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Vacation Rentals nearby Smathers Beach

South Roosevelt Boulevard, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Key West
    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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    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
    (28)Very good
    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (6)Excellent
    1.7 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    The pictures do not do it justice!!..The house had been completely renovated and updated..Beautiful flooring, appliances , electric blinds on every window and big screen...
    Reviewed May 24, 2018
    We booked with Jennifer and she was amazing. Very accommodating and easy to contact. When we got to the house it was even better than the pictures. It was very spacious and...
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    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included. Dogs are...
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    Key West, Florida Keys
    Holiday Rental House - 3 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 June 2, 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 October 24, 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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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (1)Excellent
    1.7 kilometres from Smathers Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed April 12, 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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    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 July 16, 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 July 7, 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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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (8)Excellent
    2.2 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 27, 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
    Reviewed January 26, 2018
    Recently spent 10 days at KWO. This property is superb and reflects a pride of ownership. KWO clearly exceeded the already impressive presentation on the website. Paula and...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Atlantis House Master Suite1 / 44
    (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 December 29, 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 December 17, 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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    Studio Blu1 / 15
    (1)Excellent
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2017
    We stayed at Blue on White Jan-Mar of 2017 and couldn't have been happier with our choice! The apartment is cozy (it is a studio) but at the same time is well maintained and...
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    About this property
    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this nightly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided! This property will meet all of the demands a...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.5 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bed 2 Bath Waterfront Key West Condo on Smathers Beach Peaceful views and tropical breezes of the natural salt ponds, acting as a bird sanctuary for native species, will help you relax in a fully furnished and updated 2 bedroom / 2 bathroom property sitting on Smathers Beach in Key West, Florida....
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    Key West, Florida Keys
    Condo/Apartment - 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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    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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    • 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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    0.7 kilometres from Smathers Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Balcony
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    • Washer
    • 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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    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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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 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
    • Internet Access
    • Grill
    • 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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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. Courtesy Shuttle available to condo from airport and ferry terminal. A private parking spot is...
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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
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • 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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    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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    Kali Zoi House - 28 Day Minimum1 / 27
    (1)Excellent
    2.2 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2017
    We had the best time staying at the Kali Zoi house! The location is absolutely perfect as everything seems to be walking distance. There were 5 of us in the house and there...
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    About this property
    28 DAY MINIMUM RENTAL TERM ONLY Kali Zoi is Greek for “good life.” That's what you'll have when you book a stay in this large, classic conch style house in historical Old Town. This 1,960 square foot, 2 story house has all of the charm of a 19th century home but was actually built in 1988 so it has...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Verandah1 / 24
    (11)Very good
    2.2 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2012
    We enjoyed everything about our wonderful home in Key West. We felt right at home, great location, we could walk everywhere, short drive to the beach, harbor, and restaurants...
    Reviewed September 2, 2011
    Everything was great about my stay. At Home Key West is great to work with and very easy to get in touch with should an issue arise. The location of this house is great, and...
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    About this property
    VERANDAH (monthly rental): - Tucked away on historic Frances Street lies your island escape… Verandah is a stunning monthly vacation rental -- two bedroom two bath home with a private pool and plenty of space for your family to stay and play! A gorgeous front porch surrounded by tropical foliage...
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    Location Information
    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
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    • 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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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
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    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful views, resort amenities, and a dog-friendly policy await when you book your stay at this charming condo on the eastern shore of Key West! Located within the upscale Sunrise Suites Resort community, this excellent rental is perfectly situated for you to explore Key West by day and relax...
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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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    • Internet Access
    • Cable/satellite TV
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    • Hot Tub
    • Balcony
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make those dreams of a beach getaway a reality and book your next Florida vacation at this luxurious Key West condo. With upscale resort amenities like a shared pool and hot tub, tennis courts, a fitness center, and a covered parking space, your vacation will be packed with tropical excitement from...
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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
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    • 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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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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
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    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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    0.2 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four-bedroom, three-and-a-half-bath Key West home has a private heated pool, a covered lanai, and an upper deck, as well as beautiful views from every window. It's situated in the exclusive Key Cove Landings, right on the water and within walking distance to grocery shopping, restaurants, and...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Cottage w/ shared pool, private hot tub, & street parking - Dogs OK!1 / 27
    (14)Very good
    2.1 kilometres from Smathers Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Terrace
    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2016
    This quaint villa was perfect for our party of 2 (might be a bit crowded for 4 adults, but for 2 kids it should be just fine!) The 1/1 was well appointed with everything we...
    Reviewed September 21, 2015
    We loved our stay here. It was decorated nicely, clean, and quiet. Housekeeping came in daily and did a good job. I liked the setup of the condo a lot; a nice, spacious...
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    About this property
    Treat yourself to a much-needed getaway filled with stress-free days and sun-soaked afternoons when you book your escape to this Key West retreat. Offering the chance to enjoy a private hot tub, street parking, a shared pool, and easy beach access, this home will make sure your stay is one to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2.2 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GREEN ORCHID (monthly rental): Have you been dreaming of living like a local in Key West? Your dream can come true. Green Orchid offers a true Conch Cottage experience on a narrow lane in one of the last historic Old Town neighborhoods. Situated on a lane that is only one block long, get to know...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 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 March 15, 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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    1.3 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • DVD Player
    • Sauna
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.8 kilometres from Smathers Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    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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    2.2 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, 7 nights blocks, Friday or Saturday changeover only. DELUXE 2 BEDROOM CONDO: This is a 2 bedroom, 2 bathroom condo unit that features a full kitchen and a flat panel television. All newly refurbished and decorated in an island inspired elegance. The unit also has a private...
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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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    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Grill
    • Internet Access
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed for a small nightly fee....
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 November 11, 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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    0.2 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Balcony
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning property overlooking the Gulf of Mexico boasts panoramic views from nearly every room and the private pool. Designed with hand scraped bamboo floors and a beautiful wraparound deck with several different seating options, this waterfront home is perfect for families or group getaways....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 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
    • Grill
    • Air Conditioning
    • 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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    0.2 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury awaits in this cozy yet spacious four-bedroom, four-bath Key West home, featuring a private pool and Jacuzzi, as well as close proximity to all the major locations. It's ideal for multiple families and large groups offering accommodations for up to 10. You'll enjoy the out-of-the-way...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.2 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    • Washer
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this elegant, waterfront rental in Key West serve as home base for your next Florida vacation, and enjoy a private pool and covered deck with ocean views, among other fine amenities. The rental is located in the private community of Key Cove Landings within walking distance to the essentials...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.2 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Internet Access
    • Patio
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool, a Jacuzzi tub, and a balcony with sweeping ocean views. You'll be centrally located in the heart of Key West in the exclusive Key Cove community. Walk to grocery stores and a...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.2 kilometres from Smathers Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Internet Access
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely four-bedroom, four-bath home for 10 provides a prime location and excellent amenities, including a private pool, a Jacuzzi, and a covered balcony with sweeping ocean views. You'll be located on the north side of Key West in the exclusive Key Cove community. Walk to a shopping center,...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2.1 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Patio
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the ideal spot for your next large group getaway, then look no further than this grouping of three separate Key West condos. Boasting a shared heated pool and hot tub, and space for up to 12 guests, this home makes it easy for everyone to enjoy all of the local attractions....
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Terrace
    • Washer
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway! What’s nearby: Located right near the water, you’ll be in a prime spot to sample all of the island's many charms....
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Internet Access
    • Terrace
    • Balcony
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West. This home...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2.0 kilometres from Smathers Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    • Grill
    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sip a mug of coffee on the balcony as you take in views of the Florida sunrise at this superb Key West condo. Complete with luxurious amenities like a community pool and hot tub, a private parking space, and a dog-friendly policy, this wonderful vacation rental is sure to delight. The 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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    2.1 kilometres from Smathers Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Grill
    • Patio
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West home is waiting for you and your group of up to nine to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner at Salute, then...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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