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Apartments in Key West, FL

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    $1,965
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    1 / 14
    4.5 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (12) Make Enquiry
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    1 / 10
    4 of 5 stars (55) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (55) Make Enquiry
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    $327
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    1 / 13
    4.5 of 5 stars (54) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    1 / 20
    4.5 of 5 stars (18) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (18) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    $1,618
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    1 / 25
    4 of 5 stars (2) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
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    • Balcony
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • ?
    • ?
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    • Elder access
    • ?
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    About this property
    SIESTA BAY: 2 bedroom 1 bath upstairs condo in Truman Annex, steps away from the shared pool and walking distance of anything you'd want to do in Key West. Fully equipped with everything you need to prepare meals and a dinette with seating for 4. The living room is inviting with glass doors... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $393
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    1 / 10
    4.5 of 5 stars (34) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (34) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $393
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    1 / 21
    4.5 of 5 stars (28) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (28) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    $393
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    1 / 20
    4 of 5 stars (31) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (31) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    $2,292
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    1 / 17
    4 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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. Bright, tropical colors and tile floors provide an island ambience to... View all property information
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    Key West, Florida Keys 33040
    From
    $288
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    1 / 30
    4.5 of 5 stars (10) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (10) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport.Fully equipped kitchen, HDTVs, WIFI and off-street parking... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    From
    $393
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    1 / 15
    4.5 of 5 stars (26) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (26) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $393
    / Night
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    1 / 19
    4 of 5 stars (20) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (20) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $524
    / Night
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    1 / 18
    4.5 of 5 stars (32) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (32) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $393
    / Night
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    1 / 23
    4.5 of 5 stars (24) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (24) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $360
    / Night
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling,... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $327
    / Night
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    1 / 12
    4.5 of 5 stars (60) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (60) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    Location Information
    Key West, Florida Keys 33040
    From
    $393
    / Night
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    1 / 15
    4.5 of 5 stars (22) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $393
    / Night
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    1 / 19
    4 of 5 stars (25) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (25) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    From
    $7,204
    / Month
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $4,192
    / Month
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    1 / 28
    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    $6,550
    / Month
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    1 / 31
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $589
    / Night
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    1 / 15
    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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    Key West, Florida Keys 33040
    From
    $229
    / Night
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    1 / 10
    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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    Key West, Florida Keys 33040
    From
    $7,038
    / Month
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    $3,668
    / Month
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    1 / 22
    5 of 5 stars (4) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    SUNSET LAKE -- Discover paradise and empty yourself of worries & hurries. Set at the end of a quiet lane, amid tropical landscaping, this 3-bedroom 3-bath townhome exudes an ambiance of peace and tranquility. The spacious interior overlooks the 15th and 17th holes on the Rees Jones designed golf... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $4,323
    / Month
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    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    Location Information
    Key West, Florida Keys 33040
    From
    $337
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered deck for your... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,048
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    1 / 21
    4.5 of 5 stars (4) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $426
    / Night
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    1 / 8
    4 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $3,406
    / Month
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    1 / 24
    3.5 of 5 stars (7) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Hot Tub
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $884
    / Night
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    1 / 19
    4 of 5 stars (6) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic... View all property information
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    Key West, Florida Keys 33040
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    $1,506
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    1 / 30
    5 of 5 stars (3) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Grill
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    • Satellite TV
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    • Pets allowed
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    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West... View all property information
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    Key West, Florida Keys 33040
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    $917
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    1 / 30
    4 of 5 stars (2) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Pets allowed
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    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... View all property information
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    Key West, Florida Keys 33040
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    1 / 18
    4 of 5 stars (6) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Pets allowed
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    About this property
    Have you ever outgrown a favorite small space, and dreamed about transforming it into something larger and even better?  Wishing you could somehow magically gain enough room to expand it so it offered twice the space, while keeping all its original charm?  Well … that’s exactly what happened right... View all property information
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    Key West, Florida Keys 33040
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    $314
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    1 / 25
    4 of 5 stars (12) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
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    • ?
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    About this property
    DUVAL STREET HIDEAWAY: 2 story, 2 bedroom 2.5 bath rooftop townhome above Duval Square. Lots of upgrades in 2014 with new paint, beds, sofa. New Jacuzzi in February 2015.Open floor plan on the 1st level with kitchen, dining room, living room with sleeper sofa and half bath. French doors off... View all property information
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    Key West, Florida Keys 33040
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    $3,799
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Internet Access
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation... View all property information
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    Key West, Florida Keys
    From
    $426
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    1 / 7
    4 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
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    • Pets allowed
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    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,998
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    1 / 21
    4.5 of 5 stars (7) Very good
    7 Bedrooms / 7 Bathrooms / Sleeps 16
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    • Air Conditioning
    • Balcony
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    • Pets allowed
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    About this property
    Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and... View all property information
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    Key West, Florida Keys 33040
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    $589
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    1 / 10
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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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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    Location Information
    Key West, Florida Keys 33040
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    $3,275
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    1 / 26
    4.5 of 5 stars (8) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Private Outdoor...
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    • Pets allowed
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    About this property
    ATLANTIC BLUES - Stylish Conch cottage with hardwood floors, glass tiles, granite countertops and décor that is playful and soothing. Kitchen opens to the living and dining areas allowing the cook to remain part of the party. Step outside to the pool deck and splash in the heated dipping... View all property information
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    Key West, Florida Keys 33040
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    $2,751
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    4.5 of 5 stars (2) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Grill
    • Private Outdoor...
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    • Pets allowed
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    • x
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    About this property
    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway... View all property information
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    Key West, Florida Keys
    From
    $2,227
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    1 / 12
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    Just as you're inspired by an island oasis, so is this tropical Island Oasis Garden Home vacation rental. Cleverly hidden in the heart of Old Town Key West, this small private gated oasis uses a traditional Key West style architecture of tin roofs, wooden planking, sash windows, and charming front... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,572
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    1 / 36
    5 of 5 stars (1) Excellent
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Balcony
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in the heart of Old Town Key West. Here you will enjoy a completely private retreat with an atmosphere of wonderfully unchanged Caribbean charm. By combining Pavilion Villa and Down... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,506
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    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $347
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    1 / 26
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    About this property
    ISLAND WIND: 2 bedroom, 2 bath Bahamian-style townhome, with tin roof and white spindled decks. Snuggle into an oh-so-comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs with 2 twin beds; bathroom ensuite with entrance from the kitchen. Open floor plan... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,048
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    1 / 15
    5 of 5 stars (2) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Enquiry
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $491
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    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
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    About this property
    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,048
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    1 / 20
    3.5 of 5 stars (9) Average
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,572
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    1 / 24
    3.5 of 5 stars (4) Average
    7 Bedrooms / 5 Bathrooms / Sleeps 14
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
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    • Elder access
    • ?
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    About this property
    Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $3,013
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    1 / 25
    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    EMMA'S ESCAPE: 2 bedroom 1 bath condo in historic Bahama Village.The kitchen is well appointed and overall modern decor brings contemporary comfort to historic charm. Central a/c, flatscreen TV, WIFI and washer/dryer. Relax by the pool and hot tub or in the garden, a tropical oasis with seating... View all property information
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    Location Information
    Key West, Florida Keys 33040