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Leeward Isle Vacation Rentals in Key West

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    37 Reviews
    2 BedroomsSleeps 6Quick View
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    3 BedroomsSleeps 8Quick View
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    16 Reviews
    2 BedroomsSleeps 6Quick View
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    Reviewed 4 weeks ago
    We really enjoyed our time at the Bahama House. The condo was great but our favorite thing was the pool area. Very nice!! Also, we had a problem with the cable and it was taken...
    Reviewed March 15, 2017
    Best location, price, and amenities with simplistic booking,..will definitely return to The Key West Bahama House!
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    36 Reviews
    2 BedroomsSleeps 6Quick View
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    • Internet Access
    • Waterfront
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Reviews
    1 BedroomSleeps 4Quick View
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    • Terrace
    • Wi-Fi
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    • Porch
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    Pet friendly
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    Reviewed March 10, 2017
    This is a lovely place to stay,well furnished, and ideally located right in the heart of the 'action'. However, it is quite expensive, with $25 per day parking charge plus...
    Reviewed February 26, 2017
    5 stars. Great place, everything included, didn't have to bring anything. Old Florida style, best location, in the middle of all the action, balcony lets you view all...
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    26 Reviews
    2 BedroomsSleeps 6Quick View
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    Pet friendly
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    Reviewed February 14, 2017
    Rented this place for my sister's bachelorette party and we had an amazing stay. It really is walking distance to everything and the shared pool was great. It was such a bonus...
    Reviewed February 14, 2017
    Key West Bahama House is located in the perfect spot. Rooms are very nice and clean. The only downside in April of 2016, there was construction at the building behind and...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Reviews
    2 BedroomsSleeps 4Quick View
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    Pet friendly
    Kid friendly
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    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...
    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...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    16 Reviews
    2 BedroomsSleeps 6Quick View
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    Pet friendly
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    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...
    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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    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...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
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    Smoking allowed
    About this property
    Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Reviews
    2 BedroomsSleeps 6Quick View
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    • Internet Access
    • Satellite TV
    • Washer
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    • Sauna
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for...
    Reviewed June 13, 2014
    This vacation rental was huge, nicely decorated, and a great place to stay. The pool, jacuzi, pool house, and courtyard were all amazing - so nice, we spent one full day just...
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    About this property
    Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Beautifully decorated by an interior designer. Custom bathrooms and modern kitchen with stainless appliances. Wireless Internet. This is your home...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 BedroomsSleeps 10Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action! Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining,...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    25 Reviews
    1 BedroomSleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Review
    2 BedroomsSleeps 6Quick View
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    • Washer
    • Satellite TV
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    • Ocean Views
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2016
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Reviews
    2 BedroomsSleeps 6Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 25, 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
    Reviewed November 22, 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 6Quick View
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    • Washer
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    80 Reviews
    2 BedroomsSleeps 5Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Thanks Steve & Sue for allowing us to stay at your place. It accommodated us very well. I especially appreciated the two very nice sleeping areas and the kitchen. Its always...
    Reviewed March 16, 2017
    Thanks Steve and Sue. You made our stay in the Keys so memorable. Your condo was so well stocked and wonderful. We came with 2 children under 3 and they had a blast in the pool...
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    14 Reviews
    5 BedroomsSleeps 16Quick View
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    • Internet Access
    • Patio
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    17 Reviews
    2 BedroomsSleeps 5Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The place was very nice and clean. There were plenty of blankets, pillows, towels, etc. The breeze was fantastic. The balcony was secluded enough that I didn't feel like people...
    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...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** This 2 bed 1 bath unit is located in the quiet and desirable Truman Annex neighborhood. You will be just a short walk from both the liveliness of Duval St and the serenity of the Gulf at Ft Zachary Taylor...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    13 Reviews
    2 BedroomsSleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Reviews
    3 BedroomsSleeps 10Quick View
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    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information. I did not stay in this cottage but our guests had rave reviews and...
    Reviewed March 5, 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
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    About this property
    Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    About this property
    This gorgeous two bedroom, one bathroom property is located in one of the most desirable areas of downtown Key West. With it's lavish walkways, on-site pool and private parking, you will be able to relax and enjoy being in the heart of it all. Take a stroll to Duval Street or to the beach; both...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Review
    2 BedroomsSleeps 5Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 29, 2016
    This location is in Stock Island close to airport, beaches and all the attractions. Exceptionally clean accommodations and was very safe. The pool at the unit was breathtaking...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    25 Reviews
    1 BedroomSleeps 4Quick View
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    • Grill
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    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...
    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...
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    About this property
    Part of the Nightly group unit 4 Flowers 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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 BedroomsSleeps 6Quick View
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    • Air Conditioning
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Reviews
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    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    21 Reviews
    2 BedroomsSleeps 6Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 11, 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    Reviewed October 25, 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute walk away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has a 7 night minimum due to HOA rules :) Welcome to Truman Tranquility - the perfect vacation rental for family & friends alike. The living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private patio, which features...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    25 Reviews
    1 BedroomSleeps 4Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Reviews
    2 BedroomsSleeps 6Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 24, 2016
    Fantastic. No other word describes it better. The view, the amenities, the layout of the condo...all fantastic. Owner is a very nice lady too. Very easy to deal with. Will...
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    16 Reviews
    2 BedroomsSleeps 6Quick View
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    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 6, 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed July 14, 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    27 Reviews
    StudioSleeps 2Quick View
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    • Internet Access
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    Hibiscus Hideaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St. Welcome to the perfectly located and affordable apt Hibiscus Hideaway. You will not find a better spot to spend your sunny days and exciting...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Reviews
    2 BedroomsSleeps 6Quick View
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    • Terrace
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2017
    Our location was the Sunrise Suite located one mile from the Airport. The place was clean and comfortable. Every time we needed a ride to Old Town, Steve always deliver and on...
    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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    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Reviews
    StudioSleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Terrace
    • Satellite TV
    • Balcony
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    12 Reviews
    2 BedroomsSleeps 6Quick View
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    • Internet Access
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed June 5, 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Reviews
    StudioSleeps 4Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    Reviewed March 23, 2016
    My Daughter and I stayed in Ibis Suite. We Loved the location and the secluded quietness of our suite. The Cuban coffee shop, the Sandwich shop, the Grocery store, the Trolley...
    Reviewed June 2, 2015
    My friends and I stayed at Ibis this past January (all in our mid 20's). I thought I reviewed this property then, but apparently I did not. It was our first trip to Key West and...
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    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    23 Reviews
    1 BedroomSleeps 4Quick View
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Internet Access
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 1, 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space...
    Reviewed May 30, 2015
    As good as the unit was and it really was its the people behind the organisation that make the difference ! I had stuffed up my original booking by 4 weeks, hey I'm old, it's...
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    About this property
    With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. 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! Abaco Suite, is a bi-level suite with a very spacious...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    15 Reviews
    2 BedroomsSleeps 6Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Great location, comfortable beds, would stay again. A couple of minor things around the house could use repair, but was not important to us.
    Reviewed August 9, 2016
    My friends and I went on a wonderful 4 day trip to Key West. We stayed at the Du Pont house which was perfect for 5 people as there were 2 bedrooms and one pull out couch. The...
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    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    StudioSleeps 2Quick View
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    • Satellite TV
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    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    Reviewed November 11, 2014
    This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom...
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    About this property
    Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    16 Reviews
    2 BedroomsSleeps 6Quick View
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    • Internet Access
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    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 King pillow top bed upstairs, another...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    23 Reviews
    2 BedroomsSleeps 6Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 6Quick View
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    • Parking
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    • Balcony
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Reviews
    2 BedroomsSleeps 6Quick View
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    • Satellite TV
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2016
    Our only wish is for additional air conditioning units in living area and bathroom. Everything else was wonderful
    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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    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...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Review
    2 BedroomsSleeps 6Quick View
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    Pet friendly
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    Reviewed July 23, 2016
    Other than a toilet that numerous times erupted like s volcano the place was great, perfect location, daily towel service, would go definitely go back
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    About this property
    This 2 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 and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be better!...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    32 Reviews
    3 BedroomsSleeps 6Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2016
    Beautiful home. We hated to leave. The property is well kept and the accommodations were beyond our expectations. We had our own private pool to lounge in and enjoy after...
    Reviewed November 11, 2014
    The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
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    About this property
    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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