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Wheelchair Accessible Holiday Rentals in Key West, FL

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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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    1 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    5 of 5 stars (34) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
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    • Pet-friendly
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    • x
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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 4 weeks ago
    This rental has all you could want. The kitchen has anything you could possibly want in the way of preparing food. Just run to Publix and get some food. Condo already has plenty...
    5 of 5 stars Reviewed 22 December 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 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Incredible resort during the "peakest" of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Satellite TV
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    • DVD Player
    • Washer
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 May 2016
    When we arrived at the condo there was construction going on around it and it was a little confusing. However, when we got in the room it was breath taking !! The view is...
    5 of 5 stars Reviewed 28 December 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
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    1 / 32
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 24 January 2016
    The property was great. A few issues with C120. The fridge had rust. The TV in the living room was computer monitor sized. We like to catch a game now and then and it was like...
    5 of 5 stars Reviewed 5 January 2016
    The onsite property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • Hot Tub
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    1 bedroom with king bed. Living room with pull out sofa bed. 1 bath with jacuzzi tub and shower. Washer and dryer in unit. Balconies off of bedroom and living room with marina view. Stainless steel appliances. The Galleon has a heated pool with hot tub. A small private beach. Poolside tiki bar... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 28
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Fairwinds at the Foundry is a gorgeous 3 story end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This light and airy end unit is immaculate! Classic and beautiful coastal two bedroom, two and a half bath 3 story townhouse. Enter... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 17 August 2015
    Condo was perfect for our family of four, private baths for us and for the kids, nice bright living area, and a nice compact kitchen. Also included a half bath and laundry. Less...
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Outdoor Dining Area
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    • x
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    • x
    About this property
    THE MARTHA SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Air Conditioning
    • Terrace
    • Satellite TV
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    THE BESS SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Recently... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 23 October 2015
    This condo is stunning and very clean. We were close to all the action to Duval, which was fantastic. We walked all day long and left the car rental parked unless we needed to...
    5 of 5 stars Reviewed 11 September 2015
    The suite is clean, comfortable, spacious and perfectly located in the middle of Old Town Key West close to everything. The rental agency was super helpful (we were 24 hours late...
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    1 / 30
    5 of 5 stars (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Private Outdoor...
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 July 2015
    The home was just lovely. Very clean, nicely furnished and quite comfortable. The pool was so refreshing and the courtyard was tropical with beautiful outdoor furniture. The...
    5 of 5 stars Reviewed 5 July 2015
    This house is in the perfect location with all of the need amenities! Just a wonderful place to stay and a great time! Enjoy ....you won't regret it!
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    3 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Hot Tub
    • Children's Pool
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    I rent starting the first of the month till the end of the month, or longer. Once you pay the monthly rate, you have the option of using the property for as many, or as few days as you would like during that calendar month. You have total flexibility with your arrival dates and departure dates, as... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    THE MARGARET SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 3 June 2015
    The location was great...less than a block off Duval. The unit was very clean and decorated very nicely. It would have been nice if there had been some staples in the kitchen such...
    5 of 5 stars Reviewed 24 March 2015
    We just returned from a fabulous stay at Truman Suites - Margaret. A few comments: (1) The location cannot be beat. Within walking distance of all there is to see in downtown...
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    1 / 31
    6 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • x
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    • x
    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES consist of four Luxury Vacation Rentals that can be rented together or separately. LOCATED ONE HALF BLOCK FROM DUVAL STREET, this location is perfect for a multi generation family... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New owners invite you to enjoy this vacation rental aptly named "Seas the Day!" This newly updated 2 bedroom 1 bath first floor condo is located in the Shipyard section of the Truman Annex. If you are looking for a great location central to all that Key West has to offer, look no further! Park... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 May 2016
    We had a very enjoyable week stay in Key West. Seas The Day is a very nice condo in the Shipyard area of Truman Annex on the western end of Key West. The condo was very clean...
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    1 / 14
    4 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    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...
    4 of 5 stars Reviewed 28 May 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
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    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 29 January 2016
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service to...
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Porch
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    THE HARRY SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 6 July 2015
    The condo was absolutely perfect and a prime location. When we entered it was like waking directly into the pictures posted, absolutely perfect. It was conveniently located a half...
    5 of 5 stars Reviewed 5 July 2015
    We considered a lot of options when planning our week in Key West. The rental company was flexible with our arrival time, easily reachable by email and text, and very responsive...
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    1 / 31
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Outdoor...
    • Satellite TV
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 29 December 2015
    Potter's Cottage is even lovelier than the pictures show it to be. My husband and I and our two adult children met here to enjoy Christmas in Key West. The cottage location is...
    5 of 5 stars Reviewed 12 August 2015
    great location. one can walk to almost every destination. clean. well equipped. great a/c. quaint and quirky--in a good way. would absolutely stay there again. concierge is a...
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    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 5 July 2015
    The Solaris cottage was down a quaint little lane that was smack dab in the middle of the historic district of Key West. We were in short biking distance of every place we wanted...
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    1 / 32
    5 of 5 stars (10) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    “Southard Comfort” is true Island living in downtown Historic Old Town Key West Two story, 3 bedroom, 2.5 bath plus outdoor shower. Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 19 February 2016
    Read no further: You would be silly not to book Southard Comfort for your Key West vacation. It lacks nothing. The physical home and the home's location are superb. I cannot...
    5 of 5 stars Reviewed 27 December 2015
    This lovely cottage on Southard street was just perfect for our Christmas holiday vacation. The pool was a welcome treat after spending the day walking on Duval street. The...
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    1 / 24
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    This place was truly amazing...hidden where you would never expect it. Loved the high end finishes, all your needs for the kitchen, the privacy for each guest, the convenience of...
    5 of 5 stars Reviewed 8 April 2016
    We needed to get away from Midwestern winter and having been to key west multiple times were excited to find this suite. It was pet friendly and the suite has everything one...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 5 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    • x
    About this property
    MONTHLY RENTAL ONLY <BR><BR>Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Grill
    • Central Heating
    • Balcony
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    • Child-friendly
    • x
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    • x
    About this property
    Plan your Thanksgiving getaway at this spacious residential-style 2-bedroom/2-bath villa features private balcony, Master suite with king bed and connecting master bathroom and spa tub; Guest queen bedroom & guest bathroom; Fully equipped kitchen with separate dining ares; Living room with sofa... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
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    • x
    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The Garden at Poinciana Place is a cozy and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Waterfront
    • Sauna
    • Washer
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    About this property
    The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 March 2016
    The condo was great, had all the amenities! Perfect location, right across from the beach, beautiful view! Plus it wasn't far from downtown.
    4 of 5 stars Reviewed 19 July 2015
    Myself, my husband, my sister and brother-in-law had visited Key West on a cruise and wanted to return for a week vacation. I rented this condo because of it's location to a...
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    30 DAY MINIMUM RENTAL This stately home, located in the center of historic downtown Key West, offers up a perfect combination of location, charm, space and privacy. The entrance hallway and staircase are bright and airy, decorated in cool blue tones and exposed Dade county pine. The downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040