sofa. Bedding Configuration: 1 King, 1 Queen, 1 Sleeper Sofa Additional Features: * Entertainment: Cable TV * Geographic: Downtown * Kitchen: Full Kitchen, Microwave * Living: AC Wall Units,...

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  • Non Smoking

$1100 - $2320 per week *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
FINN KEY: A beautiful 2 bedroom 1 bath downstairs condominium located in the Shipyard section of Truman Annex, a gated residential community in the heart of historic Old Town Key West. This lovely home has all the comforts including flatscreen TVs and WIFI (no dishwasher). The open floor plan runs from kitchen to dining area to living room and out the French doors to your private deck where you ca...

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$1300 - $2791 per week *
Shipyard Treasure

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
*** ASK ABOUT OUR SPECIAL MONTHLY RATES AVAILABLE FOR SUMMER 2012 *** SHIPYARD TREASURE - Great Key West location, this two bedroom one bath Shipyard condo has it all. You are centrally located to all the sites and attractions of Old Town Key W......

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  • Non Smoking

Southernmost Belle a Grand home in Historic Old Town Key West

Max Guests: 10Bedrooms: 5Bathrooms: 3Type: HomeLocation: Key West
Grand historic home in historic seaport area of Old Town Key West. Tucked behind a canopy of palms & fencing this home has a unique sense of privacy situated at the very back of the sprawling tropical grounds. This home was originally built in th......

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  • Non Smoking

$4000 - $5400 per month *
Now Available March 2012 - Key West Ocean Side Luxury On Smather's Bea

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Be our guest at one of the best that 1800 Atlantic Condominiums has to offer. With a wonderful tropical setting on the Atlantic Ocean & Smathers Beach, this designer 2 BR & 2 BA condo offers unmatched luxury & refined furnishings. Offering a par......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$2610 - $4200 per month *
Suite Caroline - Twin Palms

Max Guests: 2Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
30 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage. Imagine enjoying the luxury of your elegantly detailed res......

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  • Non Smoking

$10000 - $10667 per month *
William Street House

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Located in Old Town, This home is conveniently located within walking distance to the Seaport, restaurants, and major attractions. The house has 2 bedroom 2 bath and a nice backyard with a pool. This home is cared for by a locally-based property m......

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  • Non Smoking

$2750 per week *
2br - Beachfront home private and gated beach estate

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: HomeLocation: Key West
Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished with central air conditioning. There is a spectacular rock pool with grotto and chickee hut. Pool also h...

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  • Non Smoking

$3500 - $4800 per month *
Southard Square

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: ApartmentLocation: Key West
This townhome home has a den, master bedroom with a queen bed and full bathroom on the first floor as well as a stackable washer/dryer unit. The second level has a living room, dining area, kitchen, half a bathroom and a balcony with a grill. From......

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  • Non Smoking

Truman Annex, Old Town, Key West, Private Setting with Luxury Features

Max Guests: 5Bedrooms: 2Bathrooms: 2.5Type: HomeLocation: Key West
Fully maintained and cared for, luxury features, just two blocks from Duval and Mallory Square in Old Town Key West, a two story townhome located in the Truman Annex with a private backyard. It will delight you with its charm, central location and......

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  • Non Smoking

Wisteria ~ Old Town Key West

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
Immaculate 3 BR/2BA vacation rental home on Cudjoe Key, south of MM23 Oceanside, a quick 20 minute trip into Key West. Fully furnished, tastefully decorated with thoughtful amenities beyond the typical rental property. Central air, Bahamas fans ......

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  • Non Smoking

$265 per night *
In Good Spirits

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Warm and welcoming condominium in a quiet gated waterfront community. The open floor plan overlooks the lush gardens with sliding glass doors leading to the expansive patio surrounded by lush tropical landscape with a hint of ocean view in the dis......

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  • Non Smoking

Island Oasis

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
ISLAND OASIS: Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West Hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been tran......

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  • Pet Friendly
  • Non Smoking

$250 - $410 per night *
2 br Key West Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and more quiet end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers a well- equipped kitchen, a living room that opens to a patio. Upstairs there is a master bedroom with balcony and ensuite bath and a second bedroom and bat...

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$1775 - $2100 per week *
“AZURE AFTERNOON @ OCEANSIDE MARINA': 3BR/2BA Oceanfront Condo + Pool

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: HomeLocation: Key West
YOUR SPACIOUS OCEANFRONT BALCONY will be a front row seat for a panorama of azure blue ocean and sky. With direct views of the ocean from the living room, master bedroom and your own private balcony, you will never want to leave this quiet and pea......

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  • Pet Friendly
  • Non Smoking

$310 - $490 per night *
Duval Square Courtyard Condo

Max Guests: 6Bedrooms: 3Bathrooms: 2Type: CondoLocation: Key West
In the heart of Old Town, convenient to everything. The condo is set above a brick, tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone walkup buildings in the Duval Square comple......

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  • Non Smoking

$2200 - $4500 per month *
Carpe Diem- a tropical Conch Cottage in old town Key West -

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CottageLocation: Key West
From the owners of the award winning CARPE DIEM Spa Resort in Provincetown / MA, this quintessential Conch Cottage is close to all attractions and only a few blocks from Higgs Beach. Around the corner you’ll find the best Cuban coffee, an excelle......

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  • Pet Friendly
  • Non Smoking

$165 - $195 per night *
Quiet, elegant, Key West Condo close to the Ocean

Max Guests: 6Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Mus......

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  • Pet Friendly
  • Handicap Accessible
  • Non Smoking

$190 - $380 per night *
2 br Key West Ocean View Condo Vacation Rental

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or barbeque in the shade of this beautiful garden. When you are done relaxing by the pool,...

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$200 - $300 per night *
Pelican Landing Antigua Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$1200 - $1500 per week *
Villa Soleil, Elegant Truman Annex condo in Old Town Key West

Max Guests: 4Bedrooms: 2Bathrooms: 1Type: CondoLocation: Key West
Villa Soleil is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach be......

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  • Non Smoking

$225 - $275 per night *
Coral Hammock 36

Max Guests: 6Bedrooms: 3Bathrooms: 3Type: CondoLocation: Key West
Coral Hammock is one of the newest gated communities with 55 luxury resort homes with a lavish Clubhouse, Pool and lushly landscaped grounds. These custom single family homes recall the romantic charm of old Key West with spacious floor plans, vau......

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  • Non Smoking

$3000 - $5000 per month *
'LA PROVENCE @ THE SANCTUARY': 2 Master Suites, Spa Pool with Walled Y

Max Guests: 6Bedrooms: 2Bathrooms: 3Type: HomeLocation: Key West
'La Provence' is a bright and airy private home located in The Sanctuary, a quiet gated enclave set within the already gated grounds of the Key West Golf Club. The setting is idyllic, with lanes free of parked cars and no traffic on this peaceful ......

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  • Pet Friendly
  • Non Smoking

$190 - $384 per night *
1 br Key West Home Vacation Rental

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: HomeLocation: Key West
EGRET COTTAGE -- An Idyllic 1 bedroom cottage that is tucked away in a tropical oasis, peaceful and serene yet located in one of the most ideal neighborhoods in Key West. The Colony Suites is a charming compound nestled in the heart of Historic Old Town Key West, just three blocks from famous Duval Street with its incredible art galleries, boutiques, museums, attractions, restaurants, and nightclu...

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$200 - $300 per night *
Pelican Landing Dominica Suite

Max Guests: 4Bedrooms: 1Bathrooms: 1Type: CondoLocation: Key West
Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy your stay at Pelican Landing. Our secure building has elevators, full-size heated pool, free boat slip (space perm......

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  • Pet Friendly
  • Non Smoking

$410 - $700 per night *
Duval Roost

Max Guests: 6Bedrooms: 3Bathrooms: 3.5Type: HomeLocation: Key West
This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the property through a secure privacy fence into the pool courtyard area. The large house towers above with high ceilings an......

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  • Non Smoking

$180 - $370 per night *
La Brisa #403E Ocean Vista

Max Guests: 4Bedrooms: 2Bathrooms: 2Type: CondoLocation: Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roo......

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  • Non Smoking
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*Final rates are based on travel dates, taxes, insurance and other factors.