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Holiday Rentals near Smathers Beach

South Roosevelt Boulevard, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Key West
    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 50
    (69)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 12
    (31)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Key West Condo close to the Ocean1 / 47
    (4)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tropical Escape1 / 52
    (85)Very good
    1.5 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    This place is just perfect! Nice and clean, and check in was a breeze! But what I really loved about it is the location! You are in Key West, but you are far enough away from...
    Reviewed 7 July 2017
    Owners were great and very accommodating. The condo is beautiful. Has everything you need. Pool was great to use. We would rent again when we come to key West. We had a great...
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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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Atlantis House Master Suite1 / 22
    (23)Excellent
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
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    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    We stayed two nights in the Master suite. (Our second time at the Atlantis House)It was another beautiful experience- everything was prepared with special care from the Turkish...
    Reviewed 17 December 2015
    My husband and I stayed with Kayla and Steve for five days and it was the most relaxing fun filled stay ever. The accommodations were very clean and our hosts were the...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 39
    (39)Excellent
    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Kathy and Bob have a great large two bedroom condo with generous resources; tv in each room, radios, games, wet bar, great space for cooking and lots of beach supplies: bikes...
    Reviewed 17 June 2017
    Everything with this rental was first rate from start to finish. Kathy, the owner, checked in with us multiple times in the weeks leading up to our arrival to make sure we knew...
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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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 19
    (16)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 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 14 July 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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A convenient hideaway for your Key West and Lower Keys adventures, this two-bedroom condo is tucked into a quiet complex near shopping, bars, live music, beaches, and Mallory Square. Cozy, fully-appointed rooms include everything you'll need for your Key West vacation but your own clothes. With...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Key West Florida Beachfront Condo1 / 22
    (4)Excellent
    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    Mrs Carol thank you for the beautiful place to stay in for a beautiful trip. The views were awesome from the room. The sunsets you can watch from balcony was dream like. Highly...
    Reviewed 24 October 2017
    I went to Key West with four other childhood friends for a 50th celebration! We booked our week five months prior, and of course hurricane Irma ravaged the Island. We...
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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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunrise at Seaside Condo 2 Bedroom1 / 17
    (24)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2018
    Condo was wonderful. Pool beautiful. We were far enough from Duval St. to have plenty of peace and quiet and near enough to be there whenever we wanted. Condo had everything we...
    Reviewed 18 November 2017
    I would stay there again. Pool was also nice. Bonnie was always assessable And Easy to talk to. Plenty of room inside. Washer and dryer and full kitchen
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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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Family friendly condo w/ shared pool, hot tub, & complimentary shuttle! Dogs ok!1 / 27
    (1)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Balcony
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool and a complimentary shuttle. With the resort's complimentary shuttle, it's easy to get to the airport and the ferry terminal. Enjoy bird watching...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    >1 / 40
    (1)Very good
    1.6 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Sauna
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2017
    Beachfront condo, great pool, hot tub and grounds area. Poolside bathrooms have saunas, large rec room, library & a small gym that was a nice addition.Very secure with gated...
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    About this property
    The Grand Vista - 2 bedroom suite 2 Bedroom 2 bath suite, Totally renovated with flat screen plasma TV's in both bedrooms and the living room. All brand new furniture in Jan 2010, King bed in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in the living room. Full size...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.9 kilometres from Smathers Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this your Key West Vacation home! Cozy 2 bedroom, 1 bath home set on the back half of a residential lot with new kitchen, bath, and furniture. Privacy provided by the fenced outdoor area, with a shaded porch and furnished gazebo for relaxing. The location is 5 minutes max to anywhere on the...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 bedroom Condo Presented Key West Style1 / 28
    (145)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    Mrs. Pam was very attentive to our needs, just felt very confortable at the place and with the reservation. Thanks
    Reviewed 9 August 2018
    We have enjoyed our stay at the condo. It has everything that we needed during our stay, it’s very clean and feel like home. It’s prettier than the pictures show. We definitely...
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    About this property
    This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    1.7 kilometres from Smathers Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    Loved Jen and Mitch! Very welcoming! Made everything very comfortable and relaxing! Thier friends and neighbors are very nice and welcoming too! We enjoyed a cookout, a...
    Reviewed 13 April 2018
    My husband and I enjoyed a 3 day stay on the Fat and Sassy. The owners are welcoming and helpful with any questions or recommendations you it need. The marina is perfect, with a...
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    About this property
    Join us in Key West where we are docked at a beautiful Marina. Enjoy all the comforts of home and the added beauty of the Ocean. There are pools and a Waterfront Bar & Grill for your enjoyment. We will be Aboard in the private owner’s suite to make sure your stay is hassle free and exciting....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    KEY WEST LA BRISA CONDO - North Building1 / 24
    (1)Excellent
    1.5 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Our party of 6 (2 adults, 2 boys ages 23 & 19, & 2 16 year old girls) rented this in July. Room was very well appointed. Everything we needed was provided. Well stocked...
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    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. Our condos' at La Brisa are two bedrooms with two full bathrooms on the third floor. The master bedroom has a king size bed with a walk...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    2.1 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool. Awaken your senses with tropical breezes, turquoise waters and Key West Sunshine in this brand new 2-bedroom, den, 3-bath home. A secluded location yet the best of both worlds allows...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.8 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Washer
    • Wi-Fi
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    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1.8 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home that accommodates 8 guests to enjoy the large outdoor dining area while viewing your private pool in your fenced yard. This classic 3-bedroom Conch home is located across the street from Bayview Park, with tennis courts, playground, basketball court and community activities. Built in...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Flagler Station1 / 25
    (1)Excellent
    1.8 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying. This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.8 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West home with boating and private swimming pool! Lovely, well appointed home, remodeled, granite and stainless appliances, 2 bedrooms, each with ensuite baths, 3 baths, tile and wood floors throughout. Open living and kitchen, living room and master bedroom opens to swimming pool and boating...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    0.7 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and the fresh ocean air of...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Henry's Piece Of Paradise On The Ocean In Key West1 / 26
    (36)Excellent
    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Hot Tub
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2018
    We stayed 5 nights. It was even better than I anticipated. The condo was secure with private parking. The kitchen had everything we needed. Loved the Key West color scheme in...
    Reviewed 4 March 2018
    Henry's Piece of Paradise is just that. Beautiful condo w lovely furnishings, created w whimsy & color. Comfortable and well equipped kitchen & large balcony. The pool...
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    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condo On The Ocean with partial ocean views - rent weekly or nightly. Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Seaside Condo 2 pools summer specials1 / 17
    (2)Excellent
    1.6 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    This apartment was the perfect place to experience Key West, it was sunny and quiet, right across the street from the beach and just minutes away to Old Town with it's great...
    Reviewed 12 March 2016
    This Key West getaway condo is a wonderful escape from the freezing temperatures of the northeast. I was here other years and noticed this time that there is a beautiful new...
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    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation. This...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Terrace
    • Parking
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is sure to become your new favorite...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • DVD Player
    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this inviting Key West condo your home base when you come to Florida, and prepare yourself for a sunny, fun-filled, and convenient getaway with family or friends. Located right near the water's edge, this home makes it easy for you to partake of the sunny, sandy beach whenever you like....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Parking
    • Terrace
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and unwind with this comfortable and inviting two-bedroom condo! A shared pool and a private balcony with scenic views of the marsh add to the feeling of relaxation. The family dog is also welcome to join you for an additional nightly fee. This colorful rental is part of the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    • Central Heating
    Suitability
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
    • Hot Tub
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.1 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool. Poolside Paradise was built with entertaining in mind. Privacy fence surrounds the intimate front yard perfect for gathering, wet bar is welcome addition in the kitchen,...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brisa Del Mar1 / 24
    (13)Very good
    1.6 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Balcony
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    This condo was just what we wanted. It had everything we needed including beautiful views. The condo was clean and the beds comfortable. The pool was great and the hot tub was...
    Reviewed 8 January 2014
    The condo at Barisa was perfect, lots of space and breath taking views every day. Everything you could possibly need was right there. Not far from old town and all the beaches...
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    About this property
    Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental! This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean. Enjoy spectacular views from this waterfront rental condo in Key West of the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Meadows House1 / 19
    (23)Very good
    1.9 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    3 of us booked for a bachelorette party in Key west, and couldn't be happier with the accommodations! The house was in a well kept neighborhood, inside the decorations were...
    Reviewed 15 November 2017
    We had a lovely stay in this condo at Key West. Spacious and well furnitured. Location is nice, nearby everything in Key West. We rented bikes which were delivered at the house...
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    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Exclusive Key West Beach Front ~ Weekly Rental1 / 21
    (4)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    My reviews are always as fair and honest as I can be.. VHKW were very professional... they provided all the info we needed very promptly and returned questions ASAP. The room...
    Reviewed 22 August 2016
    Home was nice, could not beat the views day and night. All the amenities you need are there for you, if needed.
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    About this property
    Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.3 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1.7 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Private Garden
    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Strikingly set in the oft-missed Key West mid-town neighborhood, we find Island Elegance, making a classical curbside statement with its craftsman-colonial architecture, lush mature tropical landscaping, and white picket fencing. Built in 2005, the design of this home incorporates the timeless...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.9 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in one of the most sought out neighborhoods 'The Meadows' this lovely condo has everything you need to enjoy your time in Key West. Nestled in the ever popular local residential neighborhood known as The Meadows, this sweet spot is a 2-bedroom 2-bath upper level condo in a home with a...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.7 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Terrace
    • Central Heating
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space. A quintessential cigar makers shotgun style house built circa in 1890s. Located in one of the most desirable historic neighborhoods of Key West – The Meadows with tree-lined...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Internet Access
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Give your family and friends the trip to the Florida Keys they deserve thanks to this condo in Key West! A great location, along with amenities like a shared pool and private parking, ensure everyone can enjoy themselves. A dog is even welcome for a small nightly fee. Courtesy Shuttle available to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
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    • Patio
    • Hot Tub
    • Grill
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed 31 July 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with island vibes and a...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the laid-back ambience of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have you relaxed in no time. This...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this cozy and chic Key West luxury house your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. You'll be situated only six blocks from the beach for fun in the sun anytime you want it, and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.8 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    A Tropical Tradition (Gallup Arms) ~ Weekly Rental1 / 10
    (2)Very good
    1.9 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2017
    This is a very cute home. It certainly fit our needs in the home itself. Quite a walk to Duvall St. but if you don't mind walking it is okay. If you are not renting the...
    Reviewed 3 May 2016
    We loved this property - plenty of space for myself, my husband, his mother and our two big teenage boys on the three floors. It was well equipped and a high standard of...
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    About this property
    Nestled in one of Key West's original gated 'mini-compounds,' the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Great for families! Free shuttle service, private patio, shared pool & hot tub!1 / 24
    (1)Average
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Terrace
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay cool on your next trip to Key West with a stay at this delightful condo with a private balcony, a shared pool, and a complimentary shuttle between the rental and many of Key West's popular attractions. Located just minutes away from beaches, marinas, scuba shops, and the Key West...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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