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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 28
    4 of 5 stars (8) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 28
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    1 / 25
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 17
    4 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 1, 2013
    Oh my goodness... When we made plans to go to Key West, we wanted to kayak, snorkel, seaplane to Dry Tortugas, and never did one of these things. This condo was so addictive...
    5 of 5 stars Reviewed March 6, 2013
    We were more than pleased with our unit and with the pre-checkin service provided by Rent Key West Vacations. The view of the ocean could not have been better unless you were on...
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    1 / 10
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 15, 2015
    The owners could not have been nicer. Clean, right downtown, close to all the action in town. Going to make it back and stay here again.
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    1 / 10
    4.5 of 5 stars (49) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed November 21, 2014
    My husband and I recently enjoyed a wonderful week long stay at this condo in Key West! We certainly made the right choice when selecting Colony Poolside for our vacation. This...
    5 of 5 stars Reviewed August 30, 2014
    Just a few minutes walk from duval, a perfect balance of having all the bars etc nearby, but peaceful enough when sitting out by the pool that you're not disturbed by noise...
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    1 / 27
    4.5 of 5 stars (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 stars 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 stars 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 / 10
    5 of 5 stars (41) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 5, 2015
    We enjoyed our stay at Shipyard 253. It is a nice two bedroom/one bath with a great location only two blocks from Duval and situated in the middle of the strip. Was very clean...
    5 of 5 stars Reviewed July 30, 2013
    Shipyard 253 was in the perfect location. We were able to walk to Duvall Street, Fort Zachary Beach and South Beach. The condo was equipped with everything we needed for the week...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Caribbean Dreams is an inviting space, decorated in rich wood and cane furnishings, perfect for your Key West vacation! Just a few steps up from the garden entry path, 'Caribbean Dreams' offers a calm and cozy atmosphere. Enjoy the ultra comfy queen sized bed, free wifi, and daily housekeeping.... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
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    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Waterfront
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    About this property
    Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2016! Max occupancy: 2 couples or 1 couple with up to 3 children under 12. The calendar on this site shows availability. We do not take partial weeks or bookings of less than 7 nights unless it is between... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    We had such a great time staying on the Key West Yacht and Breakfast, It was definitely a different experience staying on a boat but we had such an amazing time. It was so nice...
    5 of 5 stars Reviewed May 26, 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places and...
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    1 / 28
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 1, 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...
    5 of 5 stars Reviewed February 4, 2014
    We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
    • Terrace
    • Outdoor Dining Area
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    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 10, 2014
    Location of Tobago house is excellent if you like to be close to restaurants, beach, and all that key west has to offer. Leave your car at home as parking is difficult. The house...
    4 of 5 stars Reviewed March 12, 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
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    1 / 20
    5 of 5 stars (25) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars 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 stars 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 / 26
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which features outdoor seating and a Gas BBQ Grill, making your... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 31, 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    3 of 5 stars Reviewed March 15, 2014
    We have stayed all over Key West over the last 20 years and always liked the Truman annex area so decided to try it out. Well this is actually in Shipyard Condo area next to...
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    1 / 22
    4.5 of 5 stars (72) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Porch
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    About this property
    Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way,... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed September 14, 2015
    Rose Cottage was a wonderful place to stay! We visited during the off season for our anniversary/birthday, and enjoyed the privacy and peacefulness of the cottage surroundings...
    5 of 5 stars Reviewed September 13, 2015
    Hard to believe that this quiet little cottage is just a half block off of Duval on an alley that runs between Fat Tuesdays and Hard Rock Cafe. We've stayed here many times and...
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    1 / 28
    4.5 of 5 stars (48) Very good
    3 Bedrooms, 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 stars Reviewed 1 week ago
    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 stars Reviewed December 2, 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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
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    Key West, Florida Keys 33040
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    1 / 17
    4 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Bright, tropical colors and tile floors provide an island ambience to... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 27, 2014
    This unit has recently been refreshed and is very comfortable. It has everything you need to have a perfect vacation. The kitchen is well stocked, if you are inclined to do some...
    4 of 5 stars Reviewed May 2, 2013
    The location was great, Smathers beach is awesome and right across the street. we were a short bike ride from everything. The rental agency was great and very responsive. The unit...
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    1 / 35
    5 of 5 stars (13) Excellent
    2 Bedrooms, 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 stars 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 stars 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 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (38) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 26, 2015
    Wonderful property, great location for walking around Key West. Rooftop deck for morning coffee and enclosed patio. Parking is at a premium, especially around the property, so...
    5 of 5 stars Reviewed November 4, 2014
    My wife and I stayed at the Sunset Suite - Nightly which is managed by Key West Vacation Rentals. This was our first trip to Key West as we went for the Meeting of the Minds. We...
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    1 / 21
    4.5 of 5 stars (37) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 7, 2014
    1960s property but well maintained with a good pool, new gas grills (all the better for cooking your catch) and located right on the marina. Our unit (1040) was on the first floor...
    4 of 5 stars Reviewed September 9, 2013
    had a great time, I'll be back.
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    1 / 22
    4.5 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    First floor corner condo perfect for 2 plus space for visiting friends and family! A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic Key West, you will be only 4 blocks from world famous Duval Street and 3 blocks away from the scenic Historic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    We needed a place to stay for a month and boy are we glad we found this one! Close enough to walk to everything, yet in a very secluded and quiet area. Comes with an off street...
    4 of 5 stars Reviewed April 26, 2014
    Very nice condo with huge pool area. Very clean and neat. We loved the location! We would love to go back again some day. The only negative was the living room furniture. It...
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    1 / 32
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 2 weeks ago
    The property was great. A few issues with C120. The fridge had rust. The TV in the living room was computer monitor sized. We like to catch a game now and then and it was like...
    5 of 5 stars Reviewed January 4, 2016
    The onsite property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the...
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    1 / 12
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 7, 2015
    We went over the 4th of July weekend with a group of friends. Location is still amazing. The major concern was the it never felt as if the AC was cold enough. I am wondering if...
    4 of 5 stars Reviewed April 24, 2015
    Cute two story Key West cottage. Located blocks away from Duval, but yet quiet. Good times were had at the Jacuzzi and the top patio. The swing on the top balcony was nice and...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm 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 and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large... View all property information
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    Key West, Florida Keys 33040
    1 / 39
    4 of 5 stars (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 stars Reviewed January 22, 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 stars Reviewed November 23, 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 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Cleverly hidden from view at the end of a narrow island urban lane that intersects with downtown Duval Street, this Starlight Siesta vacation rental encompasses the rear half of the Key West penthouse property known as Penthouse On Duval. Perfectly staged in the island's city center, this... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. The front porch is perfect for people watching and chatting with locals passing by. Once you step into the open... View all property information
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    Key West, Florida Keys
    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    You have use of one of four private cabins with a private marine style bathroom. Three cabins available for rent. You will share the common areas with new friends. The cabin is air conditioned with a queen like bed. Captain Charles and wife Deborah use one cabin. When conditions allow we offer a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 29, 2015
    Five of us stayed on the Anna B over the weekend. It is a very nice catamaran sailboat, clean and well maintained. Each stateroom had fresh linens, its own en-suite bathroom, and...
    5 of 5 stars Reviewed May 28, 2015
    Our stay was wonderful! It's was clean, quaint & relaxing! I hope to return soon. Captain Charles was a pleasure to speak to!
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    4 of 5 stars (37) Very good
    2 Bedrooms, 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 15, 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 stars Reviewed December 11, 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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic home. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front entrance with sweeping front porch over Caroline Street- this... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor.... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 stars (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Part of the Nightly Group PALM GARDENS 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... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars 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...
    4 of 5 stars Reviewed September 9, 2015
    We could not have been more pleased with the rental process at Palm Isle. It was a very clean and well appointed condo, centrally located to the Island. It was close enough to the...
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    1 / 15
    4.5 of 5 stars (47) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 2, 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    4 of 5 stars Reviewed February 7, 2013
    Stayed here for two weeks while attending a meeting in Key West It was a perfect little cottage in a grouping of cottages with a shared pool, laundry and beautiful gardens. Our...
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    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Nestled in one of Key West's original gated 'mini-compounds,' the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'... View all property information
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    Key West, Florida Keys 33040
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
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    About this property
    I am happy you found this great Ocean View stay! Love to answer your Questions-fast- don't lose your dates just phone hurry! Scuze’ for site inconvenience. Because of variables happy to discuss anything further on this [by phone only] 3 blocks from Duval st. OCEAN VIEWS GALORE! although Not A... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    One week available April 24th to May 1st, Sunday to Sunday. I have a 2 bedroom, 2 bathroom, Full Kitchen Timeshare for rent, Hyatt Beach House in Key west. Resort is on the gulf of Mexico. Room assigned at check in. Rooms look over resort with a 10 X 10 screened in furnished balcony. Units have... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm 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 and bask... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 29, 2015
    We came in a small plane, so we needed to ship our luggage down to Key West. The office staff allowed us to ship it right to the check in office. The suite had two rooms and a...
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    1 / 20
    5 of 5 stars (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. Additional amenities include: sofabed, coffee maker, nearby beach, nearby bank, nearby internet cafe, ice maker, near beach, nearby medical... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars 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 stars 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 / 27
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 12, 2015
    We visited the Annex for Fantasy Fest a few years back. The location is perfect! Close enough to the action of the main streets, but private enough for some peace when you're...
    4 of 5 stars Reviewed January 19, 2015
    Great location; we loved having the back gate for direct access out to Angela Street and the close proximity to the Green Parrot and Blue Heaven - two of our Key West favorites...
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    1 / 25
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+   Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938... View all property information
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    Key West, Florida Keys
    1 / 29
    4.5 of 5 stars (50) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed December 16, 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 stars Reviewed July 24, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    CONDO HAS A VIEW OF THE GULF OCEAN. THE CONDO BALCONY THAT SEAT 6 PEOPLE. THE CONDO HAS A WASHER AND DRYER AND A FULLY EQUIPPED KITHCEN. THE CONDO IS 960 SQ FT. TELEVISION IN LIVING ROOM AND EACH BEDROOM. HAS BEEN NEWLY REMODELED. 1 BLOCK FROM DUVAL ST. WITHIN WALKING DISTANCE TO ALL... View all property information
    Location Information
    Key West, Florida Keys 33040
    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.