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Holiday Rentals nearby Smathers Beach

South Roosevelt Boulevard, Key West, Florida 33040
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    ₹ 12,346 Average
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    Travellers to Key West are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 100 Rentals in Key West
    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 25
    (67)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 12
    (29)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Sunrise at Seaside Condo 2 Bedroom1 / 26
    (24)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • 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 19 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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    Key West Condo close to the Ocean1 / 26
    (4)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2018
    This is the second time we have stayed at this property, the first being in 2016. It still is a conveniently located, quiet and peaceful condo with reserved parking. It is...
    Reviewed 25 January 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Escape1 / 26
    (85)Very good
    1.5 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • 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 8 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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    Elegant, Two Bedroom Condo Close to the Ocean1 / 17
    (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 15 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
    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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    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 2 weeks ago
    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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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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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 25 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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    Flagler Station1 / 25
    (1)Excellent
    1.8 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FLAGLER STATION (monthly rental): This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and re-furnished. Large spacious living room and dining area allow plenty of space for entertaining with easy access...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Terrace
    • Grill
    • Air Conditioning
    • Parking
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CAYO HUESO SUNSHINE: 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 you an easy stroll over to the sandy shores of Smather's Beach or just a few blocks from the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Parking
    • 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 18 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 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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    • Grill
    • Air Conditioning
    • Balcony
    • Parking
    • 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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    Stylish, dog-friendly condo with shared pool, hot tub, and complimentary shuttle1 / 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
    • Grill
    • Internet Access
    • Balcony
    • Cable/satellite TV
    • Parking
    • 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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    Location Information
    Sugarloaf Key, 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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    • Parking
    • Internet Access
    • Hot Tub
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    • Cable/satellite TV
    • Balcony
    • 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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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Balcony
    • Grill
    • 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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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 bedroom Condo Presented Key West Style1 / 28
    (143)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 5 weeks ago
    I am retired military and wanted to stay on one of the base facilities. Due to availability I was unable. I found this condo on Trip Advisor and contacted the owner. Miss Pam...
    Reviewed 10 July 2018
    My husband and I, along with our two adult children stayed here for a long Key West weekend. The location is convenient to shopping, grocery stores, scooter rentals, etc. Far...
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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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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Hot Tub
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    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    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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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    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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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Balcony
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your next Key West vacation at this lovely condo in the Florida Keys. This rental comes equipped with a shared pool, hot tub, and tennis courts, along with central air-conditioning, a private balcony, and a fitness room. The resort also offers a courtesy shuttle for easy access to and from...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.1 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd prefer some shopping and...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.9 kilometres from Smathers Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Location Information
    Key West, 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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    • Grill
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • 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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    Cute, dog-friendly condo w/ free shuttle, private patio, shared pool and hot tub1 / 24
    (1)Average
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Balcony
    • Cable/satellite TV
    • Hot Tub
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    • 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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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunny condo w/ amazing views features shared pool & hot tub - dogs welcome!1 / 27
    (1)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Grill
    • Balcony
    • Hot Tub
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2015
    We came in a small plane, so we needed to ship our luggage down to Key West. The office staff allowed us to ship it right to the check in office. The suite had two rooms and a...
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    About this property
    Escape to your new getaway of choice on the Florida Keys! This two-bedroom and two-bathroom condo by Key West has it all, from a fantastic location and dog-friendly accommodations to lovely resort amenities. Courtesy Shuttle available to condo from airport and ferry terminal. Back at home, you...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dog-friendly condo w/ shared pool & hot tub perfect for exploring Key West!1 / 26
    (1)Terrible
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This dog-friendly home in Key West offers swimming, sunshine, and access to sandy shores. A courtesy shuttle is available to the condo from the airport and ferry terminal. A free, off-street parking spot is available with your rental. Resort amenities like a shared pool and hot tub let you spend...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 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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    • Balcony
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    TRUE PARADISE: 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 total of 5 that share a serene pool and outdoor seating for lounging and grilling. The building itself dates back to 1938 and...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 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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    • Hot Tub
    • Balcony
    • Air Conditioning
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    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise awaits when you book your next Florida vacation at this lovely two-bedroom condo on the sunny shores of Key West. With lush tropical landscaping and exclusive resort amenities like a pool, hot tub, and tennis courts, you'll never want to leave! This rental is located in the upscale resort...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.6 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Washer
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready to see a whole new side of the sunshine state from the comfort of this home in Key West. You'll enjoy perks like a private pool, as well as a great location just a few blocks from the beach! Nestled on the eastern edge of Key West, this home is a short walk from the soft sands of Higgs...
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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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    • Grill
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    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    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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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy sunshine, sand, and surf in the gorgeous Florida Keys with this two-bedroom, two-bathroom home on Key West. Between the shared pool, soft beaches, and shopping and dining downtown, you'll be sure to have a great time. Courtesy Shuttle available to condo from airport and ferry terminal. A...
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    Location Information
    Sugarloaf Key, 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
    • Hot Tub
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip away to the laid-back atmosphere of the Florida Keys with a stay at this private Key West condo. This rental boasts amenities like a shared pool, a private balcony, a complimentary shuttle, and lush tropical landscaping to ensure your getaway is one to remember. This condo 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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    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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    • Grill
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
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    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue waters, warm winds, and the Florida sun await when you book a stay in this delightful two-bedroom condo with a private patio and heated community pool! Conveniently located just a few minutes from the Key West International Airport, this rental is part of the beautifully landscaped Sunset...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 kilometres from Smathers Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private heatedpool, luxurious patio area, covered...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    West-facing, bright and sunny condo w/ shared pool & hot tub, tennis, & parking1 / 27
    (1)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2014
    We had a great night at sunrise suites. It is not central, so you have to get a taxy to go downtown. Because you have a sunset drink, wine with dinner and one before going...
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    About this property
    Watch the sunset from the comfort of your private balcony at this lovely Key West condo. You'll also be treated to superb resort amenities like a shared pool and hot tub, tennis courts, and lush tropical landscaping, making this rental a sure bet for a luxurious Caribbean getaway. This condo is...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lovely condo w/ shared pool & hot tub right nearby the beach - dogs OK!1 / 27
    (2)Average
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2015
    We found the unit was as advertised, and clean, quiet, and comfortable. Most things worked well, though one of the locks on the door didn't work, and the lock on the patio door...
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    About this property
    Get your next great vacation started with this dog-friendly Florida home! All of Key West's most amazing sights are yours to experience, with plenty of amenities awaiting you at home. Courtesy Shuttle available to condo from airport and ferry terminal. Soak in the shared hot tub, or swim in the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.9 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
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    • Air Conditioning
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of eateries, a market, and...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Dog-friendly condo with tennis, shared pool, hot tub, and private balcony1 / 24
    (2)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2016
    The location is nice because it's quiet. The unit and kitchen supplies need updating. The view from the balcony is nice. The pool area is nice.
    Reviewed 15 March 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it...
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    About this property
    Leave your troubles behind and head for the beach with this delightful and dog-friendly Key West condo! Incredible amenities like a shared pool and hot tub, tennis courts, and a private balcony with views of the marsh ensure you'll have a vacation to remember. Located in the upscale Sunrise Suites...
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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 condo w/ scenic views, shared pool & hot tub, balcony & parking1 / 25
    (2)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Hot Tub
    • Parking
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2016
    My boyfriend and I checked in with another couple for a little under a week. The room was clean and was located within 5 miles of Duval Street. We all had a great time!
    Reviewed 31 May 2016
    We booked this with friends through trip advisor and really enjoyed our 1 night stay, rooms were spacious and comfortable with all mod cons and there was a great pool area.
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    About this property
    Pamper yourself with a stay in this luxurious and sunny Key West condo. Surrounded by beautiful tropical landscaping, and boasting resort amenities like a pool, hot tub, tennis courts and a private balcony with views of the Salt Ponds Preserve, this comfortable rental will have you relaxed and...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CASA DE ROSALIE (monthly rental): 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 1889 with original Dade County Pine in the bedrooms and a gracious banister for the stairs to the...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip away to the Florida Keys with a stay at this two-bedroom, two-bathroom condo with a private patio, beautiful tropical landscaping, and a shared pool for cooling off! This condo is part of the high-end Sunrise Suites Resort in Key West. With a fabulous location just three miles from the city...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Breezy dog-friendly condo w/ private deck, shared pool/hot tub, & parking space1 / 33
    (1)Excellent
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Hot Tub
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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    About this property
    Grab your sunglasses, pull up a lounge chair, and relax beside the lagoon-shaped community pool at this upscale Key West condo! From gorgeous tropical landscaping to a private balcony and a dog-friendly policy, this comfortable rental has everything you need for the ultimate Key West experience....
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Dog-friendly condo w/ water views, shared pool & hot tub, and free shuttle1 / 27
    (1)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2016
    Beautiful room. Balcony has a lovely view and also overlooks the airport runway, which was actually kind of cool being a small airport. Comfortable bed, clean, and homey. TV in...
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    About this property
    Book a stay at this lovely condo for a relaxing tropical getaway in the heart of the Florida Keys! With incredible amenities like a shared pool and hot tub, lush landscaping, a private parking space, and beautiful views of the Salt Ponds Nature Preserve from your balcony this rental is truly 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
    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 cottage 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. And the real bonus: you can bring your favorite canine friend along, too. You'll be situated only...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 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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    • 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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