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Florida Keys Villas

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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 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    PALMS 3141 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    KEY LARGO YACHT CLUB 81 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Minimum Rental: 28 Days "Key Largo Yacht Club #8" is an exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates a boat...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled in 2014/15 so everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! A brand new luxury heated pool / spa was added in 2015 and is surrounded...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Luxury 1 Bedroom with Full Kitchen - Sleeps 3 - Walk to the Beach & Nightlife1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    THE MARTHA SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    About this property
    Enjoy a little European elegance combined with Florida Keys Charm at this Lower Matecumbe Key oceanfront property.  The main home has four bedrooms and 4.5 baths.  A separate bungalow contains a king suite with kitchenette, as well as its own patio overlooking the Atlantic.  Spend your vacation...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Conch Condo1 / 23
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    CONCH CONDO -- A two-bedroom, two-bath condo in Truman Annex. This second-floor condo features fully equipped kitchen, two full baths, top-quality custom furniture, plasma televisions and home theater in living room, plasma televisions in both bedrooms, soaring cathedral ceilings with ceiling...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tamarind Bay Club is a quiet private gated complex on the beautiful Blackwater Sound in Key Largo, Florida. Located on US Highway 1 between mile marker 104 and 105. It is a 1.5 hour drive from Miami South Beach and 2.5 hours from Key West. Tamarind Bay is conveniently located within walking...
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    Tavernier, Key Largo 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Havana Lane: A classic conch cottage with rustic charm1 / 25
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally located...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    An adorable 2 bedroom and 1.5 bath condo at Summer Seas.  The condo has everything that you need to make sure your stay is very comfortable.  The complex is located right on the bay and has amazing sunsets. Additional amenities include: airbnb rounding adjustment.
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    Tavernier, Key Largo 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Full Kitchen Weeks are Friday to Friday and Saturday to Saturday only Welcome to a haven in the Florida Keys! Indigo Reef is located in Marathon, in the heart of the Florida Keys only 90 miles south of Miami. Experience an incomparable Keys vacation in one of the unique waterfront Villas. The...
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    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This Entire Home, a 3 Bedroom/2 Bathroom vacation hideaway will be yours! My place is just a few hundreds yards away from John Pennecamp State Park, one of the most popular tourists destinations in the Florida Keys. It's ideal for a day at the beach and water sports! You’ll love my place because...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Garden1 / 23
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Ocean Views
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    Magnificent Gulf Front Pool Home Offers the Perfect Location for beautiful sunsets! Amenities include 3 Bedrooms, 2.5 Bathrooms, Sparkling Fresh Water Pool, Panoramic views of the Gulf of Mexico, Deep Water Dockage and Carport for Parking. Home is situated right on the Vaca Cut offering ideal...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Finn Key1 / 24
    (32)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    FINN KEY: A beautiful 2 bedroom 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking distance to the Duval Street...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    LAST MINUTE DISCOUNT! 48' 4 Bed 4 Bath Yacht1 / 17
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Take it out for a snorkel or sunset cruise. Breath taking views from your kitchen window.
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    SUNSHINE PLACE1 / 23
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Minimum Rental: 7 Days "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Brand New 4/3 Pool Home on Canal near lagoon1 / 23
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    4/3 villa in Marathon, FL that has what you are looking for. It's a Brand New unit that has was professionally decorated.The spacious layout is more than 1,700 square feet and can house a large family. It has a fully equipped luxury kitchen with stainless steel appliances, granite in the kitchen...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tucked away near the Southernmost Point, Louisa's Hideaway is it!1 / 12
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything. Just furnished in 2012 with the finest tropical decor, flat screen TV's, wireless internet and top of the line gourmet kitchen. The large living area is spacious and cheery with tall...
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    Little Torch Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Artist Garden1 / 24
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Relax in this 3 bedrooms 2 bath Ocean Front home. This property is right on the ocean, with a 40' dock. No canals or neighbors to block your view. No elevators or parking garage. Just park your car and step to paradise. It's in close proximity to hospital, pharmacy, supermarket, gas station,...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sailor House--Newly Renovated 2BD/1.5B steps off Duval St.1 / 18
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave about their tropical “home away from home.” Its...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southard Comfort: Historic Old Town and Seaport, Private Pool & Parking1 / 32
    (13)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    “Southard Comfort” is true Island living in downtown Historic Old Town Key West. Two story, 3 bedroom, 2.5 bath plus outdoor shower Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pack your bags!  We've got the perfect vacation home for you and your family!  This adorable 3 bedroom/2 bath home is located on a deep water canal at the 74 mile marker Bayside.  Great yard with room for your boat trailer!  All 3 bedrooms are on one floor.  House is stilted.  Screened porch on...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Hot Tub
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    About this property
    1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths Elegant sophistication abound in this fabulous 2 bedroom 2 bath ocean-view condominium at the premiere 1800 Atlantic Condominiums. This property has been totally renovated and no attention to detail has been spared. Tommy Bahama...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Slip into the beach lifestyle and leave the daily grind behind when you book your stay at this oceanfront Layton cottage. With a dock, expansive deck, and a stunning beach location, you may never want to leave. With historic roots as the home to the 1900's author, Zane Grey, and easy access to a...
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    Long Key, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine. Just minutes from Cudjoe Gardens marina for gas, bait and your fishing needs. Deep draft boating will accommodate up to 4 foot draft. Large and spacious inside with open...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 2141 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Minimum Rental: 28 Days "The Palms #214" is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Enjoy this large oceanfront home on Summerland Beach. This expansive 3 bedroom, 2 bathroom home is just perfect for large families and big boats. Over 2,500 square feet of living space with lots of room for everyone to spread out. The kitchen has plenty of room for everyone to get in act to make...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    MY PARADISE1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Bahia Azul, 'Bay of Blue' is exactly the perfect spot for your next Florida Keys adventure. The open water views are just stunning and spectacular. Its location at the end of the street makes this a very private get-away. This large home will accommodate all your friends and family with 4 bedrooms...
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    Ramrod Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Tarpon House is a spacious, stylish, colorful, beachy, updated home an almost an acre of land in the heart of Marathon, Florida Keys. It features 4 bedrooms with king size beds and 32" flat screen TVs. The living room has a 60" flat screen with cable. There is WiFi at the home as well. A...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Key West Crown Jewel1 / 24
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    KEY WEST CROWN JEWEL -- We know that you will enjoy staying in our vacation rental condo Key West - our little bit of Paradise. This is a 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space and vaulted ceilings. Enjoy absolutely breathtaking ocean views and the colors of...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 2 Bedrooms with king size beds, 2 Bathrooms, and a third guest room/office/ with gym equipment. Charming 2 story conch house on a quiet street in Old Town, right between Duval and Higgs Beach! Easy access to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Great Waterfront FL Keys Homes - 1 Low Price1 / 26
    (12)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Pet friendly
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    Relax and enjoy your vacation with a specatacular waterfront view - look out over a crystal clear lagoon out onto the Gulf of Mexico. This full duplex Waterfront Home with 75' of deepwater dockage, 4 Bedrooms and 4 Baths is great for large groups looking for a quiet place to relax, fish, kayak and...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Large Waterfront Sombrero Luxury Home/w Boat Dock1 / 24
    (1)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Patio
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    Great for families or several couples! Exquisite 7 bedroom 5 bath, single family home in the desirable Sombrero neighborhood just minutes to the beach. Downstairs outdoor living, balconies on both levels with porch area, deep water dockage with access to ocean and gulf. This magnificent home offers...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    New 4 bedroom,4bath in Beautiful Key Colony Beach1 / 21
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    New 4 bedroom, 4 Bath duplex. This beautiful new home has a private pool, a dock- 2 10 by 30 decks on the channel. The dock is 37 1/2 ft. There are 2 refrigerators, bait freezer, fish cleaning table, 2 bicycles. All bedrooms have flatscreen TV's. The family room also has a queen sofa bed. 3 of the...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    PALMS 4171 / 25
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Minimum Rental: 28 Days "The Palms #417" has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Minimum Rental: 28 Days "Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This is a...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pelican Landing Florida Retreat1 / 23
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy the unobstructed open water view from anywhere on this acre-sized, Gulf-front estate. Enjoy fruiting palm trees, a private hot tub, pool, a boat ramp, and, coming soon, a private dock, which will be available for all 2018 rentals! This home is very private and still part of Marathon. This...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lavender Jungle1 / 24
    (25)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo for rent Key West located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a large brick patio and grill. Master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Dreaming of an awesome Florida Keys vacation? This is your perfect pick! This Cudjoe Key home has everything you could wish for and a perfect vacation spot! The home is designed with rich and warm wood tones making it the perfect place to relax after a long wonderful day of fishing and diving in...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    CONCH BAR SOUTH1 / 24
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Minimum Rental: 28 Days "Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family home...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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