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House Rentals and Apartments in Key West, FL

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    $270
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines 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... View all property information
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    1 / 14
    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    About this property
    SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living... View all property information
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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... View all property information
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    30 DAY MINIMUM RENTAL Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite Flaming Buoy restaurant.... View all property information
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    1 / 21
    1 Bedroom / 2 Bathrooms / Sleeps 2
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    About this property
    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    30 DAY MINIMUM RENTAL 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,... View all property information
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    1 / 23
    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Two bedrooms, two and a half baths, Foundry Condo 121 Front Street in the Truman Annex, is located in the heart of Key West's Old Town. Fly in and take a taxi from the Key West airport or the Keys Shuttle from the Miami or Ft. Lauderdale airports. One reserved vehicle parking space. Available for... View all property information
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    1 / 32
    4.5 of 5 stars (5) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
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    • Sauna
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    About this property
    Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. 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 discover the charm and grace of Old Key... View all property information
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    1 / 38
    5 of 5 stars (34) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
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    1 / 30
    5 of 5 stars (36) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Water Views
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
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    4.5 of 5 stars (20) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was... View all property information
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation... View all property information
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    1 / 19
    4 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Pets allowed
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    • Suitable for children
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    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse... View all property information
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    1 / 24
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Washer
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    • Pets allowed
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    • Suitable for children
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    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just... View all property information
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    1 / 24
    4.5 of 5 stars (25) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Air Conditioning
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    • Pets allowed
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    About this property
    This gracious one bedroom, one bath conch cottage with private pool is the perfect place for your dream vacation. Casablanca is set back from White Street which runs the fourteen-block width of the island from the Gulf of Mexico to a fishing pier jutting out into the wide Atlantic Ocean. The... View all property information
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    $198
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    1 / 29
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    • Air Conditioning
    • Balcony
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    • Wi-Fi
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    • Pets allowed
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    About this property
    La Dolce Vita is the sister unit to the Bella Vita in the same building, Flip Key listing #333914. Steps from Duval Street! 'La Dolce Vita' is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to... View all property information
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    1 / 37
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
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    About this property
    A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic Key West, you will be only 4 blocks from world famous Duval Street and 3 blocks away from the scenic Historic Seaport of Key West. Please see our video!! When you arrive, park your car in your... View all property information
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    1 / 24
    4.5 of 5 stars (15) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
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    1 / 25
    4.5 of 5 stars (15) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Washer
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    • Pets allowed
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    About this property
    Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs, and shade... View all property information
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    1 / 25
    4.5 of 5 stars (20) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
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    1 / 22
    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
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    1 / 14
    4.5 of 5 stars (16) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    This weekly (minimum) condo is in a perfect location for enjoying all the sights of Old Town Key West - a car is not even necessary as you can walk to everything! Fly in to Key West or take the Keys Shuttle from the Miami or Ft. Lauderdale airports. This rare condominium with a second full bath... View all property information
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    1 / 22
    4.5 of 5 stars (70) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way,... View all property information
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    1 / 25
    4.5 of 5 stars (21) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Dryer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket... View all property information
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    1 / 24
    4.5 of 5 stars (25) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Everybody knows it's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and... View all property information
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    1 / 25
    4.5 of 5 stars (42) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Pets allowed
    • Smoking allowed
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens... View all property information
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    1 / 8
    Studio / 1 Bathroom / Sleeps 2
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    • Waterfront
    • Water Views
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    About this property
    Want to have a piece of Paradise to call your own? Even tho it for a short stay?…Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! We are So glad you found us! The Best Stay In Key West! {{{ 5nt Here! $1550 includes tax & cleaning! call if for your date... View all property information
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    1 / 25
    4.5 of 5 stars (11) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other... View all property information
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    1 / 25
    4.5 of 5 stars (38) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
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    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
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    4 of 5 stars (35) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
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    About this property
    The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best... View all property information
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    5 of 5 stars (9) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort... View all property information
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    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Balcony
    • Grill
    • Ocean Views
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    See if this unit is for you! Want to have a piece of Paradise to call your own? Even tho it for a short stay?… read rates then call- NO QUOTES BY EMAIL thank you Questions by phone! Give a call Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! We are So... View all property information
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the... View all property information
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    5 of 5 stars (10) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,... View all property information
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    4.5 of 5 stars (11) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... View all property information
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    5 of 5 stars (2) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
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    5 of 5 stars (8) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveler have booked this property
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    • Air Conditioning
    • Balcony
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    The Bella Vita is a 1 Bedroom, 1 bath, luxurious, steps from Duval Street. Bella Vita is the sister unit to the La Dolce Vita in the same building, listing 431504. Please check out our for availability, photos and video. Everything is brand new from floor ceilings! 14... View all property information
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    5 of 5 stars (18) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around... View all property information
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    5 of 5 stars (49) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special... View all property information
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    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    MONTHLY RENTAL ONLY Fantastic 2nd floor studio with a large private deck located just one block from famous duval street. This tree top studio is cozy. For your convenience there is a kitchennette with a 2 burner stove, microwave oven and a toaster oven. There is a brand new queen size sleeper sofa... View all property information
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    5 of 5 stars (9) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is on the... View all property information
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    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 studios within a block, coffee shops, and a grocery... View all property information
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • ?
    • x
    About this property
    Great 3rd floor 2 bedroom 2 bath rental unit at 1800 Atlantic. All furnishings replaced in 2011,decorated in an elegant contemporary style. This unit is spacious with a full size fully equipped eat in Kitchen. There is a king bed in the master bedroom, 2 twin beds in the 2nd bedroom and a queen... View all property information
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    $350
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both Bedrooms and the living room open onto the expansive private... View all property information
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    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story 'cottage' offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living... View all property information
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