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Key West House Rentals

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    1 / 39
    4.5 of 5 bubbles (16) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 39
    4.5 of 5 bubbles (10) Very good
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 30
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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 waterfall feature(shared... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 2 weeks ago
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This beautiful motor yacht is available for your exquisite Key West vacation! . Huge Salon, Large galley, gorgeous teak throughout. One queen bedroom and one full bedroom with bathrooms for each one. Forward on the bow are 2 very comfortable loungers with pillows for relaxing. The upper deck is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 4 weeks ago
    Staying on this yacht was a wonderful experience! We stayed at the dock and could walk to the restaurant (Dante's) and pool. I went fishing and could take my catch to Dante's...
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    1 / 34
    4.5 of 5 bubbles (23) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Abaco Suite, is a bi-level suite with a very spacious... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 June 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space, decent...
    5 of 5 bubbles Reviewed 30 May 2015
    As good as the unit was and it really was its the people behind the organisation that make the difference ! I had stuffed up my original booking by 4 weeks, hey I'm old, it's...
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    1 / 21
    5 of 5 bubbles (25) Excellent
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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! The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 8 October 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    5 of 5 bubbles Reviewed 19 August 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    1 / 52
    5 of 5 bubbles (14) Excellent
    Studio, 4 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
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    About this property
    Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 January 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    5 of 5 bubbles Reviewed 3 September 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    1 / 25
    5 of 5 bubbles (4) Excellent
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information. I did not stay in this cottage but our guests had rave reviews and I...
    5 of 5 bubbles Reviewed 5 March 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
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    1 / 31
    4.5 of 5 bubbles (12) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 4 January 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    5 of 5 bubbles Reviewed 5 June 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    1 / 30
    4.5 of 5 bubbles (49) Very good
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 28 January 2016
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while the...
    3 of 5 bubbles Reviewed 2 December 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
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    1 / 29
    4.5 of 5 bubbles (32) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 14 June 2016
    Beautiful home. We hated to leave. The property is well kept and the accommodations were beyond our expectations. We had our own private pool to lounge in and enjoy after long...
    4 of 5 bubbles Reviewed 11 November 2014
    The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
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    1 / 27
    4.5 of 5 bubbles (8) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 10 July 2016
    Our only wish is for additional air conditioning units in living area and bathroom. Everything else was wonderful
    4 of 5 bubbles Reviewed 21 July 2014
    Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
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    1 / 27
    4.5 of 5 bubbles (32) Very good
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 Caribbean colors and wood floors. Key West Vacation Rentals... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 19 May 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected). The...
    4 of 5 bubbles Reviewed 1 February 2016
    This is the second time my husband and I have stayed at one if the units in the Villas. The location is fantastic - walk to the action on Duval or the beach. And the property...
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    1 / 28
    4.5 of 5 bubbles (14) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 August 2016
    My friends and I went on a wonderful 4 day trip to Key West. We stayed at the Du Pont house which was perfect for 5 people as there were 2 bedrooms and one pull out couch. The...
    4 of 5 bubbles Reviewed 16 June 2016
    Five of us stayed here for 3 nights and we loved it! The location is fantastic, it's a block off of Duval street so you can walk everywhere. The whole place is nicely decorated...
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    1 / 32
    4.5 of 5 bubbles (39) Very good
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.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! Downstairs is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 4 March 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    3 of 5 bubbles Reviewed 28 February 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
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    1 / 27
    4.5 of 5 bubbles (21) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute walk 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
    5 of 5 bubbles Reviewed 11 December 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    5 of 5 bubbles Reviewed 25 October 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    1 / 26
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (16) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    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 King pillow top bed upstairs, another... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 28 June 2016
    This house had a wonderful location. It was very easy to walk to Duval Street and the Southernmost Point. The beds were comfortable, but the house inside and out needs updating...
    5 of 5 bubbles Reviewed 1 July 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
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    1 / 36
    4.5 of 5 bubbles (14) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    3 of 5 bubbles Reviewed 12 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
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    1 / 23
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    Our vacation at Key West Oasis was definitely one of the best trips we’ve ever been on. From start to finish it was the perfect trip. I spoke with Kim when I booked the trip and...
    5 of 5 bubbles Reviewed 26 January 2016
    This great rental was even better than advertised. It offered total peace and privacy with the private back yard and pool, and cottage with a second bedroom and outdoor shower...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group had...
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    1 / 28
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 23 January 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    1 / 21
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This 1 bed 1 bath home is the perfect home for you to enjoy Key West and all it has to offer. Located just steps from the World-Famous Duval St. you will find yourself in one of the most desired locations in Key West. Downstairs in this home you will find a full kitchen and comfortable living... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (13) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    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
    4 of 5 bubbles Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a place...
    4 of 5 bubbles Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    1 / 33
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (8) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 shotgun architecture with a front... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 30 October 2016
    The management staff were very friendly. The house is right on Truman st. A couple of feet from Duval St. House as pictured in ad. We were a total of 8 people 5 adults and 3...
    5 of 5 bubbles Reviewed 25 July 2014
    This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a great...
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    1 / 35
    5 of 5 bubbles (6) Excellent
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 23 August 2016
    Alexandria's Secret is a wonderful place to stay. You are 1/2 block to Duvall St, walking distance to attractions, you have your own private pool and outdoor living space with a...
    5 of 5 bubbles Reviewed 4 August 2016
    If you're going down to Key West, you must stay here. It's a beautiful house right off of Duval. It's on the far side, but we were still able to walk all the way to Mallory Square...
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    1 / 38
    4.5 of 5 bubbles (3) Very good
    Studio, 2 Bathrooms, Sleeps 12 | Quick View
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    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
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 29 July 2014
    Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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    1 / 31
    4 of 5 bubbles (24) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 22 January 2015
    We just spent a week at SMR and really enjoyed our stay! Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
    4 of 5 bubbles Reviewed 23 November 2014
    Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub which...
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    1 / 41
    4 of 5 bubbles (20) Very good
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, and a/c.. The upstairs large tiled walk-in shower with hair-dryer makes this private... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 30 October 2015
    This is our second year at this location. This year we chose the Havana Suite. The unit was extremely clean and pleasantly decorated. Very nice kitchen. TVs in the bedroom and...
    4 of 5 bubbles Reviewed 27 April 2015
    We chose Little Havana initially because of the location. It is a smidgen off the beaten path from the hustle and bustle of the Duval action, yet within walking distance to a lot...
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    1 / 30
    4 of 5 bubbles (1) Very good
    Studio, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm, Traveler's Palm, and Royal Palm which can all be booked individually. All together, these three units have 5 separate bedrooms, 3 separate hot tubs, and share an incredibly luscious,... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 11 May 2015
    We took over the whole compound with three generations of our family - my family and 4 month old twins in the attic suite, my sister's family and the grandparents on the first...
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    1 / 22
    4 of 5 bubbles (37) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 15 December 2015
    We stayed in this property for two days. We had a good time. Staff is friendly. They have everything what we need there. I read reviews about this property and some one mentioned...
    4 of 5 bubbles Reviewed 11 December 2015
    Nice location. Hot tub, patio nice, porch fun to watch traffic a passerbys with morning coffee. Houe is cute but needs a little TLC. Fingerprints on walls and doors, missing...
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    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This 4 bedroom 3 bath home is located in Key Haven (mile marker 5) Key West. Key Haven is a quiet neighborhood Great for boating, snorkeling, diving, fishing, biking, walking or just relaxing in the hammocks. Easy boating access to the Gulf and Atlantic (one canal from open water). Just 4 miles... View all property information
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    Key West, Florida Keys 33040
    1 / 36
    3.5 of 5 bubbles (3) Average
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been transformed with bits and... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 15 June 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    5 of 5 bubbles Reviewed 29 July 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    1 / 31
    4 of 5 bubbles (11) Very good
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    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 bars, shops, and fine dining.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 16 July 2016
    Close to where we want to be. Have booked this place twice in two years. And plan to rent again for our annual trip.
    4 of 5 bubbles Reviewed 15 May 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
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    1 / 29
    4.5 of 5 bubbles (12) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    5 of 5 bubbles Reviewed 6 June 2016
    Absolutely loved the place. We were a group of 5 girls and we found the villa really comfortable, spacious, clean and well stocked with towels, toiletries and kitchen...
    5 of 5 bubbles Reviewed 18 September 2015
    We had a group of girls and we wanted to be close to Duval but also have a pool. The pictures almost don't do it justice. It was awesome. The beds were very comfortable. Two...
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    1 / 27
    4.5 of 5 bubbles (50) Very good
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 16 December 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You will...
    5 of 5 bubbles Reviewed 24 July 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    1 / 26
    5 of 5 bubbles (39) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 11 February 2017
    Well maintained. Well furnished.Well equipped In the center of the action Duval street. Very pleasant stay You got to love Hemingway Monique.
    5 of 5 bubbles Reviewed 8 January 2017
    This is the 3rd time we have rented Casa del Sol, The House is great. the rooms are comfortable. the location is great - 2 blocks from Duvall Street in Old Town. Once at Casa...
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    1 / 32
    4.5 of 5 bubbles (3) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    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 3 bedroom home includes 2 bedrooms in the main house and an additional mother-in-law suite by the pool. Each bedroom features... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 13 October 2014
    The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
    5 of 5 bubbles Reviewed 25 July 2014
    I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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    1 / 38
    4 of 5 bubbles (17) Very good
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    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
    5 of 5 bubbles Reviewed 27 January 2017
    My friends and I have traveled to Key West for the past three years and we always rent through KWVR. Each year we have rented a different property however this property is...
    4 of 5 bubbles Reviewed 18 August 2016
    Stayed here with friends. The setup was perfect for our needs - one couple and two singles. My bed was very comfortable. The only thing missing in my room was a mirror! The...
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    1 / 16
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
    • Ocean Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 29 December 2016
    This location is in Stock Island close to airport, beaches and all the attractions. Exceptionally clean accommodations and was very safe. The pool at the unit was breathtaking. We...
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    1 / 25
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    In one of the most desirable locations in Key West, you will find the exquisite 2CoolFish. Located in Truman Annex. Just walking into this pristine home will take your breath away. Featuring two bedrooms and one and a half bathrooms, this home is perfect for a family or small group of friends... View all property information
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    Key West, Florida Keys 33040
    1 / 7
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (21) Very good
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 15 August 2016
    This is a very nice property in a quiet part of Old Town. We enjoyed the pool and chose the o cool in a couple of nights so it was easy. Great stay.
    5 of 5 bubbles Reviewed 18 May 2014
    Read the title. Would do it again. In a heartbeat. Clean, well-equipped, met ALL OF OUR NEEDS. Whether a family with children, or friend getaway, meets all needs.
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
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    • Pet-friendly
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    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (1) Very good
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 13 May 2016
    The house was really nice. The owner and the property manager (NOT Tim from Historic Hideaways) were very helpful when we couldn't figure out the TVs and ALL the remotes!! Lol I...
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    1 / 21
    4.5 of 5 bubbles (21) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around... View all property information
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    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 8 November 2016
    This was a nice house with lots of convenience. The swimming pool is not so great and the water is freezing so you really cannot enjoy the pool at all. The back deck is very...
    5 of 5 bubbles Reviewed 11 June 2015
    We stayed in the Meadows house in June and loved everything about the location, the house, the pool and yard and the BBQ. The house has so much personality, the rooms are...
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    1 / 38
    Studio, 6 Bathrooms, Sleeps 22 | Quick View
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    • x
    About this property
    Papa's Hideaway is a Guesthouse property comprised of Garden of Eden, Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls, and Islands in the Stream. This private compound had a large outdoor gathering area around your private pool equipped with Grill, Sundeck, and Bar. Located on a... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 3 weeks ago
    The house was gorgeous, and the sunset view from the balcony lived up to expectations... Short walk to Duval Street... Totally recommended
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