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Florida Keys House Rentals

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    Travelers to Florida Keys are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1,323 Matching Rentals in Florida KeysView all 2,464 rentals
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    10 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    60 Waterways Drive1 / 26
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    About this property
    This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and ceiling fans...
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    Islamorada, Florida Keys 33070
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    This gorgeous waterfront home is a fisherman's dream with 65' of concrete dock, a covered fish cleaning station WITH a commercial ice machine, running water & outdoor shower - backyard shaded by palm trees. Located at MM90 oceanside right off Tavernier Creek with easy, quick ocean & bay access -...
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    Tavernier, Key Largo 33070
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
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    Welcome to this beautiful Tavernier, Florida vacation rental home to spend a fun filled or quiet vacation near the beach. This Tavernier canal home has a terrace from where you can sit and relax or sunbathe. All the bedrooms are designed and decorated for your comfort. The living room of this...
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    Tavernier, Key Largo 33070
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bayside Retreat. Pool, Boat and Beach1 / 13
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Porch
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    Island style, waterfront home with exclusive private white sand beach, A pool and protected dockage. 10 bedrooms, 8 bathrooms should be enough room for any size group.4 Living Rooms, Dining Room, Kitchen all have unsurpassed views of the open water and Sunset. On the first level is the pool. This...
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    Key Largo, Florida Keys 33037
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Brand New House in the Heart of the Florida Keys. Enjoy Paradise in this modern house that has every ones need in mind. 7 Room with 8.5 Bathrooms, fully equipped kitchen, Jacuzzi, pool, dockage for boats and more more much! The space Total of 7 Room with: 3 King beds 2 Queen beds 1 Full bed 2...
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    Marathon, Florida Keys 33050
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Our home is a 3 story in a private gated community. There is a private hot tub on the first floor along with a sitting area, dining area and grill. The roof is a great place for panoramic views of the gulf with a bar, dining area and lounge chairs. The second and third floors have balconies with...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Pelican House, is a 3 bedroom, 2.5 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the cooler seasons),...
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    Long Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Quick, easy access to Gulf and boating. Quiet location with privacy and beautiful views of the Gulf and nature preserve. Canoe or kayak from your dock to one of the locals' favorite snorkeling areas near the nature preserve. Offstreet parking and room for boat trailer. Free WIFI and DVR. one lot in...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Surround yourself with water views and canal-front convenience when you book your next stress-free getaway to this Key Largo retreat. Boasting views from nearly every window and private dock slipping into vacation mode will be a breeze. Set near the calm waters of Florida's Sunset Cove, and less...
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    Key Largo, Florida Keys 33037
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Sweet little home away from home. This 1 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 3rd floor balcony. If you are looking to get out on the water the complex...
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    Tavernier, Key Largo 33070
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Charming 3bedroom/2bath home in the Florida Keys1 / 19
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Dubbed Aguazul, the home has four bedrooms and three bathrooms. There's also a small bungalow off the pool deck, meaning the property can comfortably sleep nine. Two separate kitchens, one on each of the home's two levels, are another unique feature. Cool off in the home's oceanfront swimming pool,...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800 per...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bayside Bungalow1 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Cozy, i.e., small, but sweet efficiency bungalow. Clean. Great weekend retreat to enjoy fishing and diving with many places to choose from close by.
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    Key Largo, Florida Keys 33037
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    "Casa Manana," the name affectionately assigned this beautiful gated property in Summerland (Ramrod) Key, is a uniquely situated private waterfront venue. Enter through the gates and you will immediately be transported into the tranquil, easygoing and thoroughly relaxing Keys lifestyle. Located on...
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    Summerland Key, Lower Keys 33042
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    About this property
    Please note that this property has a 10AM check-out time. Quick Atlantic access, dockage, pool! 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...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Cozy, canalfront, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bedrooms are located in a separated, quiet part of the house, while the living, dining, and kitchen are open for enjoying each...
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    Long Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    About this property
    If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sweet little home away from home. This 2 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 4th floor balcony. If you are looking to get out on the water the condo...
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    Tavernier, Key Largo 33070
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Sit back and relax in this delightful home, situated on the open water. The entire rear wall of this home is glass for endless views of the blue-green waters of the Florida Keys. Equipped with all the comforts of home plus a heated pool. The open porch catches the breeze, and the tropical setting...
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    Ramrod Key, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Central Heating
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    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    My place is water front, located near John Pennekamp state park which offers boat, snorkeling and scuba tours. You’ll love my place because of the views and lovely location, This house is perfect for couples, business travelers, and families (with kids). If you choose to bring your own boat, jet...
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    Tavernier, Key Largo 33037
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Fill your days with luxury and relaxation when you book your stay at this top-notch Long Key home. With a swim-up bar, a private pool, a hot tub, and a private beach, you won't have to go far for fun. Two-and-a-half miles from Layton, and 14 miles to Marathon, this quiet neighborhood is the perfect...
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    Long Key, Florida Keys 33001
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    This  newly renovated and remodeled 2 Bedroom Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' This unit is comfortably and stylishly furnished, it has(2)...
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    Tavernier, Key Largo 33070
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Enjoy a getaway in one of Islamorada's most prestigious neighborhoods when you rent this three-bedroom, three-bathroom home. Located at the end of a cul-de-sac within the Port Antigua neighborhood on Lower Matecumbe Key, the home quickly enchants arriving guests with its peach-colored exterior set...
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    Long Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    HISTORIC KEY WEST  - Main House - Sleeps 101 / 23
    (4)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of ten (10) guests - (1) queen bed, (1) full bed, (1)...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This is a WEEKLY RENTAL! Welcome to Sunset Bay, where you’ll experience the most glorious sunsets! Located on tranquil Big Torch Key, Sunset Bay is situated on the open water of Niles Channel, Gulf side. This home is an outdoor lover’s delight! Situated on a large parcel with a long grassy...
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    Ramrod Key, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation. Great Gulf-side boating is at your fingertips and just a short run out to the Atlantic to fish and dive all the great reef spots. The gulf side waters are full...
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    Little Torch Key, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Cottage is located in a Gated Estate on the Gulf of Mexico in the Florida Keys for watching those beautiful Keys Sunsets !!! 'Tiki Palm Cottage' has it's own private Tiki hut for relaxing with a cool beverage or just for reading a favorite novel. Walk in through double French doors to a large...
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    Tavernier, Key Largo 33070
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Keys has to offer. This home offers 70 feet of canal...
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    Little Torch Key, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Relaxing Getaway (REDUCED) in Key Largo1 / 7
    (9)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Our Key Largo Holiday Vacation Rental home is fully air conditioned and all on one level with Tiled floors for hygiene throughout. We have a Queen size bed in the master bedroom, 2 x full size doubles in the second bedroom. All beds have quality posture-pedic mattresses. Soft furnishings such as...
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    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy ride under some bridges to Pine Channel with decent...
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    Lower Keys, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Architects Cottage on Quiet Lane in Old Town1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Everyone wants to leave their worries behind and escape on a soothing beachfront vacation - why not make your next one something special? This top-floor Long Key condo has it all: a gorgeous white sand beach, a shared swimming pool with a swim-up bar, and an amazing selection of games and...
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    Long Key, Florida Keys 33001
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    This Cozy one story tropical and enchanting house sits on 100 ft wide salt water canal and about 100 yard from the warm water of the Atlantic ocean, it's on the junction of the Tavernier creek which takes you either to the Atlantic Ocean or to the Bay, it has 3 bedrooms and 2 bathrooms and can...
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    Location Information
    Tavernier, Key Largo 33070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Satellite TV
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    Escape to the sunny Florida Keys with this nautically themed Marathon vacation rental! Complete with a private deck and boat launch, this charming duplex is the perfect antidote to beat those winter blues. Boat-lovers will adore this home's canal-front location, which has its own private boat...
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    Location Information
    Marathon, Florida Keys 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Mobile Home in Venture Out Sleeps 5 Mile Marker 231 / 22
    (9)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Hot Tub
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    Cute and CozyMobile Home located in gated community of Venture Out MM 23 in the Florida Keys. 2 bedrooms and 1 bathroom on a dry lot along the fence. Fully equipped kitchen, newer refrigerator , self cleaning oven, free internet, Cable, 50 inch flat screen TV in living room 4 A/C's 2 queen...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Located at MM 73 in Lower Matecumbe, Islamorada - this 3 bedroom and 2.5 bath will sure to be your home away from home.  Nicely decorated and very comfortable.  You can sit outside in the hot tub and enjoy the peaceful canal.  Great home for your next vacation. Near the house is the small Anne's...
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    Location Information
    Long Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (49)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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