We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Key West House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $477 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    View Map
    More filters
    loading...
    Travellers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 24
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    $9,368
    / Month
    Payment Protection
    View Details
    View Details
    1 / 32
    4 of 5 stars (20) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $273
    / Night
    Payment Protection
    View Details
    View Details
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $231
    / Night
    Payment Protection
    View Details
    View Details
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $259
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Patio
    • Terrace
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home 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
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 stars (20) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $535
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $427
    / Night
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Balcony
    • Washer
    • Grill
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was... View all property information
    Location Information
    Key West, Florida Keys
    1 / 30
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $590
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Grill
    • Patio
    • Parking
    • Air Conditioning
    • Balcony
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    From
    $4,822
    / Month
    View Details
    View Details
    Amenities & Details
    • Terrace
    • Balcony
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 stars (31) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $273
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Parking
    • Air Conditioning
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    From
    $4,822
    / Month
    View Details
    View Details
    Amenities & Details
    • Terrace
    • Internet Access
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Owner online now
    From
    $204
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Paradise Palms is decorated in a tropical motif, with a palm matelassé and herb-green pinstriped bed skirt. There are wood furnishings throughout, along with nautical prints and souvenirs. Double doors open onto our second story landing where you are only steps away from the upper sun deck of our... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $4,133
    / Month
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $342
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Patio
    • Air Conditioning
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    $426
    / Night
    View Details
    View Details
    Amenities & Details
    • Terrace
    • Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished... 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
    $344
    / Night
    View Details
    View Details
    Amenities & Details
    • Shared Outdoor Pool...
    • Balcony
    • DVD Player
    • Internet Access
    • Satellite TV
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4 of 5 stars (14) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $413
    / Night
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Balcony
    • Terrace
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    From
    $4,822
    / Month
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 46
    5 of 5 stars (1) Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
    Owner online now
    From
    $1,347
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Balcony
    • Parking
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation. Old Town Garden Villas is comprised of the following... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 41
    4.5 of 5 stars (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    other traveller has booked this property
    Owner online now
    From
    $686
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $562
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Grill
    • Patio
    • Satellite TV
    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
    Location Information
    Key West, Florida Keys 33040
    Get the List
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Owner online now
    From
    $204
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Patio
    • Internet Access
    • Air Conditioning
    • Terrace
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of Banana's Foster Guest House This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Owner online now
    From
    $190
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    From
    $4,519
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Satellite TV
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    3 of 5 stars (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $827
    / Week
    View Details
    View Details
    Amenities & Details
    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living the Key West Life to it's fullest in this highly desired walking... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $6,888
    / Month
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $548
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $424
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Parking
    • Patio
    • Internet Access
    • Grill
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
    Location Information
    Key West, Florida Keys
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
    other traveller has booked this property
    Owner online now
    From
    $1,540
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Internet Access
    • Terrace
    • Grill
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $8,266
    / Month
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Terrace
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in Big Coppitt is this secluded, waterfront paradise. This 3 bedroom, 3 bathroom house features a private pool. Relax in the grand outdoor patio area overlooking the pool and canal. Each of the three bedrooms has its own private bathroom. Located on the ground floor is the living room,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $289
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool...
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (5) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    $1,061
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor...
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
    Location Information
    Key West, Florida Keys
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    $6,888
    / Month
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Paradise at its finest is exactly what you can expect from this exquisite and unique home. Sunset Key Overlook is a stunning two bedroom, two and a half bathroom house on a private island, in Key West. Enjoy access to private owner’s beach on western facing side of island with beautiful sunset... View all property information
    Location Information
    Key West, Florida Keys 33040
    11 Bedrooms, 9 Bathrooms, Sleeps 32 | Quick View
    Owner online now
    From
    $1,995
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. Located at 706 and 708 South St - near The Southernmost Point - this nightly group unit is the perfect getaway spot for large groups of friends and family. COTTAGE @ TROPICAL VILLAGE:... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $6,888
    / Month
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Behind the white picket fence sits this beautiful executive pool home in New Town. This three bedroom, two bathroom home has a custom kitchen with full pantry adjacent to the large dining and living room. The master suite has an oversized bathroom with jet tub and glass shower, a walk in closet... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    other traveller has booked this property
    Owner online now
    From
    $1,072
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Patio
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $548
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
    Location Information
    Key West, Florida Keys
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $6,199
    / Month
    View Details
    View Details
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Terrace
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then cook some of the catch out on your deck with a few... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4 of 5 stars (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $1,113
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located at 729 Whitehead St, 'Southern Palms' is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (31) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $714
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Private Outdoor...
    • Patio
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $686
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Both bathrooms completely renovated as of September, 2015*** 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (72) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $413
    / Night
    View Details
    View Details
    Amenities & Details
    • Porch
    • Internet Access
    • Air Conditioning
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way,... View all property information
    Location Information
    Key West, Florida Keys
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Owner online now
    From
    $245
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Room Seven is a magnificent room on the third floor with unique and fun architecture. It is painted in a tropical green tone that is soothing and a lovely contrast to the tropical greens of Key West. The private bath will make this room an exceptionally comfortable home away from home. This room... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $397
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (14) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Owner online now
    From
    $562
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Balcony
    • Internet Access
    • Air Conditioning
    • Patio
    • Terrace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (50) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $586
    / Night
    View Details
    View Details
    Amenities & Details
    • Porch
    • Private Outdoor...
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special... View all property information
    Location Information
    Key West, Florida Keys
    1 / 30
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    $6,888
    / Month
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Parking
    • Shared Outdoor Pool...
    • Air Conditioning
    • Patio
    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.*** 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
    1 / 24
    4.5 of 5 stars (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $7,426
    / Week
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    • Grill
    • 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
    Location Information
    Key West, Florida Keys
    1 / 20
    3.5 of 5 stars (9) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    From
    $1,102
    / Night
    View Details
    View Details
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $317
    / Night
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (12) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $951
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Wi-Fi
    • Washer
    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
    Location Information
    Key West, Florida Keys