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House Rentals in Key West, FL

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    Travellers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 31
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 24
    4.5 of 5 stars (27) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 16
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Live in the lap of luxury in this stunningly renovated Key West classic 'Eyebrow House.' An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this... View all property information
    Location Information
    Key West, Florida Keys
    1 / 30
    4 of 5 stars (39) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect 'get away' spot for individuals looking to fully immerse themselves in Key West culture. This house is... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4 of 5 stars (5) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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
    1 / 38
    5 of 5 stars (36) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • x
    • x
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $2,645
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    • DVD Player
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    • Porch
    • Secure Parking
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    • Pet-friendly
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    • ?
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    • Elder access
    • x
    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 stars (34) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 29
    4 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • Terrace
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    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
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $4,873
    / Week
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    • Grill
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    • ?
    • x
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    • x
    About this property
    OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $251
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    • Terrace
    • Internet Access
    • Washer
    • Parking
    • Air Conditioning
    • DVD Player
    • Balcony
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start your day of... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 stars (42) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $2,088
    / Week
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    • DVD Player
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    • Balcony
    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony on the 2nd floor deck. In case you would like to work on vacation the unit has a wireless DSL connection. There is one assigned parking space per unit.... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $7,657
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    • Elder access
    • x
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    About this property
    ***BRAND NEW POOL COMPLETED SEPTEMBER 2015*** Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    3 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $401
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    About this property
    Part of TROPICAL VILLAGE Southern Cross: Lounging next to the gorgeous shared pool or sitting 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 the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $313
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    • Parking
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    • Patio
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is 'Key West' from scenes around the area including... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $1,009
    / Week
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    • Internet Access
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Beautiful second floor studio for two on the second floor of the historic Sailmaker's House. - Incredible location in Historic Old Town! This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. The open floor plan maximizes the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
    From
    $8,353
    / Month
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    • Internet Access
    • Waterfront
    • Patio
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    • Grill
    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.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the... View all property information
    Location Information
    Key West, Florida Keys
    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    From
    $390
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    • Balcony
    • Satellite TV
    • Patio
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
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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
    Location Information
    Key West, Florida Keys
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    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $4,873
    / Week
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
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    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living environment - (1) full bed, (1) queen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 stars (54) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $348
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    • Shared Outdoor Pool...
    • Balcony
    • DVD Player
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    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $4,733
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    • Patio
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    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 stars (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $373
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (58) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • DVD Player
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $2,123
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    'South Street Serenity' This light and airy 3 bedroom, 2.5 bath home has a wrap around deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private gate and you will be in a tropical paradise, surrounded by lush palms, fiery bougainvillea, and... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4 of 5 stars (4) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    $248
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value. This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,... View all property information
    Location Information
    Key West, Florida Keys
    1 / 28
    4 of 5 stars (14) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    • ?
    • ?
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    • x
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    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 unit... View all property information
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    Key West, Florida Keys
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $1,062
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    • Grill
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    • x
    • ?
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    • x
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    About this property
    Banana Dream offers you exceptional value and an opportunity to enjoy Key West at its best! This is a charming 2 bedroom / 2 bath - first floor condominium. It is furnished with all of the comforts you would expect from a vacation home in paradise. Enjoy a frozen beverage while sitting in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $4,177
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Hemingway's Shadow is a well-appointed, 1 bedroom home located on Thomas Street, directly behind the Key West Lighthouse Museum. The living room, dining area and kitchen form an L-shape open area. The kitchen... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $3,480
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • ?
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    • Elder access
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    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic home. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front entrance with sweeping front porch over Caroline Street- this... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 stars (8) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
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    Key West, Florida Keys
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (21) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 stars (20) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***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 a... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Open the front door of the hand crafted Havana Moon Key West cottage located on Upper Duval Street, step from the porch, and look south toward Havana Cuba and... Mmmm... You'll catch a view of the ocean where the full moon rises with a soft salt southern breeze. Originally built in the late 1800's... View all property information
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    Key West, Florida Keys 33040
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Havana Oasis is comprised of two of our most popular homes! Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey.... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly... View all property information
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    Key West, Florida Keys
    1 / 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    . Additional amenities include: upstairs unit, close to pool, washer/dryer, stereo/cd/radio. View all property information
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    Key West, Florida Keys
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    Minimum 90 day stay requirement- Las Salinas is well maintained and has a beautiful community pool. Offers covered parking. There is a shared swimming pool.Located in New Town featuring 1 bedroom with a queen sized bed and one bathroom. The unit has a private balcony and offers covered parking.... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Recently updated with new furnishings, premium linens, wifi and flat screen TV Feeling the need for an antidote to mainland stress? Or maybe you’ve finally decided to write that novel, paint that picture or write that piece of music that’s been tickling your brain? Solaris Cottage, located on... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $258
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    Hello,and welcome! This is cool and comfortable room with private bathroom, it comfortably fits two and it is located on a quiet street just 10 min away from Duval by car The apartment is very clean, complete renovation was done a month ago, everything is new and cool Room: Adorable bedroom,... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4 of 5 stars (37) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 a... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,... View all property information
    Location Information
    Key West, Florida Keys 33040