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Apartments in Key West, FL

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    Travellers to Key West are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 14
    4.5 of 5 bubbles (31) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 14
    5 of 5 bubbles (22) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 bubbles (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 bubbles Reviewed 8 February 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 bubbles Reviewed 4 February 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 / 15
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • DVD Player
    • Porch
    • Balcony
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    • Satellite TV
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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 bubbles Reviewed 10 March 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 bubbles Reviewed 19 March 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 / 13
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Balcony
    • Satellite TV
    • Patio
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 August 2016
    Great Location, Great Space, Great amenities, Great balcony, and Great Owner...bed was comfy & bathroom had everything we needed...Thanks again!!
    5 of 5 bubbles Reviewed 11 July 2016
    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...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles Reviewed 14 July 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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    1 / 32
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 3 weeks ago
    House was very clean and the owner was very helpful and responsive. I would definitely stay again and would highly recommend it to anyone going to key West !
    5 of 5 bubbles Reviewed 31 August 2016
    We loved every part of this rental. It was clean, not cluttered, great location, well-equipped, quiet and very comfortable. The pool was very nice and the community friendly...
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    1 / 12
    4.5 of 5 bubbles (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Balcony
    • Internet Access
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    • Outdoor Dining Area
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 25 October 2016
    Really enjoyed my stayed, I Will definitely will stay hear again, everything was just as expected, location was great, owner was fantastic and very helpful, apartment was very...
    4 of 5 bubbles Reviewed 18 August 2016
    Two bedroom, two bathroom condo suite with patio, across the street from the water. Each bathroom is connected to a bedroom, with the master bedroom having private access, of...
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Satellite TV
    • Ocean Views
    • DVD Player
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 23
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 bubbles Reviewed 26 January 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 bubbles Reviewed 18 January 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 / 99
    4 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Grill
    • Porch
    • Air Conditioning
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 10 November 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 bubbles Reviewed 21 July 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 / 14
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 bubbles Reviewed 30 December 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 / 6
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 2 weeks ago
    This place was very nice and cozy just steps away from duval . Perfect for a quiet get away for you and/or your spouse . I've stayed many places and this one was just right for...
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    1 / 14
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 bubbles Reviewed 16 April 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 bubbles Reviewed 5 March 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 / 7
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 bubbles Reviewed 23 February 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 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Terrace
    • Central Heating
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
    • Ocean Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 25 October 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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    1 / 6
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Balcony
    • Air Conditioning
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    • Porch
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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 bubbles Reviewed 19 September 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 bubbles Reviewed 25 May 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
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    1 / 33
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 18 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    5 of 5 bubbles Reviewed 25 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back in...
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    1 / 51
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Sauna
    • Private Outdoor...
    • Hot Tub
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 16 July 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 the...
    5 of 5 bubbles Reviewed 14 June 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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    1 / 21
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and free laundry. Take it out for a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 2 days ago
    My family and friends stayed on Tim's catamaran yacht for two nights in October. We were six adults, two teenagers, and two toddlers. The vessel had plenty of space to...
    5 of 5 bubbles Reviewed 4 days ago
    We had a family group of 7 (all adults) visiting Key West from Australia. When searching for somewhere that would accommodate a group of this size I came across this fantastic...
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    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
    • Washer
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
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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 bubbles Reviewed 10 February 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 bubbles Reviewed 26 October 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 / 30
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Patio
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    • Grill
    • Housekeeping...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 bubbles Reviewed 1 week ago
    This was our second time renting a this wonderful Condo. Owner is always updating his condo and likes feedback from renters.Plenty of pans, glasses and dishes but only has 4...
    5 of 5 bubbles Reviewed 4 January 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...
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    1 / 17
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Ocean Views
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    • Pet-friendly
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    • Smoking allowed
    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 29 September 2016
    Trip of a lifetime. John and Dania were great. We sailed from key west, spent a few days in cuba and went all over the place...John and Dania were great tour guides. Finished the...
    5 of 5 bubbles Reviewed 13 September 2016
    Calypso, Captain John, and Mate Dania, were wonderful! The trip over to Marina Hemingway was fun, as was the stay at the marina. The catamaran was well stocked, having...
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 29
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Outdoor Dining Area
    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 18 September 2016
    We stayed at the Potter's Cottage and thoroughly enjoyed our experience. The property was in fantastic condition - fully modern with generally high quality finishes. One full...
    5 of 5 bubbles Reviewed 27 July 2016
    We recently stayed at The Potter's Cottage for a week in July. The cottage itself is lovely and quaint. It has been fully remodeled and was very clean. The rental included bed...
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    1 / 20
    3 of 5 bubbles (1) Average
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 12 August 2016
    The Room was clean and the kitchen a plus, however, it was very tight for 2 people. The only place to hang clothing is on the back of the shower door which hits the bed when...
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    1 / 24
    4.5 of 5 bubbles (25) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • ?
    About this property
    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 bubbles Reviewed 13 April 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 bubbles Reviewed 3 April 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 / 23
    4.5 of 5 bubbles (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 bubbles Reviewed 19 May 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 bubbles Reviewed 28 April 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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    1 / 24
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • ?
    About this property
    CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off-street. Built for entertaining from the wide open floor plan that encompasses the spacious living room and grand kitchen to the magnificent pool. Master bedroom with bath ensuite shares first floor with... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 6 May 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard, spacious...
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    1 / 27
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 18 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    1 / 24
    4.5 of 5 bubbles (25) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    LAVENDER JUNGLE: 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex. Renovated kitchen and upgraded bathroom. Large brick patio and grill. Master bedroom with queen bed and guest bedroom with 2 twins on either side of the full bathroom. Well-equipped kitchen. Truman Annex is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 11 August 2016
    I cannot stress to you enough how good of a location this condo is in! It's a 15 min walk or less from Duvall St, Mallory Square and Ft. Zachary Taylor. I'm so glad we chose this...
    5 of 5 bubbles Reviewed 9 August 2015
    My family and I stayed at the Lavender Jungle condo and totally enjoyed our time there. The location was perfect..convenient to the beach and Duval St. The property was very...
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    1 / 23
    4.5 of 5 bubbles (27) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps... View all property information
    Location Information
    Key West, Florida Keys 33045
    5 of 5 bubbles Reviewed 29 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
    5 of 5 bubbles Reviewed 7 April 2015
    Great unit, very well maintained. Repeat customer and would recommend this to anyone! I would only add chairs to the front porch.
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    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    5 of 5 bubbles (36) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    May Special $299 a night. This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    We were so thrilled to stay in this vacation rental, My mom is in a wheelchair full time and there was enough room for her to get around, the bathroom was perfect for her. My 2...
    5 of 5 bubbles Reviewed 6 August 2016
    Best aspect: owner Kathy W. communicated as stay got closer. She even asked how we were doing the day of travel and invited us to call her with any concerns or questions. We...
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    1 / 23
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    SUNDOWN REFUGE: Brilliant sunshine and magnificent sunsets in the Harbour Place condo complex in Truman Annex. Overlook Florida Bay in one direction and Truman's Little White House in the other direction from the privacy of deck. Fully furnished with the necessities of home and anything you'll... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 27 November 2014
    We stayed here with family in Nov while attending a family wedding. The condo was a characterful, quirky place which had every facility required for a wonderful stay. It felt as...
    5 of 5 bubbles Reviewed 2 March 2013
    Location was great, easy walk to Mallory Square, Duval Street, Beach. Rent bikes, easy to ride to just about anyplace safe and quickly.
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 / 23
    4.5 of 5 bubbles (29) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Grill
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    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 bubbles Reviewed 30 July 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 bubbles Reviewed 13 April 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 / 15
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Terrace
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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 bubbles 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 bubbles 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 / 32
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool...
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    • Satellite TV
    • Waterfront
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 February 2016
    The boat is big and very comfortable for my family (5) very luxurious to the smallest details, has a jacuzzi on the top and kajacs to navigate the beautiful sea. It was awesome...
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    1 / 24
    4.5 of 5 bubbles (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Satellite TV
    • Terrace
    • Private Outdoor...
    • DVD Player
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    KEY WEST CASA: One of only a few 3 bedroom 2 bath condos in the Shipyard complex in Truman Annex. Enter the fully stocked kitchen to the living room to the French doors that open onto the back porch. The downstairs bedroom is just to your left and offers 2 twin beds next to the bathroom. Upstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 12 June 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
    4 of 5 bubbles Reviewed 9 April 2014
    Check-in & out was excellent, no problem, Great! It was so nice to feel like you were home and not stuffed in a little one room. The location is perfect, you are close to...
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    1 / 24
    4.5 of 5 bubbles (35) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen TVs, stereo,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 23 January 2014
    We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.
    5 of 5 bubbles Reviewed 20 November 2013
    We just love this little get away home that we get to stay at when in Key West. The new owners have done a nice job of re-modeling and the Leeward Isle is so comfortable.
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    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is an amazing summer rental. Available during June and part of July only for either long weekends or by the week. Stunning location within the old town of Key West, over two levels, full kitchen, bbq, 2 bedrooms, shared pool. (Only between 4 houses) It just doesn't get better than this This... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    5 of 5 bubbles (12) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Private Outdoor...
    • Satellite TV
    • Grill
    • Air Conditioning
    • Porch
    Suitability
    • 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 bubbles Reviewed 6 August 2016
    This was the perfect place for my friends and I to spend vacation. House is super clean. Very private. Close enough to walk to duval but far away from the craziness when you go...
    5 of 5 bubbles Reviewed 3 August 2016
    This home was perfect!! It had the most beautiful front porch, with a swing and rocking chairs! Inside the decor was so lovely. The living room was comfortable, and perfect for...
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    1 / 23
    4.5 of 5 bubbles (36) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • DVD Player
    • Terrace
    • Satellite TV
    • Balcony
    • Private Outdoor...
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with laundry closet. Guest bedroom on the main level with 2 twin beds... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 18 January 2016
    This place is very nice and has all the convenience's of home. Located one block off of Duval street so you can walk Duval, drink and not have to drive home. The weather was...
    5 of 5 bubbles Reviewed 15 May 2015
    Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.
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    Holiday Rental Accommodation on Key West

    The diversity of the holiday rental accommodation available on Key West means that there is something available to suit every budget and surely all tastes. From cottages and modest condos, to villas and townhouses, to penthouses and country estates, Key West has it all, meaning that your holiday in Key West can be as free of restriction as possible, at a price you can afford. If you want the freedom to explore Key West at a time and in a manner of your choosing, selecting the holiday rental best suited to your individual requirements is the way to achieve your goal.

    Water sports in Key West

    The weather and geography of Key West make it an ideal location for a great many different types of water sports. Fishermen of all disciplines can choose from the art of fly fishing for tarpon, to deep sea fishing expeditions from a boat and most options in between. Those simply interested in being out on the water can go pleasure cruising on a charter boat, perhaps to view the dolphins and other marine life, hire a kayak and meander through the waterways at their own pace, or even jump on a jet ski and enjoy some high speed thrills. Scuba divers can admire the natural coral reefs or explore the wrecks in the area, some of which were deliberately sunk to form artificial reefs.

    Popular attractions in Key West

    The beaches of Key West are both numerous and beautiful but a visit to the Fort Zachary Taylor State Park allows you to combine your beach relaxation and activities with an inexpensive tour of the fort, or perhaps a casual stroll along one of the nature trails. Art lovers will find a great many galleries of interest in Key West, with the majority local to the popular Duval Street part of town. Key West Golf Club is not only about allowing golf lovers to practise their swing, it also has a popular restaurant and bar, which could perhaps serve as a point at which non-golfers can arrange to meet players after their round. One monument not to miss in Key West is the small round landmark which denotes the most southerly part of the continental United States.

    Restaurants and bars in Key West

    Duval Street is the popular centre of Key West in so many ways, not least when it comes to restaurants. When you are eating out from your Key West holiday rental of an evening, you may wish to sample popular outlets such as Nine One Five or Mangoes, or try the Banana Café for breakfast or lunch. Blue Heaven in the Bahama Village is the place to sample outdoor dining of the highest quality, with an indoor option available if preferred. The bars and clubs of Key West are plentiful in the extreme, with options to suit all tastes and requirements and allow you to party the night away in style.