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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 14
    4.5 of 5 bubbles (37) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    4.5 of 5 bubbles (33) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 bubbles (15) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 13
    5 of 5 bubbles (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    This is a lovely place to stay,well furnished, and ideally located right in the heart of the 'action'. However, it is quite expensive, with $25 per day parking charge plus...
    5 of 5 bubbles Reviewed 3 weeks ago
    5 stars. Great place, everything included, didn't have to bring anything. Old Florida style, best location, in the middle of all the action, balcony lets you view all. Restaurants...
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    1 / 14
    5 of 5 bubbles (25) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 14, 2017
    Rented this place for my sister's bachelorette party and we had an amazing stay. It really is walking distance to everything and the shared pool was great. It was such a bonus...
    4 of 5 bubbles Reviewed February 14, 2017
    Key West Bahama House is located in the perfect spot. Rooms are very nice and clean. The only downside in April of 2016, there was construction at the building behind and beside...
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    1 / 33
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    4.5 of 5 bubbles (78) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 6 days ago
    Thanks Steve and Sue. You made our stay in the Keys so memorable. Your condo was so well stocked and wonderful. We came with 2 children under 3 and they had a blast in the pool...
    5 of 5 bubbles Reviewed 4 weeks ago
    This condo has everything you need, from beach chairs to all your kitchen supplies. It was clean and bright. The pool was wonderful, and the location was quiet. You won't be...
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    1 / 39
    5 of 5 bubbles (36) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed November 21, 2016
    We were so thrilled to stay in this vacation rental, My mom is in a wheelchair full time and there was enough room for her to get around, the bathroom was perfect for her. My 2...
    5 of 5 bubbles Reviewed August 5, 2016
    Best aspect: owner Kathy W. communicated as stay got closer. She even asked how we were doing the day of travel and invited us to call her with any concerns or questions. We...
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    1 / 12
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 25, 2016
    Really enjoyed my stayed, I Will definitely will stay hear again, everything was just as expected, location was great, owner was fantastic and very helpful, apartment was very...
    4 of 5 bubbles Reviewed August 17, 2016
    Two bedroom, two bathroom condo suite with patio, across the street from the water. Each bathroom is connected to a bedroom, with the master bedroom having private access, of...
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    1 / 14
    5 of 5 bubbles (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 24, 2017
    We rented the condo and it was the best decision I've made! Mrs. Bonnie was very pleasant and explained all about the property. It was very clean and neat! It had enough utensils...
    4 of 5 bubbles Reviewed April 15, 2016
    The condo was clean and equipped with the necessities and a washer/dryer. Location is away from downtown but we knew that when we booked it. Would definitely rent again and price...
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    1 / 22
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 25, 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
    5 of 5 bubbles Reviewed November 22, 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
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    1 / 51
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Beautifully decorated by an interior designer. Custom bathrooms and modern kitchen with stainless appliances. Wireless Internet. This is your home... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed July 15, 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for the...
    5 of 5 bubbles Reviewed June 13, 2014
    This vacation rental was huge, nicely decorated, and a great place to stay. The pool, jacuzi, pool house, and courtyard were all amazing - so nice, we spent one full day just...
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    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Private Yard
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    • x
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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 / 26
    4 of 5 bubbles (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 9, 2015
    I just returned from a long weekend in beautiful Key West and the Verde Suite was a perfect choice. It was clean, comfortable and just far enough away from the hustle of the town...
    4 of 5 bubbles Reviewed June 30, 2015
    We really enjoyed our few days here and thank goodness for the refreshing pool because it was HOT HOT HOT! We enjoyed meeting a couple of other folks in the quaint cluster of...
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    1 / 39
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    5 of 5 bubbles Reviewed September 10, 2015
    Beautifully decorated Old Key West home. Our kids (12, 5) loved seeing the Iguana in the courtyard. The pool was nice to relax in after a day of sightseeing. Beds were...
    5 of 5 bubbles Reviewed September 9, 2015
    We brought my daughter, her best friend, and her boyfriend to Key West to celebrate her 21st birthday. The pool was a welcome retreat from the heat and the pub crawls. The...
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    1 / 26
    4.5 of 5 bubbles (27) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Hibiscus Hideaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St. Welcome to the perfectly located and affordable apt Hibiscus Hideaway. You will not find a better spot to spend your sunny days and exciting... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 13, 2015
    Loved this condo for our Keys getaway!! This place was perfect for our 5 day getaway and it's just 2 blocks from Duval. Very easy check in process took maybe 5 min at the most...
    5 of 5 bubbles Reviewed August 19, 2015
    We have stayed at Courtney's Place and another place farther down on Duval in the past. Hibiscus is closer to the "action" on Duval. Hibiscus is a unit for 2 people. The place...
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    1 / 33
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 9, 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 bubbles Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
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    1 / 52
    5 of 5 bubbles (14) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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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 January 1, 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 September 3, 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
    3 Bedrooms, 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 April 21, 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 March 5, 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 / 14
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed February 9, 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 bubbles Reviewed December 29, 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 30
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    • x
    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 / 33
    4.5 of 5 bubbles (4) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed December 12, 2015
    First impression was that room smelled clean. Very secluded and minutes from Duval Street. Second night, noticed a lot of critter activity. Small bugs and roaches. Management...
    5 of 5 bubbles Reviewed October 17, 2014
    We had an excellent experience staying in this studio for our honeymoon. Only drawback was the lack of kitchen equipment which made it difficult to cook a full meal for...
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    1 / 27
    4.5 of 5 bubbles (32) Very good
    1 Bedroom, 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 May 19, 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 February 1, 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 / 39
    4.5 of 5 bubbles (10) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    4 of 5 bubbles Reviewed January 13, 2015
    Great location! 1/2 a block off the main street (Duval) and convenient to everything, but in a quiet dead end street. Private parking! (Hard to park anywhere in the Keys...
    5 of 5 bubbles Reviewed January 12, 2015
    Its just a few steps away from where all the actions is. Considering the location, it is actually quiet at night. We got ourselves lock out while drinking and partying at the...
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    1 / 23
    4.5 of 5 bubbles (22) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed February 4, 2017
    We stayed at this cottage for a couple nights. It was cozy and well kept. The kitchen had everything you'd need to cook an average meal. The cottage definitely could have used a...
    5 of 5 bubbles Reviewed December 8, 2014
    The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 2 weeks ago
    The townhouse on Stock Island (Key West) met all of our needs. It was clean, roomy and convenient. Having 3 full baths was a real plus for 6 women. The pool was delightful...
    5 of 5 bubbles Reviewed November 12, 2016
    House was very clean and the owner was very helpful and responsive. I would definitely stay again and would highly recommend it to anyone going to key West !
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    1 / 24
    4.5 of 5 bubbles (31) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed January 16, 2015
    This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and walk...
    5 of 5 bubbles Reviewed November 17, 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a long...
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    1 / 23
    5 of 5 bubbles (2) 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 5 days 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 January 26, 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 / 25
    4.5 of 5 bubbles (14) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork sandwiches and homemade ice-cream at the... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed May 4, 2016
    This quaint villa was perfect for our party of 2 (might be a bit crowded for 4 adults, but for 2 kids it should be just fine!) The 1/1 was well appointed with everything we needed...
    5 of 5 bubbles Reviewed September 21, 2015
    We loved our stay here. It was decorated nicely, clean, and quiet. Housekeeping came in daily and did a good job. I liked the setup of the condo a lot; a nice, spacious...
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    1 / 27
    4.5 of 5 bubbles (8) Very good
    2 Bedrooms, 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 July 10, 2016
    Our only wish is for additional air conditioning units in living area and bathroom. Everything else was wonderful
    4 of 5 bubbles Reviewed July 21, 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 / 28
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed July 31, 2015
    We found this place very cozy and well located. It was clean and very spacious for two people. The air conditioner wall was a little noise, but it didn't bother us much because we...
    4 of 5 bubbles Reviewed June 4, 2015
    More space than a hotel room for less money than we usually pay. Convenient location to Duval. Quiet neighborhood. No closet door, beads hanging instead. When air conditioner...
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    1 / 34
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropical setting. The living... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed August 22, 2016
    Love the place! Location was good. There was an issue with ants in the kitchen. Also, I was issued 3 keys and 1 of the keys was not for our place. Changed the key with...
    5 of 5 bubbles Reviewed April 21, 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 particular cottage but our guests had rave...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    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
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed May 16, 2016
    Sandy and her team at Curry House are friendly, helpful and welcome you to the B & B with a warm smile and they give you a hug when you leave. I went with my partner and our room...
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    1 / 22
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 24, 2016
    Fantastic. No other word describes it better. The view, the amenities, the layout of the condo...all fantastic. Owner is a very nice lady too. Very easy to deal with. Will...
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    1 / 27
    4.5 of 5 bubbles (21) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    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 December 11, 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 October 25, 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    1 / 21
    5 of 5 bubbles (25) Excellent
    1 Bedroom, 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 October 8, 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 August 19, 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 / 29
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 6 days ago
    Our location was the Sunrise Suite located one mile from the Airport. The place was clean and comfortable. Every time we needed a ride to Old Town, Steve always deliver and on...
    5 of 5 bubbles Reviewed May 12, 2016
    We're the type of people who like to be away from the massive partying, and this was the perfect location. Even though you always can't get away from it completely, we feel like...
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    1 / 30
    4.5 of 5 bubbles (3) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off by... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed May 16, 2016
    As far as the accommodation is concerned, the location is unsurpassed. The cottage is clean, comfortable and well appointed. Sadly what let's the place down are the agents/support...
    5 of 5 bubbles Reviewed November 11, 2015
    This is the second time we've stayed in this rental complex. The first time upstairs and now this time in the back. The location off of Whitehead is perfect for everything we love...
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    1 / 30
    4.5 of 5 bubbles (8) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 bubbles Reviewed January 13, 2015
    Well, talk about HIGH season. Prices are dear and the lines of cars down the highway get longer each day between Xmas and New Year's. But Key West is a special place, at least Old...
    5 of 5 bubbles Reviewed December 23, 2014
    Stayed for a week before Christmas 2014. I did a bit of research on different properties/hotels, and really wanted to get away from the traditional 'resort' style accommodations...
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    1 / 99
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • x
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    • x
    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed January 3, 2017
    This is a nice spot right of strip. Place is more for a family w young kids. Third bedroom is kinda small. Other than that place was real confronting. Enjoyed how close to...
    4 of 5 bubbles Reviewed November 9, 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
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    1 / 26
    4.5 of 5 bubbles (42) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed November 17, 2016
    Not even a block off Duval near the Southernmost end of the island (i.e., the quiet end of Duval), this efficiency was a great find. Located in a renovated old house with...
    3 of 5 bubbles Reviewed November 10, 2016
    The location is great. Right next to duval street. But it's definitely too small even for 4 persons.... we were walking in each other. One fan wasn't working and in the kitchen...
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    1 / 36
    4.5 of 5 bubbles (14) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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 November 9, 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 August 12, 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 / 29
    4.5 of 5 bubbles (32) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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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 June 14, 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 November 11, 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 / 22
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    About this property
    Cozy Condo in Prime Location! Right off of Duval Street! Located just steps off of world famous Duval Street, Duval Canopy is the perfect blend of comfort, location and value. Just a few blocks from The Southernmost Beach, the Southernmost Point, and other favorites like The Butterfly Conservatory... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (39) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    • x
    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 March 4, 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 February 28, 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 / 33
    4.5 of 5 bubbles (30) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This immaculately clean and comfortable well air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a new Queen Sleeper Sofa with gel memory foam mattress. The efficiency... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed December 1, 2014
    Wonderful location, quiet. In desperate need of upgrades, 2 burner stovetop not fixed but portable one available, ac in bedroom starts and stops every 5 minutes...several cracked...
    4 of 5 bubbles Reviewed November 17, 2014
    Nice,good location but no parking onsite 95% of time. Had to park 2 blocks away. Cooktop did not work so had to use portable 110 volt spare.
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    • Peak travel: March - April
    Key West Vacation Rentals and Condos

    Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

    Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

    Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

    Where To Rent a Vacation Home in Key West

    Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

    Many House Rentals Near Attractions and Activities For All Ages

    Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

    Key West Bars and Restaurants

    Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

    Book a Key West Vacation Rental For Your Next Trip

    Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.