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Florida Keys House 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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    3 BedroomsSleeps 8Quick View
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Review
    2 BedroomsSleeps 8Quick View
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    Located in the heart of the national key deer preserve this bright chalet style home with many windows, with very comfortable memory foam mattresses in all the beds, master room has a queen size bed with a 40' flat screen TV, and the guest room is equipped with a very sturdy wood bunk bed with a...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    About this property
    Hello prospective guests! Our great little spot is only a monthly rental but I am sure you will find our rate for a month is less expensive than most for a week. Please consider a longer stay on our island while saving some money by doing so. In a great location,nestled underneath a Spanish...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    23 Reviews
    1 BedroomSleeps 4Quick View
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    With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Abaco Suite, is a bi-level suite with a very spacious...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Review
    2 BedroomsSleeps 6Quick View
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    • Hot Tub
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    About this property
    Resort in Key Largo, located in the town of Tavernier, Florida, is at the southern tip of Key Largo island Enjoy a resort in southern Florida's subtropical zone, with easy water access, a hotel bar and restaurant, and fun Florida Keys town nearby. This location is keen for those who like to get out...
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    Key Largo, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 BedroomsSleeps 8Quick View
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    About this property
    Anyone can rent you their house, I provide a tropical resort with concierge services. This house has it all – a 7 min walk to Sombrero Beach, heated private pool, ocean views, a 'fisherman's' dock, high speed wireless Internet, etc., etc. Marathon recently spent $5M renovating Sombrero Beach -...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Professionally managed and tastefully decorated, this fully stocked Florida paradise is one of the most stylish vacation rental homes in the Keys! Whether you’re a fisher at heart looking for a getaway trip or a family seeking some down time in the sun, the Guitars & Tiki Bars home is equipped...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 BedroomsSleeps 8Quick View
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    About this property
    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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    2 Reviews
    2 BedroomsSleeps 6Quick View
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    • Patio
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    About this property
    Enjoy your getaway in Casa Solis, on the docks awaiting a gorgeous sunrise or a cool breeze at sunset on the deck. This brand new home provides the views and relaxing setting you are looking for! The two bedrooms and en-suite bathrooms are designed to perfection. Each room comes with its own LED...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Reviews
    3 BedroomsSleeps 8Quick View
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    About this property
    *** 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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    39 Reviews
    1 BedroomSleeps 4Quick View
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    • Satellite TV
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    Pet friendly
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    Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Downstairs is a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    12 Reviews
    2 BedroomsSleeps 6Quick View
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    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    About this property
    Welcome to DragonFly Lite our home in Marathon, FL in beautiful Florida the Keys, the house has 2 bedrooms a Queen in the master and a full size in the guest room, one bathroom, all the towels you will need for the pool or beach (please leave the sand outside). It’s our kitchen too, so there is...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In one of the most desirable locations in Key West, you will find the exquisite 2CoolFish. Located in Truman Annex. Just walking into this pristine home will take your breath away. Featuring two bedrooms and one and a half bathrooms, this home is perfect for a family or small group of friends...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Reviews
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    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs...
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Reviews
    4 BedroomsSleeps 12Quick View
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    About this property
    Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    1 Review
    3 BedroomsSleeps 11Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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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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    11 Reviews
    2 BedroomsSleeps 6Quick View
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    About this property
    One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby bars, shops, and fine dining....
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    About this property
    Our Tavernier family vacation home is like 'home away from home'. Property is fenced. Nicely decorated and tiled throughout our home is very well kept and clean only four homes from open Bay access with clear water canal and direct ocean access via Tavernier Creek. Master bedroom features queen...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Reviews
    3 BedroomsSleeps 8Quick View
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    About this property
    This house has everything! You can rent 1/2 or the whole house. The top unit has 2bd/ 2bths. Lower spacious unit has 1bd/1bth. Enjoy dinner on breezy upper or lower outdoor patios. This house is more convenient and offers much more than your ordinary 3/3. Each unit is very spacious, sleeps up to...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Reviews
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    About this property
    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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    3 BedroomsSleeps 8Quick View
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    12 Reviews
    2 BedroomsSleeps 6Quick View
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    About this property
    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    32 Reviews
    1 BedroomSleeps 4Quick View
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    About this property
    Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors. Key West Vacation Rentals...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    • Outdoor Dining Area
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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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    5 Reviews
    2 BedroomsSleeps 6Quick View
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    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    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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    6 Reviews
    1 BedroomSleeps 5Quick View
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    About this property
    Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer. Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This beautiful oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Family Vacation Rental Dwelling...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Welcome to our newly renovated, little slice of paradise! Come and relax at our beautiful Key Largo home, located on mile marker 87 in the Sport Fishing Capital of the World. Just minutes from John Pennekamp Park and the world...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Welcome to Paradise Point, a beautiful private community in sunny Key Largo! In this private and secure gated community of just 32 homes, paradise awaits you! In our home you'll be right on the water with a gorgeous view of a deep-water canal that has easy access to open water. We are located...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tropical paradise in Historical Tavernier, Florida, perfect for your family vacation! Conveniently located Oceanside at Mile marker 92.5, one hour drive from Miami. Easy ocean access and Tavernier Creek cuts through to the bayside just minutes south of our channel. Open plan living area is bright...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Elegant Florida Keys direct ocean access and some open water views from the dock and balcony. This property is a single family elevated home, the downstairs portion of the home is a storage facility. All rooms and bathrooms are upstairs. 40 foot dock with 4 cleats for two boats. A jet ski/boat...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
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    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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    SPECIAL SEPT. OCT. AND NOV RATES This renovated 4 bedroom 2 bath house is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Minutes from best fishing and diving in the world. Come to the...
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    Key Largo, Florida Keys 33170
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    MM 90 Beautifully Remodeled Home. This charming home is surrounded by mature trees making it very private, beautifully updated, offering 2 bedrooms 1.5 bathrooms (split floor plan), awesome screened in porch, car port, tons of storage, large kitchen pantry, balcony off from the main bedroom while...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    *** Owner is highly motivated to rent! Contact us for discounts *** This luxurious waterfront home is located on mile marker 106, on the ocean side of northern Key Largo (The Sport Fishing Capital of the World), near mile marker 105. Superb quality, beauty, and location, this house has it all!...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full vanity, and an open, spacious living room with beautiful furnishings....
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sorry, Not available Dec 1 2016 to April 3, 2017. Modern and attractive 2 BEDROOM, 2 BATH, CANAL-FRONT, Stilted Half Duplex Features : * Comfortable and cozy furniture and bedding + new bathroom * Centrally located in Marathon and 7 minutes to Sombrero Beach * 37 feet of deepwater dockage and...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    This tropically decorated 2 bedroom 2 bath unit, has a King bed and (2) Twins beds is approximately 1 hour and 20 minutes from Miami International Airport and 90 Minutes from Ft. Lauderdale airport.  Futura Yacht Club is located in the Village of Islamorada in the Upper Florida Keys. Located...
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    Tavernier, Key Largo 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    If you want peace and quiet and disconnect from the daily stresses of life, this is the place to be! Come enjoy all that the Florida Keys has to offer in this 'home away from home' Your reservation includes so many amenities! Great for a well-deserved get-away or Mini-vacation! Located in the...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    8 Reviews
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    Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture with a front...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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