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Florida Keys Vacation Rentals

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    Travelers to Florida Keys are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    Mina Bay - Oceanfront "Million Dollar View"1 / 19
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    About this property
    This Amazing Beach Home Has All That You Need!!! This House Has 3 Floors With Balconies With An Amazing View Of The Bay. It Has An Outdoor/Covered Space That Can Be Used To Hang Out And Cook. It Has An Outside Island Kitchen That Is Fully Stocked With Cooking Gadgets. The Private Beach And Boat...
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    Key Largo, Florida Keys 33037
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    This second level two master bedroom and two bath house is located in quiet Key Colony Beach neighborhood. It has an open floor plan with a large kitchen, dining and living room perfect for entertaining overlooking the canal through six double-sliding doors to enjoy the scenery outside while...
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    Key Colony Beach, Florida Keys 33051
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
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    Pet friendly
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    About this property
    Beautiful elevated home with views of the bay. Master suite is on the second living level with it's own porch. Fully equipped with everything you need for a relaxed vacation. Just bring your toothbrush. Key West is a short drive as well as the beaches at Bahia Honda state park. There is a dive shop...
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    Ramrod Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Beautifully decorated 2 bedroom and 1.5 bath townhome located at Buttonwood Bay.  This unit will make you feel right at home as soon as you walk through the front door.  The kitchen has been updated and has everything you need for your vacation.  The living room has a big screen tv.  Off the living...
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    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 1,500 sq. ft. townhouse with 2 large bedrooms with king beds, 3 full bathrooms plus covered deeded parking for your car. Fully equipped kitchen. Sleeps up to 6 comfortably as the downstairs living room has a queen sleeper and full bath. Luxury furnishings and appliances throughout make this...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Deluxe One Bedroom Condo1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
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    Pet friendly
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    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This second level two master bedroom and two bath house is located in quiet Key Colony Beach neighborhood. It has an open floor plan with a large kitchen, dining and living room perfect for entertaining overlooking the canal through six double-sliding doors to enjoy the scenery outside while...
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    Key Colony Beach, Florida Keys 33051
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Henry's Piece Of Paradise On The Ocean In Key West1 / 5
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • Sauna
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Scroll down to "About the owner" and in that box click on the "See more" button -...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    About this property
    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    Key Largo, Florida Keys 33037
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To tee, or not to tee: that is the question ... But whether or not golf is your game, the Key West Golf and Country Club promises a stay in one of the most esthetical residential neighborhoods in the Florida Keys. Beyond the masterfully designed 18 hole golf course, here you’ll enjoy the 200 acres...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
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    • Satellite TV
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated, a beautiful spacious 2 bedroom 2.5 bathroom MoonBay townhouse. Steps from the pool and bay dock. Tennis and basketball courts, kayak and fishing to enjoy your day in a resort style community of Key Largo Moon Bay. Enjoy a relaxing warm winter in the Keys. Available during...
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    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
    • Washer
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Water front Boat slip for 20-22 foot Jacuzzi Tiki hut Pool table inside Close to pennecamp park , winndixie , restaurants , all water sport activities and rentals . Good weather year round . Enjoy beaches , fishing access to ocean and bayside . Restaurants accessible via bay and Oceanside ....
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    Tavernier, Key Largo 33037
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Pelican Landing St. Thomas Penthouse1 / 24
    (29)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    • Grill
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    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
    Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. You are within the heart of the historic district and can walk almost everywhere. Although close to Duval, the home is a quiet escape from the hustle bustle. This small town house...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the minute you step foot in this luxurious condo, the water dominates your view and your activities. Oceanfront views from living room and master bedroom, 3 balconies... lush gardens, pool, palm trees, the finest sandy beach in the keys and the magnificent Atlantic Ocean are your constant...
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    Long Key, Florida Keys 33001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    Please note that this property has a 10AM check-out time. Straight shot to the Atlantic Ocean! Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Coral Condo1 / 22
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Southern Diversion Marathon see our spring special1 / 24
    (2)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Southern Diversion Two is an exclusive private gated estate located in Marathon in the Florida Keys. This sprawling 2 acre private estate is located directly on the gulf of Mexico featuring 300 feet of open water to capture the most breathtaking sunset views. There is deep water dockage and a...
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    Marathon, Florida Keys 33050
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 20
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Marathon, Florida Keys 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Absolutely charming, warm and inviting home. Single family home on lovely 12th Street in Key Colony Beach. Quick access to the ocean or gulf, with 80' of deep water dockage (with step down dock). Bait freezer, fish cleaning table, gas grill, hi speed wireless, 3 TV’s and 1 DVD Player. This large...
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    Key Colony Beach, Florida Keys 33051
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Marathon, Florida Keys 33050
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Tavernier, Key Largo 33070
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of it all, Plantation Key is the most convenient of all the Keys. We are near a supermarkets, a pharmacy, and a hospital. There are also plenty of restaurants and a movie theater. The neighborhood offers a boat ramp directly on the bay. Ocean access is a short ride through Snake or...
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    Tavernier, Key Largo 33070
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Shipyard 106-2 1 Bedroom newly renovated Condo1 / 17
    (45)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony on the 2nd floor deck. In case you would like to work on vacation the unit has a wireless DSL connection. There is one assigned parking space per unit....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise. Our home features 3 bedrooms and 2 bathrooms. 2/1 upstairs and a 1/1 separate suite downstairs including a mini kitchen. Beautiful views from the patio also provides privacy with no "backyard neighbors". Your rental also includes 2 bikes and a kayak to enjoy. We are on the same...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful Canal Home - Minutes From Open  Water1 / 38
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweet Magnolia is an awesome home on an oversized corner canal with 175' of canal frontage. This property offers lush tropical landscaping, a huge 2nd story lanai overlooking the canals, and privacy galore. You will find everything you need and desire at this home! Each bedroom comes equipped with...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    • DVD Player
    • Parking
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Paradise Found  2 Bedroom Condo with a Shared Pool1 / 16
    (55)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Housekeeping Included
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Yard
    • Satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home on stilts. The home is equipped with all that is needed for a vacation. Private pool (heater is optional). Sleeps eight and its very close to shopping, beach, restaurants and more! Sombrero Beach is 5 minutes away and you can spend the entire day swimming, walking or just relaxing....
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    Location Information
    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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