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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 14
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 stars (22) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 8, 2016
    This is a roomy two bedroom apartment, very clean and nicely decorated. You couldn't ask for a better location to all things around downtown Key West - one block off of Duval...
    5 of 5 stars Reviewed February 3, 2016
    This is a beautiful unit in a perfect location. There are 2 bedrooms with very comfortable beds, and two bathrooms. One bathroom is full size and the other is rather small, but...
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    1 / 14
    4.5 of 5 stars (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 stars 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 stars 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 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
    4 of 5 stars 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...
    5 of 5 stars Reviewed March 5, 2016
    Condo is a $25 cab ride including tip (2016 prices) from Duval Street area where most bars/restaurants/shopping/tourist sites are located. However all cab companies were familiar...
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    1 / 13
    5 of 5 stars (3) 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 stars Reviewed 2 weeks ago
    Tom from Duval Balcony was wonderful. He communicated with me to confirm my visit and then to make arrangements to meet when it was time to check in. When we arrived he...
    5 of 5 stars Reviewed October 22, 2015
    Being a Florida local, I travel to Key West quite often for the past 13 years and have never had a better and more pleasant stay than at the Duval Balcony. The owner was waiting...
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    1 / 22
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 5, 2015
    My Husband, I and my sister spent 6 days in Key West. This was a home like condo to stay in. It had a kitchen,dining room and living room on the main level with a bathroom(all one...
    4 of 5 stars Reviewed April 8, 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    1 / 23
    5 of 5 stars (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 stars 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...
    5 of 5 stars Reviewed January 18, 2016
    My husband and I stayed with friends at this beautiful home (Oasis lives up to its name). Our friends who we were traveling with had been to Key West many times, but this was our...
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 23, 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group had...
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    1 / 12
    4.5 of 5 stars (12) 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 stars Reviewed 1 week ago
    We LOVED this condo for our stay in Key West. The condo was very clean, spacious, absolutely adorable, and most importantly affordable! It was nice to have access to a pool and...
    5 of 5 stars Reviewed June 9, 2016
    I stayed here for 2 days this summer. My 2 adult son's, daughter in law and grand baby. Overall quiet area, very easy to get around, didn't have a chance to swim in the pool. We...
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 stars Reviewed October 25, 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars 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 stars 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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    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
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    Key West, Florida Keys 33040
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Tastefully furnished private studio with ensuite bath in quiet, coveted residential neighborhood in Old Town Key West (where you want to be). Bath has granite countertops. Your own private entry. King size bed. No kitchen, but studio is equipped with microwave and two-door refrigerator. (There's... View all property information
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    Key West, Florida Keys 33040
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Live the Key West boat lifestyle. Cocktails on the aft. deck. Sunning topside before catching the glorious world famous sunset. 4 ensuite staterooms. Master cabin has king be fans the 3 others each equipped with 2 twins. Located in the heart of downtown Key West you can walk to all attractions,... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... 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
    Welcome to our unit at Coconut Beach Resort Come stay at a private tropical paradise, completely renovated the last few years yet reminiscent of days gone by, sitting quietly and serenely right on the ocean on the Atlantic side of Key West. Here you will find a blend of old island architecture,... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed October 14, 2015
    Location, while good very close to Airport which was noisy at times. Bedrooms good size. However, plastic mattress protectors were uncomfortably hot, unnecessary and had to be...
    5 of 5 stars Reviewed June 26, 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
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    1 / 38
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half... 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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    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
    1 / 39
    5 of 5 stars (34) 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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    This rental has all you could want. The kitchen has anything you could possibly want in the way of preparing food. Just run to Publix and get some food. Condo already has plenty...
    5 of 5 stars Reviewed December 21, 2015
    The owner of this condo. goes out of her way to make your vacation enjoyable. She has beach chairs, beCh towels, sun screen, beach umbrellas, etc etc. available for you to use...
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Just one-half block from famous Duval Street, this turn of the century cigar makers cottage lies in the center of Old Town. Just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This KEY WEST HOUSE is just steps from restaurants, night life,... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Allinclusivecharter provides the perfect getaway on your own private crewed luxury motor yacht in the Florida Keys area. Being the only guests on our board, you are treated like royalty. Do what you really want, when you want. Your voyage is personalized and is a customized vacation tailored to you... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 14, 2013
    Fabulous place but we did not realize that we would be overlookeing a major highway, whose traffic is worse due to contstruction on the other side of the island. We'd stay there...
    5 of 5 stars Reviewed March 5, 2013
    This was the best. My wife could not make the getaway. Ya, me alone. It was a last minute decision. The condo was clean. 2 large bedrooms & bathrooms with a fold out couch...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    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
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    Key West, Florida Keys 33040
    5 of 5 stars 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 stars 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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    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with... View all property information
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    Key West, Florida Keys 33040
    1 / 5
    3.5 of 5 stars (2) Average
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    Live in luxury poolside in a beautifully furnished studio (private room and full bath) apartment, situated in a quiet, coveted residential Key West neighborhood. Walk right outside your door into an enchanting, very nicely landscaped pool/deck area for your enjoyment. You'll be strategically... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 10, 2016
    From the moment we arrived into the tropical lush forrest, which enclosed the pool and property, we knew we were in paradise! We were pleasantly greeted by Chuck, the owner & his...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***PRICE AND AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. CHECK IN DATES FOR THIS RESORT ARE FRI/SAT/SUN*** Situated on the Atlantic Ocean, the property captures Key West style with modern convenience. Conveniently located near Key West Int'l airport and only a short distance to beaches,... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed October 31, 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    1 / 38
    4.5 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 stars 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 stars 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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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old Town" Key West. Walking distance to Ft Zachary Taylor State Park & Beach, Blue Heaven, The Earnest Hemingway House, and much more! Free WiFi, cable TV, & daily housekeeping... View all property information
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    Key West, Florida Keys 33040
    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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 4, 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
    5 of 5 stars Reviewed December 15, 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
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    1 / 99
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 stars 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...
    5 of 5 stars Reviewed July 20, 2015
    Great place to sleep-we spent most of the time touring-courtyard was great for meeting new friends-place was very clean and plenty of space for 3 couples-location was very...
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    1 / 26
    5 of 5 stars (1) Excellent
    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
    5 of 5 stars Reviewed March 15, 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it was...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Tropical Breeze is decorated in a tropical motif, with a cozy palm frond matelassé. There are wood and wicker furnishings throughout. Traditional Key West shutters allow the floral scents and chirping of birds to drift through the room. The door opens onto our second story landing where you are... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed November 1, 2012
    Really enjoyed the condo and the fact it was across from the ocean. It was only minutes away from Duval Street where we spent the majority of our time. Would stay here again.
    5 of 5 stars Reviewed August 29, 2012
    My husband and I spent 10 days here in August and thoroughly enjoyed our time. The view from our balcony was great and was one of the reasons why we picked the spot. The...
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    1 / 24
    4.5 of 5 stars (19) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed August 18, 2015
    Starr Suites was located in a great place close to everything. The Suites need a little work, they are clean but they need some items repaired and replaced. The Hot tub is worn...
    5 of 5 stars Reviewed July 14, 2015
    We stayed in the Starr suite of the Abbey Road complex. It was well stocked, with all the amenities you might need. It was updated recently I believe so everything felt new 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 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 / 34
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    (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 stars 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 / 22
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 13, 2016
    The house was really nice. The owner and the property manager (NOT Tim from Historic Hideaways) were very helpful when we couldn't figure out the TVs and ALL the remotes!! Lol I...
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (43) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
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    Key West, Florida Keys
    5 of 5 stars Reviewed June 16, 2016
    This place is a slice of heaven. Adorable from the front and even better in the back. Covered porch and pool in the backyard along with a grill and outdoor shower. Three houses...
    5 of 5 stars Reviewed October 24, 2015
    We stayed for a week, and absolutely loved this little cottage, though we really only used the back half of it. The house is steps away from the side gate of Hemingway House and...
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    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.