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Holiday Homes in Summerland Key

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    Travellers to Summerland Key are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 22 Rentals in Summerland Key
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    Paradise n Summerland Key Cove1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Island Living1 / 15
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect getaway! Enjoy big boat access on a 62 ft wide, flow through canal, complete with 80 ft of concrete seawall dock and an outdoor shower. Only a 3-5 minute ride to open ocean. New washer/dryer Pet Friendly Situated on a lot & a third, this 4bd/2ba home offers room to lay and play in...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Oceanfront House1 / 50
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    What a find in renting this home. It’s one of the nicest we have stayed in since coming to the Keys. From the owner’s, to the manager, to the pool guy, to the grounds’ keeper...
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    About this property
    This luxurious, but cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area. (There is an island, located a few miles out directly in front of the home, was formerly...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation home sits behind some mangroves and has a view over Cudjoe Bay to the Atlantic. 4 bedroom and 2 bathrooms. Large deck with water access for a small boat. Water access has a shallow area to and from the deep area the boat would be docked at. Vacation home sits far off of the main road for a...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ”Gone Fishing” is exactly where you will be during your vacation time at this pristine home on Summerland Key, just 23 miles to Key west and 25 miles to Marathon. Relax and enjoy cocktails and snacks by the heated and chilled swimming pool after a great day exploring all the treasures the Florida...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Casa Manana,' the name affectionately assigned this beautiful gated property in Summerland (Ramrod) Key, is a uniquely situated private waterfront venue. Enter through the gates and you will immediately be transported into the tranquil, easygoing and thoroughly relaxing Keys lifestyle. Located on...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42' Sony flat-screen, hi-def TV with surround sound makes you feel like you are right in the middle of the action. Kitchen is a chef's delight with...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys. This stylish home is outfitted in Florida tropical style with cool and comfortable leather in the...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef's dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops. The...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home has three stories including a super play room off the pool area with a ping-pong table and a big screen TV for the kids. The 2nd floor accommodates a large...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining areas for friends and family....
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    This lovely 2 bedroom, 2 bath residence is located on Summerland Key at mile marker 24 just north of Key West for sightseeing, great restaurants or just take in the color of the local history in our southernmost most city. The home is comfortably furnished in tropical colors. Open kitchen, dining...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing. The shady screened porch overlooks the...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The open porch catches the breeze and sun with this Florida Keys vacation rental! Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all the comforts of home. This tropical setting will set your mind at ease in a true, Florida Keys style. The...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key where astounding sunsets and ocean vistas will be yours. The grounds are very shady and groomed with a nice Tiki hut at the waters edge. Plenty of dockage on the canal side and...
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    Location Information
    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Stunning Atlantic Ocean views from dining area, living room and both bedrooms. Sunrise on the left, sunset on the right and in between 180 degrees of open ocean. Our vacation home is located in exclusive Summerland Key (mile marker 24.5). Whether you are daring adventurer or a more indoor type of...
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    Location Information
    33042, Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PARADISE LIVING: Enjoy the view from our large porch overlooking a deep, wide, crystal blue clear canal with quick boating access to the Atlantic Ocean. Looe Key Coral Reef is a short distance away by boat for some of the best diving and fishing the keys has to offer. If you prefer to stay home,...
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    Location Information
    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Tropical home is a gem! Right on the water where you can enjoy beautiful afternoons and mornings. The home boasts a unique structure with spacious features, perfect for entertaining families and friends. Enjoy newly renovated kitchens, bathrooms and living spaces. This is not your average home...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Hot Tub
    • Internet Access
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    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in this two-bedroom, two-bath canal front villa for six when you come to Summerland Key and revel in rest and relaxation with your very own private pool and hot tub. And to make your vacation complete, you can bring three dogs along for a small nightly fee! This vacation rental is located on...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Patio
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom / 2 Bath Upstairs 1 King Bed, 2 Queen Spacious office with open water views 2 Bedroom/ 1 Bath Down 1 King, 2 twin 2 Separate living room areas, up and down, each with large flat screen TV's and DVD players Large screened porch up and down Heated Pool w/ outdoor shower and pergola...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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