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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
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | 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 (12) 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 / 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 / 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 1 week 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 / 12
    4.5 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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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 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...
    3 of 5 stars Reviewed May 31, 2016
    This condo was very large and we could spread out as a family, which is great when you have two teenagers. The beach in front of complex is tiny and not really usable for...
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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 / 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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    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 / 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
    Location Information
    Key West, Florida Keys 33040
    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
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
    • Ocean Views
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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
    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, 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
    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 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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    1 / 27
    4 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    TRUMAN'S HIDEAWAY: Lovely condo in the exclusive Harbour Place condominium complex in Truman Annex. Spacious living/dining room area, fully equipped kitchen, Master bedroom with king bed, guest bedroom with bunk bed (1 twin on top, 1 full on the bottom, 1 twin trundle on the bottom) private deck... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 12, 2013
    The house is old and vert worn. It needs upgraded paint and bedding plus nicer sheets and bath towels. The kitchen was fairly well equipped and adequate but could use updated pans...
    3 of 5 stars Reviewed December 12, 2013
    This property has a great location near Mallory Square and many attractions. Truman's Little White House is in your backyard! It needs a few updates and clean up in our opinion...
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    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Mountain Views
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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
    1 / 23
    4.5 of 5 stars (32) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    FINN KEY: 2 bedroom 1 bath downstairs condo in The Shipyard section of Truman Annex, one of the most popular spots in Old Town Key West. Remodeled with attention to detail, the kitchen sparkles with top of the line appliances, cabinetry and every amenity needed. Opens to a sunny living room... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2016
    Lovely condo,great location, have stayed at Truman many times. Condo is clean and comfortable, neighbors upstairs must live here full time, they walk a little heavy but I suppose...
    4 of 5 stars Reviewed May 12, 2015
    Registration on line was easy, good communication from rental agency. Agency is off site so key pickup and drop off is not as convenient as with Compass Realty, a different rental...
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    1 / 20
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room. Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014. There is a community pool area to... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 4, 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
    4 of 5 stars Reviewed December 5, 2013
    Very nice 2 bedroom 2 1/2 baths located in an excellent location. Walk right down to Duvall Street. Located at the quite end of Duvall. Great accomdations but a bit pricey.
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    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 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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    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 / 27
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    LINGER LONGER: 2 bedroom 1.5 bath townhome in Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on the 2nd floor. Downstairs is an open floor plan with kitchen/dining/living room and half bath. French doors... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 18, 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    4 of 5 stars Reviewed April 27, 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived at...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    SUNSET CELEBRATION: Coming Soon! 2 bedroom 1 bath Shipyard condo located in Truman Annex. Currently undergoing renovation to include new floors, fresh paint, all new furnishings, artwork, linens and towels. Be the first to stay in this totally updated vacation home. Master bedroom will have queen... 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 / 32
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    KEY WEST CROWN JEWEL: 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space. WIFI, flat-screen plasma television with Bose surround sound system in the living room, as well as TV/VCR/DVD/CD players in each bedroom. Large, fully-equipped modern kitchen with granite... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 26, 2014
    We had the great honor of staying in this unit for a week in March. Our teenage daughter had her own bedroom and bath, which was wonderful. The entire condo is clean, well...
    5 of 5 stars Reviewed March 14, 2012
    Again thanks to Gale she does a great job and is easy to work with. Have already booked The Crown Jewel for next year and plan to do so for years to come. Thanks Mitch and...
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    1 / 22
    4 of 5 stars (44) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in the heart of Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room but appreciate the amenities of a vacation rental. Sunny and bright this cottage has... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 21, 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
    5 of 5 stars Reviewed October 26, 2014
    We had a wonderful time staying at Osprey and will reserve this cute little place every time we go to Key West. The location on Olivia St is ideal for getting to all the action...
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    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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
    1 / 39
    4.5 of 5 stars (29) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and sunshine with ocean breezes wafting by. Condo offers street view; complex offers ocean... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 29, 2014
    With a short walk to the beaches, the awesome pool and hot tub, and quick drive to Duvall Street, this was the perfect place to stay! Our condo was so clean and spacious and we...
    5 of 5 stars Reviewed April 12, 2014
    We love the location next to the beach. The pool and hot tub were clean and a perfect temp. The rental was very clean and well equipped. We bought more toilet paper and could...
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    1 / 24
    4.5 of 5 stars (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master bedroom has a private balcony.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 6, 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
    5 of 5 stars Reviewed February 26, 2014
    Loved Duval Breeze! The house was bigger than the pictures depicted and it was so comfortable. Having not only towels and linens available but also basics like toilet paper and...
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    1 / 27
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    CITY CAY: City Cay is our 1-bedroom 1-bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style. Stay connected in the living room with high-end electronics including HDTV, WIFI and an over-the-top stereo system. Relax on the covered back balcony... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 4, 2015
    We stayed at City Cay over the Thanksgiving holiday. The condo is on the second floor of a building in the Shipyard Annex of Truman's Annex complex. We had wanted to stay in...
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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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    • ?
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    • x
    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
    Location Information
    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 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 / 27
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 13, 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
    5 of 5 stars Reviewed April 3, 2015
    We had an incredible time at the Bahama House in Key West. We were in town for my sister's wedding and our party included my parents, my wife and two young children and my sister...
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    1 / 22
    4.5 of 5 stars (83) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    BAHAMA DREAMING: One Of At Home In Key West's Most Popular Rentals! Bahama Dreaming is a traditional 3-bedroom Conch cottage located just steps from Duval Street. With it's fantastic location and amenities this home offers it all. The main level has 2 bedrooms, one containing a comfy queen size... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 4 weeks ago
    We have just returned from our yearly girls trip to Key West. We are a group of 6 women in our late 50's (60's) who visit every year in June for a week of fun. First, let ,e...
    4 of 5 stars Reviewed April 18, 2016
    We enjoyed our stay at Bahama Dreaming. The house was very clean and comfortable, well stocked with kitchen items as well as plenty of beach towels. The pool was small but clean...
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    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    About this property
    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 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors that... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 29, 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    1 / 26
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a prestigious gated community in Old Town. Surrounded by tropical greenery in a beautiful quiet gated community 2 blocks from Duval Street and Mallory... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Easy Livin' - The name says it all! This lovely private home with pool in a secluded cul-de-sac in Truman Annex, a pristine gated community located in historic Old Town Key West is walking distance of anything you will want to do during your visit. The formal entrance of this vacation rental... 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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    About this property
    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
    Location Information
    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 / 17
    5 of 5 stars (22) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Forget that "been there, done that" hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and "Sunset Celebration". The original local artwork throughout... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 12, 2015
    I arrived on a rainy, nasty day in Key West. It was pouring. Duval Street was flooding. The temperature was in the 50s. But I was in Key West, so it couldn't be all bad. It...
    5 of 5 stars Reviewed December 10, 2013
    We have been traveling to Key West 1-2 times a year for about 15 years and have stayed everywhere from the most economical to the high end resorts and will confidently say this...
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    1 / 14
    4.5 of 5 stars (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Newly renovated apt with all new appliances, granite counter tops & plank flooring. A large balcony to enjoy your morning coffee while catching an ocean view and watching the iguanas playing in the grass and trees.My apt is close to the Key West airport & all the amenities and attractions that Ley... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
    • ?
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    • x
    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 3, 2013
    I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
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    1 / 29
    4.5 of 5 stars (11) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport. Fully equipped kitchen, HDTVs, WIFI and off-street parking for... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed April 10, 2014
    Rent this condo if you are looking for a place out of the fray but nonetheless close. It is 10 - 15 minutes to Duval Street, and very bikeable. Stock Island eateries (Roostica...
    4 of 5 stars Reviewed October 10, 2013
    A group of 7 of us stayed here for 4 days and it was a very nice time. There was a slight shortage of towels but there was a washer and dryer that was fast and easy to use in the...
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    1 / 24
    4 of 5 stars (28) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    PAPAYA PLACE: 2 bedroom 2 bath condo at 1800 Atlantic Blvd. with garden view overlooking the nature preserve. Master bedroom with new king bed and bathroom ensuite; twin beds in guest bedroom with full bath across the hall. WIFI, unlimited long distance calls,3 flatscreen TVs and expanded cable... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 8, 2016
    My wife and I have been staying at Papaya place for years and it just gets better! The beautiful colors and homey touches are our favorite. It is always immaculate when we arrive...
    5 of 5 stars Reviewed May 26, 2016
    This very pretty and comfortable condo was in a great location - access to the beach, very close to the airport and a five minute cheap cab to Duval Street. The condo is very...
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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.