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Holiday Rentals in Key West

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 10
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 28
    5 of 5 bubbles (3) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    • Patio
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    • Private Outdoor...
    • Washer
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    • DVD Player
    • Hot Tub
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    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (37) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (47) Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Air Conditioning
    • Terrace
    • Private Outdoor...
    • Balcony
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    • x
    About this property
    Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the action at Duval Square just south of Truman. The residential units sit in a courtyard setting above a retail/office courtyard below with the shared pool... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Balcony
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    • Terrace
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    • x
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    • x
    About this property
    30- Night minimum stay: Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Beautifully decorated with palm tree décor, leather sleeper sofa,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Porch
    • Internet Access
    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Coastal on Coral is located in the beautiful gated community of Coral Hammock on the Quiet end of Key West on Stock Island.This home has all the amenities of a house and a resort combined boasting 3 bedrooms,all with 40"flat screen televisions and each with it's own full bath.A 55"smart television... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Porch
    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to Paradise a lovely place to call home for a month* or more in Key West! Just minutes from the excitement of Duval Street, the NY caliber plays at The Waterfront Theatre, exceptional fishing and swimming in the turquoise waters … Yet nestled in the serene environment of the KW Golf Club... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4 of 5 bubbles (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • Internet Access
    • Balcony
    • DVD Player
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Shared Outdoor Pool...
    • Hot Tub
    • Parking
    • Air Conditioning
    • Patio
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located right in the heart of old town Key West. Park your car in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    4.5 of 5 bubbles (15) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Terrace
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers a well- equipped kitchen, a living room that opens to a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4.5 of 5 bubbles (16) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a four bedroom, four bath classic "eyebrow" style home located in historic Old Town Key West. This home is just 1 block off Duval Street and a short walk to Harbor Walk & Mallory Square. Enjoy Simonton... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Hot Tub
    • Waterfront
    • DVD Player
    • Sauna
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful ocean front condo. Great view, beautiful pool and hot tub. Area for BBQ. Close to to Duval st. Call or email for more details and picture. Beds: 1 King Bed, 1 Twin Bed, 1 Sofa Bed View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4 of 5 bubbles (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Discover paradise of Key West in a distinctive setting. Luxury, large two-bedroom, two-bath, (sleeps 6) condominium set in a tropical garden with a large balcony. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room, dining area and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 55
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Satellite TV
    • DVD Player
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    GALLEON RESORT MARINA PENTHOUSE with LOFT 2BR/2BA RENTAL OVERLOOKING SEAPORT MARINA 5th FLOOR SUITE RENTAL / $3,750 (SLEEPS 8) / F-53 Week 2 Jan 13-20, 2018 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout (See attached suite photos) 1 of only 7 loft suites in the 96-unit... View all property information
    Location Information
    Key West, Florida Keys 33040
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