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Houses in Key West, FL

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    All 558 Rentals in Key West
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    From
    $455
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    1 / 25
    5 of 5 stars (40) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (40) Make Enquiry
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    $372
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    1 / 25
    4.5 of 5 stars (22) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    $358
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    1 / 24
    4.5 of 5 stars (25) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    Welcome, see what other travellers are looking for in Key West
    Water views
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    $280
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    1 / 25
    4.5 of 5 stars (11) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Stereo System
    • Dryer
    • Refrigerator
    • DVD Player
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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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    Key West, Florida Keys 33040
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    $390
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    1 / 12
    4 of 5 stars (14) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (14) Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Dishwasher
    • Internet Access
    • Linens Provided
    • Balcony
    • Gym
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    Key West, Florida Keys 33040
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    1 / 24
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
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    • Parking
    • Grill
    • Satellite TV
    • Stereo System
    • DVD Player
    • Hot Tub
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled midway between the Atlantic Ocean and the Gulf of Mexico is Casa Alegre, an easy-living one-bedroom, one-bath duplex cottage featuring a bubbling hot tub on its own private deck. The White Street corridor is an Old Town neighborhood unto itself, yet the world-famous Duval Street in easy... View all property information
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    Key West, Florida Keys 33040
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    $967
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    1 / 22
    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    Amenities & Details
    • Stereo System
    • DVD Player
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • 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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    Key West, Florida Keys 33040
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    $336
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    1 / 23
    4.5 of 5 stars (18) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Deck
    • Shared Outdoor Pool...
    • Refrigerator
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Linens Provided
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town.... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $219
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    1 / 21
    4.5 of 5 stars (24) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (24) Make Enquiry
    Amenities & Details
    • Terrace
    • Grill
    • Linens Provided
    • Air Conditioning
    • Satellite TV
    • Refrigerator
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $6,050
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    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • TV
    • Parking
    • Grill
    • Internet Access
    • Hairdryer
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $180
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    1 / 27
    5 of 5 stars (2) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $531
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    1 / 24
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of TROPICAL VILLAGE Toon Hall: 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 home has two... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $245
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    1 / 26
    4.5 of 5 stars (48) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (48) Make Enquiry
    Amenities & Details
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $323
    / Night
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    1 / 29
    4 of 5 stars (9) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • Air Conditioning
    • Refrigerator
    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $390
    / Night
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    1 / 23
    4.5 of 5 stars (26) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (26) Make Enquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Balcony
    • Linens Provided
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $492
    / Night
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    1 / 37
    4.5 of 5 stars (11) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Refrigerator
    • Grill
    • Deck
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $531
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    1 / 33
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Internet Access
    • Hairdryer
    • Air Conditioning
    • Ceiling Fans
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of Southern Palms COCONUT PALM (formerly 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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $206
    / Night
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    1 / 24
    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of TROPICAL VILLAGE Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $258
    / Night
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    1 / 30
    4.5 of 5 stars (30) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
    traveller have booked this property
    Overview Reviews (30) Make Enquiry
    Amenities & Details
    • Patio
    • Deck
    • Shared Outdoor Pool...
    • Satellite TV
    • Refrigerator
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with a... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $7,155
    / Week
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    1 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Grill
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • TV
    • Internet Access
    • Hairdryer
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a prestigious gated community in Old Town. Surrounded by tropical greenery in a beautiful quiet gated community 2 blocks from Duval Street and... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $219
    / Night
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    1 / 28
    4 of 5 stars (26) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (26) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Balcony
    • Deck
    • Internet Access
    • Air Conditioning
    • Grill
    • Linens Provided
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $5,854
    / Month
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    1 / 22
    4.5 of 5 stars (19) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (19) Make Enquiry
    Amenities & Details
    • Refrigerator
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    • Deck
    • Grill
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The master bedroom decorated in Key West styled décor has a queen-size bed and full bathroom with tub. The second bedroom has 2 twin-size beds that can also be converted in to a king upon request. The fully... View all property information
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    Key West, Florida Keys 33040
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    $531
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    1 / 26
    4.5 of 5 stars (10) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • Refrigerator
    • Patio
    • Air Conditioning
    • Grill
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $245
    / Night
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    1 / 28
    4.5 of 5 stars (22) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • DVD Player
    • Internet Access
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $492
    / Night
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    1 / 29
    5 of 5 stars (13) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • Grill
    • Patio
    • Satellite TV
    • Deck
    • Internet Access
    • Refrigerator
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,025
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    1 / 24
    4 of 5 stars (1) Very good
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located at 729 Whitehead St, 'Southern Palms' is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $3,252
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    1 / 11
    4 of 5 stars (6) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Gym
    • Private Outdoor...
    • Patio
    • Deck
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This cottage features a cozy master suite which encompasses the entire 2nd floor. This bedroom features a pillow top King bed, large flat screen TV, en-suite bath with shower. The living room has a queen... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $245
    / Night
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    1 / 22
    4 of 5 stars (13) Very good
    Studio / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Balcony
    • Deck
    • Refrigerator
    • Internet Access
    • Grill
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located at Papa's Hideaway Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling through the palms, blowing each of your cares away... This Deluxe Studio is located on the ground floor and offers a private porch just off of the pool area. The... View all property information
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    Location Information
    Key West, Florida Keys
    From
    $375
    / Night
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    1 / 32
    3 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of TROPICAL VILLAGE Southern Cross: 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 vacation cottage is surrounded by exotic gardens, and situated in... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $4,163
    / Month
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    1 / 26
    5 of 5 stars (1) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • TV
    • Terrace
    • Grill
    • Internet Access
    • Parking
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    CAYO HUESO SUNSHINE: 2-bedroom, den, 3-bath home. Secluded location near Smathers Beach. Kitchen island countertop is a perfect spot for casual meals. Glass doors open to a private yard, outside dining and your own pool. Upstairs bedrooms feature king size beds with en suite baths.Downstairs... View all property information
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    Key West, Florida Keys 33040
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    3.5 of 5 stars (3) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Grill
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    • Refrigerator
    • Satellite TV
    • Patio
    • Air Conditioning
    • Deck
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** This recently renovated two bedroom/two bathroom vacation dream home offers an open floor plan with the best of appointments throughout including hardwood floors, marble counter tops and impeccable style.... View all property information
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    Key West, Florida Keys
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    $193
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    4.5 of 5 stars (24) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Internet Access
    • Deck
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    Key West, Florida Keys 33040
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    4 of 5 stars (5) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Internet Access
    • Grill
    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
    • Deck
    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million... View all property information
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    Key West, Florida Keys 33040
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    $336
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    1 Bedroom / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Linens Provided
    • Satellite TV
    • Microwave
    • Refrigerator
    • Internet Access
    • Terrace
    • Balcony
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • x
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    About this property
    Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic 'Cuban Club' on the 'quieter' side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
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    Key West, Florida Keys 33040
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    $390
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    4.5 of 5 stars (26) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • DVD Player
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Linens Provided
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
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    $336
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    4.5 of 5 stars (15) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Deck
    • Internet Access
    • DVD Player
    • Hot Tub
    • Grill
    • Satellite TV
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features... View all property information
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    Key West, Florida Keys 33040
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    $349
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    4.5 of 5 stars (24) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Deck
    • Balcony
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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    Key West, Florida Keys 33040
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    $349
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    4.5 of 5 stars (47) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Hot Tub
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Deck
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Inside, you will find all of the comforts of home and This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor.... View all property information
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    Key West, Florida Keys 33040
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    $180
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    4.5 of 5 stars (30) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Internet Access
    • Satellite TV
    • Grill
    • Air Conditioning
    • Linens Provided
    • Patio
    • Microwave
    • Refrigerator
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • x
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    About this property
    The Mallory Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    Key West, Florida Keys 33040
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    $5,204
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • DVD Player
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Balcony
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    EASY LIVIN' : Private home with pool in Truman Annex, a gated community in historic Old Town, in walking distance of anything you'll want to do during your visit.Bricked yard with outdoor living space and tranquil pool; custom built by the owners with family gatherings in mind. 3 bedrooms,... View all property information
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    Key West, Florida Keys 33040
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    $245
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    4.5 of 5 stars (30) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Deck
    • Refrigerator
    • Shared Outdoor Pool...
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a w/ Queen Sleeper Sofa. Efficiency kitchen is fully equipped for cooking w/... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (36) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Internet Access
    • Deck
    • Patio
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Romantic Retreat features a king pillow-top bed, Tommy Bahama furniture, flat screen TV and tropically inspired original fine art. The recently renovated kitchen includes granite counter tops, under counter refrigerator, microwave, toaster/oven, coffee maker, blender and soft mood lighting under... View all property information
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    Key West, Florida Keys 33040
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    $271
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    4.5 of 5 stars (24) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Linens Provided
    • Satellite TV
    • Deck
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
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    Key West, Florida Keys 33040
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    $284
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    1 / 27
    4 of 5 stars (23) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • DVD Player
    • Internet Access
    • Satellite TV
    • Refrigerator
    • Grill
    • Air Conditioning
    • Deck
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while... View all property information
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    Key West, Florida Keys 33040
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    $3,252
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Balcony
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • TV
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    SEASIDE ESCAPE (monthly rental): Open living space with living room, dining area and kitchen.Master bedroom with king bed and bathroom ensuite; guest bedroom has twin beds that convert to a king. Two Tempurpedic rollaways allow accommodations for the occasional guests. 1800 Atlantic offers all... View all property information
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    Key West, Florida Keys 33040
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    $544
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    4.5 of 5 stars (50) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    travellers have booked this property
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    • Refrigerator
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Deck
    • Private Outdoor...
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
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    Key West, Florida Keys 33040
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    $336
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    4.5 of 5 stars (7) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Satellite TV
    • Deck
    • Refrigerator
    • Grill
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side... View all property information
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    Key West, Florida Keys 33040
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    $5,854
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Refrigerator
    • Grill
    • Private Outdoor...
    • Patio
    • Linens Provided
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including... View all property information
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    Key West, Florida Keys 33040
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    $5,204
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    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Internet Access
    • Patio
    • Refrigerator
    • Satellite TV
    • Air Conditioning
    • Grill
    • Balcony
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The master bedroom features a king-size bed, flat screen television, en suite bathroom and french doors leading you out to the private side deck. The second bedroom features a queen-size bed and flat screen... View all property information
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    Key West, Florida Keys
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    $390
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    4.5 of 5 stars (37) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    • Balcony
    • Stereo System
    • Air Conditioning
    • Patio
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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 restaurants in the complex. Families are... View all property information
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    Key West, Florida Keys 33040