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Key West House Rentals

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    $449
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    1 / 11
    4.5 of 5 stars (38) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 / 8
    4.5 of 5 stars (49) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    1 / 17
    4 of 5 stars (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 / 18
    4 of 5 stars (40) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    About this property
    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... View all property information
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    Key West, Florida Keys 33040
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    $7,575
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    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    HELICONIA HOUSE (monthly rental): Pristine 3 bedroom private home is a true island escape.Located in a quiet Old Town residential neighborhood. Only two short blocks to Duval Street . An open living room and dining room to dine or relax. Luxurious king bed with bath ensuite. Glass doors open... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $9,178
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    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2
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    • x
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    About this property
    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... View all property information
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    Key West, Florida Keys 33040
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    $13,567
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $16,759
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    1 / 17
    4 of 5 stars (2) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Satellite TV
    • Private Outdoor...
    • Stereo System
    • DVD Player
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    • Deck
    • Patio
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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
    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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $519
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    1 / 19
    4 of 5 stars (42) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Internet Access
    • Satellite TV
    • Deck
    • Air Conditioning
    • Private Outdoor...
    • Stereo System
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed 'prohibition fence' in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $194
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    1 / 10
    Studio, 1 Bathroom, Sleeps 2
    Overview Make Enquiry
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    • Shared Outdoor Pool...
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    • Linens Provided
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    • x
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    About this property
    It is a pleasure to present the recently renovated Room Nine! It used to be a good room, now it's a great room! Comfortable and very peaceful, this room was originally opened up to make use of a portion of the attic space. Note that the ceiling is sloped in two directions and some taller guests... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    From
    $337
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    1 / 16
    4.5 of 5 stars (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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    • DVD Player
    • Air Conditioning
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    About this property
    This charming one bedroom cottage is the perfect hideaway. 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. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $309
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    1 / 14
    4.5 of 5 stars (45) Very good
    Studio, 1 Bathroom, Sleeps 2
    Overview Reviews (45) Make Enquiry
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    • Refrigerator
    • Shared Outdoor Pool...
    • Satellite TV
    • Stereo System
    • Patio
    • DVD Player
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
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    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. 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. Within 2 blocks you'll find Key West... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,052
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    1 / 23
    5 of 5 stars (28) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Grill
    • DVD Player
    • Deck
    • Stereo System
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,515
    / Night
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    1 / 24
    5 of 5 stars (20) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Hot Tub
    • Deck
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $652
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    1 / 26
    4.5 of 5 stars (79) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (79) Make Enquiry
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    • Private Outdoor...
    • Grill
    • Air Conditioning
    • Internet Access
    • TV
    • DVD Player
    • Hairdryer
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    BAHAMA DREAMING: 3-bedroom Conch cottage with outdoor dining and private pool, fenced and landscaped, off-street parking, 1/2 block from Duval Street. Downstairs has 2 bedrooms (queen and 2 twins), living room with sleeper sofa and full bathroom, kitchen and covered back porch. A couple steps... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $14,047
    / Month
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    1 / 13
    3.5 of 5 stars (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Satellite TV
    • Patio
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Stereo System
    • Internet Access
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $379
    / Night
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    1 / 13
    4 of 5 stars (43) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (43) Make Enquiry
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    • Grill
    • Private Outdoor...
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $379
    / Night
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    1 / 13
    2.5 of 5 stars (2) Poor
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Internet Access
    • Shared Outdoor Pool...
    • Stereo System
    • Refrigerator
    • Patio
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Key West, Florida Keys
    From
    $617
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 2
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    • Balcony
    • Satellite TV
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    • Internet Access
    • Stereo System
    • Refrigerator
    • Patio
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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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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    Location Information
    Key West, Florida Keys
    From
    $4,489
    / Month
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    1 / 28
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Parking
    • Grill
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    • Air Conditioning
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    ISLAND BREEZE: Located in the exclusive Sanctuary within the Key West Golf Club, this is a spacious home with 3 bedrooms and a sleeper sofa. Enter an open floor plan of kitchen, dining room, half-bath and living room, with French doors leading outside to the private deck. Upstairs offers the... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    From
    $19,154
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    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
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    • Internet Access
    • Deck
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    • Grill
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    30 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical... View all property information
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    Location Information
    Key West, Florida Keys
    From
    $11,652
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Air Conditioning
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    • Hot Tub
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    • Private Outdoor...
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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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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    Key West, Florida Keys 33040
    From
    $757
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Internet Access
    • DVD Player
    • Deck
    • Patio
    • Private Outdoor...
    • Stereo System
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Key West, Florida Keys 33040
    From
    $379
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    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
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    • Patio
    • Refrigerator
    • Internet Access
    • Stereo System
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys
    From
    $2,946
    / Month
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    1 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 4
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    • Grill
    • TV
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    • Balcony
    • DVD Player
    • Terrace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo. It's not Bermuda or the Bahamas but better, a... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $659
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    1 / 28
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
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    • DVD Player
    • Deck
    • Satellite TV
    • Refrigerator
    • Stereo System
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys
    From
    $11,652
    / Month
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Linens Provided
    • Deck
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    • Dishwasher
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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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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    Location Information
    Key West, Florida Keys
    From
    $814
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    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Internet Access
    • Satellite TV
    • Deck
    • Private Outdoor...
    • Stereo System
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined... View all property information
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    Location Information
    Key West, Florida Keys
    From
    $278
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    1 / 30
    4.5 of 5 stars (30) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
    other travellers have booked this property
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    • Patio
    • Deck
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    • Satellite TV
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    • 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
    $3,086
    / Month
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    1 / 28
    1 Bedroom, 2 Bathrooms, Sleeps 2
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    Overview
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    • Air Conditioning
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Grill
    • Hairdryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • ?
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    About this property
    COCONUT COTTAGE: The perfect escape if you’re looking to get away from it all. Located in a quiet neighborhood of Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest your head in our island city. Enter the property in a cozy sitting room. The living room and kitchen are... View all property information
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    Key West, Florida Keys 33040
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    $306
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    4 of 5 stars (38) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • Deck
    • Patio
    • Satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
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    Key West, Florida Keys 33040
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    $250
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    4.5 of 5 stars (19) Very good
    Studio, 1 Bathroom, Sleeps 2
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    • Grill
    • Air Conditioning
    • Internet Access
    • Refrigerator
    • Deck
    • Hot Tub
    • Patio
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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    Key West, Florida Keys 33040
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    $264
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    4.5 of 5 stars (22) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • 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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    Key West, Florida Keys 33040
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    $302
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    1 / 24
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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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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    $2,665
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    1 / 24
    4 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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    • TV
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
    • Hairdryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    IBIS - 1 bedroom 1 bath condo 2 blocks from Duval Street, part of The Colony compound.Simple but comfortable, kitchenette opens onto the living area with a flat screen TV. The bedroom has a queen bed with TV and bath ensuite.WIFI, flatscreen TV, community coin-op laundry and swimming poolQ/Qslpr... View all property information
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    Key West, Florida Keys 33040
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    $1,105
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    4 of 5 stars (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12
    other travellers have booked this property
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    • Parking
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • 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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    Key West, Florida Keys 33040
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    $572
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    1 / 36
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Ceiling Fans
    • Hairdryer
    • Air Conditioning
    • Parking
    • Internet Access
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    • 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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    Key West, Florida Keys 33040
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    $302
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    4.5 of 5 stars (44) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Deck
    • Washer
    • Shared Outdoor Pool...
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Key West, Florida Keys 33040
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    $6,873
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    1 / 24
    4.5 of 5 stars (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Internet Access
    • Deck
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Key West, Florida Keys 33040
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    $2,946
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
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    • Terrace
    • DVD Player
    • Shared Outdoor Pool...
    • Balcony
    • TV
    • Internet Access
    • Hairdryer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A LITTLE SLICE OF PARADISE (monthly rental): Secluded community, steps from the golf course, minutes from the beach, airport and some of the locals' favorite restaurants. 2 bedrooms, 1 full bath upstairs; open floor plan downstairs with sleeper sofa for guests, half bath, and screened porch.... View all property information
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    Key West, Florida Keys 33040
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    $982
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    4.5 of 5 stars (11) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10
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    • DVD Player
    • Stereo System
    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    • Wi-Fi
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • 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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    Key West, Florida Keys 33040
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    $561
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    1 / 24
    5 of 5 stars (20) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Stereo System
    • Washer
    • Air Conditioning
    • Deck
    • Satellite TV
    • DVD Player
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Key West, Florida Keys 33040
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    $561
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    1 / 25
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Air Conditioning
    • Washer
    • Internet Access
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    • Deck
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the... View all property information
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    Key West, Florida Keys 33040
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    $351
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    4 of 5 stars (35) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Internet Access
    • Elevator/Lift access
    • Satellite TV
    • Hot Tub
    • Deck
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Key West, Florida Keys 33040
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    $2,946
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    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hairdryer
    • Terrace
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool...
    • Internet Access
    • TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    WIND SWEPT: 2 bedroom 1.5 bath townhome which includes kitchen, dining alcove, living room and screened-in sitting room. A few doors away from the community pool and clubhouse makes this the perfect location for a month (or two) of peace and serenity at Key West Golf Club.Upstairs you will find... View all property information
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    Key West, Florida Keys 33040
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    $376
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    4.5 of 5 stars (48) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travellers have booked this property
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    • Hot Tub
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Deck
    Suitability
    • 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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    $842
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    5 of 5 stars (12) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Washer
    • Satellite TV
    • Deck
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Wi-Fi
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Key West, Florida Keys 33040
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    $386
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    4.5 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Shared Outdoor Pool...
    • Deck
    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Key West, Florida Keys 33040
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    $572
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    4.5 of 5 stars (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travellers have booked this property
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    • 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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    Key West, Florida Keys 33040
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    $3,787
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    2 Bedrooms, 3 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
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    • Hairdryer
    • Air Conditioning
    • TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    GREEN ORCHID: Situated on a narrow lane in one of the last historic Old Town neighborhood, this 2-bedroom 2.5 bath home has it all!Living room has French doors opening to let in the tropical breezes. Modern, stainless kitchen. Outdoor shower on the lushly landscaped walkway. Guest bedroom with... View all property information
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    Key West, Florida Keys 33040