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Florida Keys Island Rentals

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    Travellers to Florida Keys are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    1 Bedroom, Sleeps 3Quick View
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    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your private deck only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these environmentally...
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    Marathon, Florida Keys 33001
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, Sleeps 8Quick View
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    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76. Near the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    Decorated in shade of sea foam and coral, this property is located in the Truman Annex and puts all of Key West's top attraction within easy walking distance. French doors open to a garden with hibiscus and cat palms framing a comfortable patio. Both bedrooms have queen beds, with a sofa bed in...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 3Quick View
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    Trailer 1 Bedrooms, 1 Baths, Sleeps 3 possibly 4 if small children. Newly renovated property. 33 foot RV with attached 30 foot A/C enclosure and Tikki. Only Full month rentals between Jan 1 to March 31. New Kitchen with Stainless steel appliances, 3 burner BBQ, 3 TV, free cable, WIFI available...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, Sleeps 6Quick View
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    This condo is located on Mile 104 on one of the best areas of the Keys and just few miles of Pennekan Park and Harris Park. The Apartment has been redecorated and on floor 4 with spectacular views of the bay and stunning sunset.
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully equipped eat in Kitchen, Washer/Dryer. Expansive private balcony overlooking the lush...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Half duplex located in prestigious Key Colony Beach. Tropical decor throughout. Located on a 100ft. wide canal with quick access to ocean. There is a concrete dock for your boat, and a great patio in the back. You are within walking distance to the "Cabana Club" , a private beach club with a...
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    Key Colony Beach, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    Neat, clean and perfect for a family vacation. This 2 bedroom, 2 bathroom home sits on a wide, deepwater canal Comfortable beds and furniture. Plenty of parking and room for a boat trailer onsite Optional access to a pool at the Glunz Ocean beach club $12 per person per day Outside Covered...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    Comfortable open floor plan coming in from large screen porch and wrap around deck overlooking extra long new dock directly on Bogie Channel. All 4 bedrooms are spacious with two Kings, Queen and twins in the bedrooms all located off a central hall. Large covered area under house and deck for...
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    Big Pine Key, Florida Keys 31581
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 12Quick View
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    • Private Garden
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    About this property
    Beautiful Beachfront home located directly across the street from famous Sombrero Beach. Sombrero Beach is surely one of the stand-out beaches in the Florida Keys. This pet friendly beach has something for everyone. Kayaks, boating, fishing & biking all easily available for great fun in the sun....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Key Colony Beach Canal Front Property. Nnew deep water boat dock (37.5 ft) directly at your back door with a fish cleaning table, water and power on dock. bait freezer 5 min. boat ride through the 100' wide canal leads toVaca Cut and the Atlantic Ocean and quick access to the Gulf of Mexico...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Ocean view, private beach and marina, free parking, tennis courts, swimming pool Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Futura Yacht Club is located in the Upper Florida Keys, on mile marker 88, directly on the Florida Bay. If you are accustomed to quality, and want to stay in a beautiful property that is centrally located, this is the place for you. Surrounded by local places to enjoy a delicious, fresh-caught meal...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 2Quick View
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    About this property
    Updated and comfortable 2 bedroom, 1 and 1/2 bath condominium in Moon Bay Resort in beautiful Key Largo, Florida. Pool, tennis court, marina with boat slips and clubhouse are just some off the amenities. This property has a screened patio and covered parking space . Condo is fully equipped with...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    ocean front paradise with 95 feet of ocean frontage. Exotic natural serene setting with easy ocean swimming and access. Customer responses equate it with a resort atmosphere and very unique dense fauna sheltering trees, flowers,and visits frequently by humming birds, tree frogs and the like....
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size Sleep Number Bed - Fully...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 2Quick View
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    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast.LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET...
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    Islamorada, Florida Keys 33036
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    Amazing ocean views can be enjoyed from this beautiful stilt home with separate mother- in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 4Quick View
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    Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy ride under some bridges to Pine Channel with decent...
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    Lower Keys, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your living room sofa, only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these...
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    Marathon, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Paradise point! This is a newly renovated (Spring 2014) home in a private gated community. Located at mile marker 106 on the bayside in Key Largo, this home is an ideal location for those looking to enjoy life on the water in the Florida keys. The home is situated for convenient access to...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    Enjoy this lovely two bedroom two bath garden and pool view unit at 1800 Atlantic, You even get a peep of the ocean from your 40ft private balcony. Located at the Premier 1800 Atlantic complex on the Atlantic ocean at the end of Smathers Beach. This unit has all you need to enjoy and relax with all...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, Sleeps 2Quick View
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    About this property
    Unit 8c is an efficiency in a tri-plex located about 50 yards from the Ocean. It has a queen size bed, futon sofa and a small dining table with 2 chairs. The efficiency has a medium size kitchen with sink and medium size refrigerator, four burner stove. It also has a private bath with toilet, sink...
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    Marathon, Florida Keys 33050
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 11Quick View
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    About this property
    Tiki Beach is a 3 bedroom, 2 bath bungalow located on the Gulf side of the island of Big Pine Key. Over an acre and a half with 150 ft of open water frontage and a private pool, hot tub and lighted dock that allows for a boat with up to a 3 foot draft at average tide levels. Water supply on dock...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
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    2 Bedrooms, Sleeps 6Quick View
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    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    About this property
    Waterfront Condo rental includes HD Comcast Cable on 2 New Samsung LED 3D HDTVs (55' & 32'), WiFi, Electric, Water, Parking, 36' Boat Slip on the seawall behind the condo available upon advance supply of registration/insurance doc approval, and an Airport on the club grounds. Personal Golf Cart for...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    About this property
    Cabana in beautiful Sunshine Key Resort, Golf Cart,great fishing, breezes, and relaxation. 1 bedrooms, 1 bath, kitchen and living room. Outdoor tiki. enjoy the island living of the Florida Keys. Great resort amenities.Marina available in resort, park your boat, jet sky, and enjoy your vacation...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. Very Clean 2 bedrooms, 2 bath home with over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap around walkway....
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy cottage , one bed room studio style with private bathroom and kitchenette.Great location close to local restaurants and bars,2 miles to John Penny Camp State National Park and walking distance to Swim with the Dolphins. .shopping plaza. Bisycles for rent. $10
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. Our home is third from the waters edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean Front - Villa Bali inspired Florida Keys beauty on Privately owned Walker's Island. This is a spacious 5 bedroom, 5.5 bath home with luxury in every detail and design. Features include cathedral ceilings, marble, stainless steel and and mahogany finishes, and fireplaces in the living room...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Spacious apartment in Quite street, Key Largo Recently remodeled one bedroom apartment centrally located in the Heart of Key Largo. Private, Safe and Quiet residential neighborhood within walking distance to John Pennekamp National Park. Kayak right into the parks beautiful mangrove canals and...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful 3-bedroom home on mile marker 90 in the Florida Keys. Our home is located in Tavernier, the Sport Fishing Capital of the World. It is a private, gated home directly on the water with a small pier and...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    Fantastic 1800 Atlantic Penthouse in the highly desirable East building of the facility 2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared, previously owned by the VP of Sony his taste was impeccable. The Master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bayside condo in a 10 unit complex overlooking dock and canal. This unit is located in the center of Key Largo with access to shopping and great restaurants. Perfect for the avid diver or fisherman as there is a dive shop and bait shop located in the complex. This is a 1 bedroom with a King bed...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    This Secluded and Private HOME has a spectacular Ocean View, located two miles from the main Highway US1 in the North Key Largo. This house fronts on the John Pennekamp Park Waters with a breathtaking ocean view. Relax in the 500 square foot second floor balcony and enjoy breakfast while watching...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently been renovated and features a new kitchen with granite counters, lovely open floor plan with vaulted ceilings. The elegant master bathroom has a spacious walk in shower. The master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean. This unit has a remodeled Kitchen and bathrooms also. Guest pays $200 cleaning fee in addition to the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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