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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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    4.5 of 5 bubbles
    14 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    5 of 5 bubbles
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    3 Bedrooms, Sleeps 8Quick View
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    About this property
    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4.5 of 5 bubbles
    23 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    6 Reviews
    1 Bedroom, Sleeps 4Quick View
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    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving....
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    9 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    About this property
    When you arrive, you know you've come somewhere very special. This condo has the most spectacular views of the the Atlantic Ocean and a pristine heated pool. Located on Coco Plum Beach in Marathon, Florida Keys, you're in a secluded yet central base for all Keys sightseeing and activities, if you...
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    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    3 Reviews
    1 Bedroom, Sleeps 4Quick View
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    About this property
    Down stairs apartment with King size bed and Queen Sofa bed. Boat dockage available with this unit. Very nice place. If your looking for a party pad this is NOT it. Very quiet neighborhood. Outside bar and tables available to use. Also a gas grill is available. If you bring a boat a 32 ft is...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    8 Reviews
    Studio, Sleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    4 Reviews
    3 Bedrooms, Sleeps 10Quick View
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    About this property
    Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4.5 of 5 bubbles
    2 Reviews
    Studio, Sleeps 3Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    Comfortable studio condo with full kitchen and a full size pull-out couch for extra guests. This condo has full resort amenities from a marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables and charcoal grill, along...
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    Marathon, Florida Keys 33050
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    4.5 of 5 bubbles
    15 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    11 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled 1,200 + square footage home in the Bayhaven Community. This house has a master bedroom very tastefully decorated as well as a second bedroom with full/twin bunk bed, and a queen sleeper sofa in the living room. Open layout allows you to cook, eat and relax while spending quality...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    5 of 5 bubbles
    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    • Ocean Views
    • Balcony
    • Satellite TV
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    • Terrace
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby....
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent 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 33023
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    Smoking allowed
    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    7 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    2 Reviews
    3 Bedrooms, Sleeps 7Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    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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    2 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a dip in our gorgeous new pool, or jacuzzi (for 14 people)! Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private gatehouse and road. The suite offers a...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    About this property
    In the heart of tropical key largo, Port Largo Villas has an atmosphere of a 5 star resort with its own sandy beach and within walking distance to Marina Del Mar (305.451.4107 call Dock Master to reserve slip). For the water enthusiasts, it doesn't get any better for sportfishing, diving,...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    2 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropical setting. The living...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    3 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4.5 of 5 bubbles
    3 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    21 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    Smoking allowed
    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute walk away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.5 of 5 bubbles
    5 Reviews
    1 Bedroom, Sleeps 4Quick View
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    • Balcony
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    • Porch
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    Pet friendly
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    About this property
    This is a beautiful home, you will enjoy every minute of your stay here! There aren't many homes built like this in the Keys. The room for rent is the guest room (the other room is occupied), with 14 foot vaulted ceilings, a comfy, queen sized bed and a ladder leading to a crawl space above (see...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4.5 of 5 bubbles
    13 Reviews
    1 Bedroom, Sleeps 3Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee...
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    Islamorada, 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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    • Wi-Fi
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    • Secure Parking
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    • Private Garden
    • Ocean Views
    • Washer
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking to vacation in the beautiful keys? Our spaceous 950sq ft. Home is conveniently located close to many of the things the keys has to offer! After enjoying a fun filled, sun soaked day come home kick back and relax at our little piece of paradise. Our beautifully decorated beach theamed home...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    5 Reviews
    1 Bedroom, Sleeps 4Quick View
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    About this property
    Situated on at natural Key's sandy sunning beach a scant few feet from the water's edge looking out to the Atlantic Ocean you'll find three of the most enchanting "honeymoon-type" Cottages in the Florida Keys. Made from Dade County Pine with vaulted beam ceilings these beach bungalows offer...
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    Marathon, Florida Keys 33050
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    2 Reviews
    Studio, Sleeps 2Quick View
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    About this property
    Our charming efficiencies are located 50 yards from the Atlantic Ocean. All units are fully furnished with well-equipped kitchens, linens, and baths. Each efficiency has a small outdoor space that share a tropical front yard with individual gas-BBQ grills, and picnic tables with umbrella's for...
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    Grassy Key, Marathon 33050
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 of 5 bubbles
    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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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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    • Ocean Views
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    • Waterfront
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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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    4 Bedrooms, Sleeps 10Quick View
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    Pet friendly
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    About this property
    Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action! Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4.5 of 5 bubbles
    3 Reviews
    Studio, Sleeps 2Quick View
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    ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off by...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 of 5 bubbles
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    Part of Southernmost Sanctuary Suites The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    4 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home is locate in Key Largo "Diving Capital of the World." Key Largo is the first island of the Florida Keys, south of the Florida mainland. The house has three wonderfully decorated...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    5 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    <BR><BR>Luxurious direct bayfront townhome with dock, upgraded unit.<BR><BR> best location in the 50's overlooking large green yard and open bay with slip in front.<BR><BR>3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    25 Reviews
    1 Bedroom, Sleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
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    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! The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4.5 of 5 bubbles
    5 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    This fully furnished 4 Bedroom, 3 1/2 Bath Canal Front Home is the ideal Escape to Paradise. One thing that cannot be seen through photos is the amount of privacy this location has, at the end of the Cul-de-sac with the canal and mangroves surrounding the home. Double Boat Dockage, Large Tiki Hut...
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    Key Largo, Florida Keys 330037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Children's Pool
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    • Private Garden
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    There is room for the whole family in this 2,200 sq. ft. townhouse with In-Laws quarters. As you enter the first floor you will find an open floor plan with living room, full bathroom and kitchenette with microwave, toaster, coffee maker, portable induction single-burner cooktop, and refrigerator....
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    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 of 5 bubbles
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    2 Bedrooms, Sleeps 6Quick View
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    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    27 Reviews
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    Hibiscus Hideaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St. Welcome to the perfectly located and affordable apt Hibiscus Hideaway. You will not find a better spot to spend your sunny days and exciting...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    • Balcony
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    Pet friendly
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    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tucked away on a gated tropical estate, is our 'Island Breeze Cottage'. This cottage is located in the middle of the Estate and steps away from our white sandy beach and those beautiful Gulf of Mexico sunsets !! There is a tiki hut on the beach. And a dock to fish from or go snorkeling right from...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 of 5 bubbles
    1 Review
    2 Bedrooms, Sleeps 8Quick View
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    About this property
    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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    4.5 of 5 bubbles
    13 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Terrace
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    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    42 Reviews
    1 Bedroom, Sleeps 4Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful condo is newly remodeled and located on the 2nd floor with elevator access. The Balcony overlooks Marina and Atlantic ocean with Spectacular views. The master bedroom has a king bed, cable TV with VCR and DVD. The guest bedroom has twin beds. The kitchen is fully equipped, including...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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