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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 14
    4.5 of 5 bubbles (33) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    4.5 of 5 bubbles (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 bubbles (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    5 of 5 bubbles (23) 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
    3 of 5 bubbles Reviewed 1 week ago
    Tidy location near it all unfortunately construction work at the nearby building left us needing ear plugs and surgical masks for the diesel fumes.Owner stated they can't control...
    5 of 5 bubbles Reviewed November 19, 2016
    Deceiving because the outside of the house is very simple, while the inside and backyard are awesome. We had a very enjoyable time using the amenities. The areas were spotless...
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    1 / 32
    4.5 of 5 bubbles (29) 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. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed February 17, 2015
    My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent selection...
    5 of 5 bubbles Reviewed September 2, 2014
    I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
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    1 / 28
    4.5 of 5 bubbles (42) Very good
    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-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 / 39
    5 of 5 bubbles (36) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    May Special $299 a night. 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... 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 / 33
    4.5 of 5 bubbles (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed February 7, 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
    5 of 5 bubbles Reviewed December 12, 2014
    The condo was great. The place was clean, comfortable, and 1/2 block from Duval Street. We were able to walk everywhere we needed to go. There was a porch off of one of the...
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    1 / 33
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
    Location Information
    Key West, Florida Keys 33040
    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
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with... View all property information
    Location Information
    Key West, Florida Keys 33040
    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 / 28
    4.5 of 5 bubbles (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 7, 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    5 of 5 bubbles Reviewed August 6, 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry detergent Traveled...
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    1 / 23
    4.5 of 5 bubbles (21) 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
    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!
    4 of 5 bubbles Reviewed November 20, 2014
    We booked here for one night because of the location. This worked out well for 2 couples - one private bedroom with full bath and separate entrance, one pull-out sofa bed with a...
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    1 / 27
    4.5 of 5 bubbles (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed May 19, 2015
    they advertised this with a hot tub but it was broken when we arrived,and was not repaired until our last day there.told them about it when we arrived and they seemed unaware,and...
    3 of 5 bubbles Reviewed November 11, 2014
    The Osprey Nest accommodation is very comfortable and pleasant. It's a bit of a hike from the action on Duval Street, which is good because it's in a quiet neighborhood, but a...
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    1 / 32
    4.5 of 5 bubbles (39) Very good
    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 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... 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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Part of TROPICAL VILLAGE 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... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with... View all property information
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    Key West, Florida Keys 33040
    1 / 36
    5 of 5 bubbles (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 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 / 28
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 14, 2016
    First time in KW and we LOVED it! The apt is very comfortable and clean, as advertised! Front porch was an added bonus! Could walk to Duval St. 1/2 block away, yet house was...
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    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 / 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 / 27
    4 of 5 bubbles (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 28
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located just steps from Duval St - right off the corner of Amelia and Duval - "Duval Quarters" is the perfect combination of location, luxury and roominess! This 1 bed 1 bath condo is a part of the historic Casa De Luces condominium complex and is now managed by Key West Vacation Rentals, which... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    5 of 5 bubbles (5) 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 December 6, 2016
    We could not have had a better experience of Key West! The Suite Mischief location is a lively spot for watching all the happenings on Duval St. We lived every evening on our...
    5 of 5 bubbles Reviewed August 8, 2016
    Great Location, Great Space, Great amenities, Great balcony, and Great Owner...bed was comfy & bathroom had everything we needed...Thanks again!!
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    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the mid-1900's. Now the inn offers nine beautiful guestrooms and the... View all property information
    Location Information
    Key West, Florida Keys 33040
    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
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 31
    4 of 5 bubbles (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 bubbles 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 bubbles 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 / 30
    4.5 of 5 bubbles (8) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Papa's Hideaway is 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
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    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 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 37
    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
    1 / 24
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed June 28, 2016
    This house had a wonderful location. It was very easy to walk to Duval Street and the Southernmost Point. The beds were comfortable, but the house inside and out needs updating...
    5 of 5 bubbles Reviewed 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...
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    1 / 29
    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 - 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
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    Key West, Florida Keys 33040
    1 / 25
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    With its rich wood flooring and triple windows, this selection is truly fit for a king. Wood and cane furnishings and metal sculpted palm lamps with intricate shell shades make the guest feel welcome and relaxed. Double nightstands and a writer's desk add to the atmosphere without compromising... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 18, 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 bubbles Reviewed May 25, 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
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    1 / 31
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    (Recently updated!) 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... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 5, 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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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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    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
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    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 / 25
    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed August 12, 2016
    The condo was beautifully clean, very spacious and well equipped. The beds and pillows were amazingly comfortable and the maid service was very efficient. The condo's location was...
    4 of 5 bubbles Reviewed July 10, 2016
    Stayed here in June as a family of 4. We were expecting a double and 2 twins but when we arrived the twin room was set up as a double. However, we discovered there was a sofa bed...
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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 / 21
    5 of 5 bubbles (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
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    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 / 31
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    The Hibiscus is located just steps from our heated lagoon pool and adjacent to the Bougainvillea Room. Both Hibiscus and Bouganvillea share a large, semi-private deck, which has access to the front yard and the pool area. This arrangement is perfect for couples traveling together: plenty of common... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary 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 and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 36
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Part of TROPICAL VILLAGE 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... View all property information
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    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 / 24
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    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 and bask by our lagoon-shaped pool surrounded... View all property information
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    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed August 18, 2016
    My boyfriend and I checked in with another couple for a little under a week. The room was clean and was located within 5 miles of Duval Street. We all had a great time!
    4 of 5 bubbles Reviewed May 30, 2016
    We booked this with friends through trip advisor and really enjoyed our 1 night stay, rooms were spacious and comfortable with all mod cons and there was a great pool area.
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    1 / 34
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Duval Hideaway 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. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4 of 5 bubbles (8) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located at Papa's Hideaway is 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... View all property information
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    Key West, Florida Keys
    4 of 5 bubbles Reviewed September 25, 2015
    Clean, quiet, beautiful garden pool, well managed, prompt shuttle, fun to watch the iguanas marching thru and sun bathing in the palm trees. Locations is great, close to Duval on...
    3 of 5 bubbles Reviewed July 30, 2014
    Papa's Hideaway is located on a quiet side street, a block away from Key West's main drag, Duval Street, and a two-block walk from the "Southernmost Point" landmark: a perfect...
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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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    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 and 10'... View all property information
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    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 / 24
    4.5 of 5 bubbles (31) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    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 / 25
    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 - 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
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    Key West, Florida Keys 33040
    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 Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon 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... View all property information
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    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 / 29
    5 of 5 bubbles (1) Excellent
    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 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 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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    Key West Flight and Weather Info
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    73° 64°
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    76° 67°
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    Additional Key West Info

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    • Local time: 10:01 PM (EST)
    • Peak travel: February - 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.