Florida Keys Vacation Rentals

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MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early 1960’s and our neighbors tell us that at one time Jimmy Buffett’s manager owned and lived in the home. It has ...

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Minimum Rental: 28 Days "Casa Kai" has water views from almost every room in this home! Gaze at the water from your bedroom, the dining area, the balcony, or the Tiki! This home is so close to open water you almost feel like it is on the ...

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Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 10 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenitites and ideal location the ...

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Minimum Rental: 7 DaysSATURDAY to SATURDAY "Moon Bay A206" is calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. ...

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Minimum Rental: 7 Days"Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite ...

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Newly Remodeled 1 Bedroom 1 Bathroom, Marina, Pool, Paddle Boats, Kayaks, Tennis Courts, Bicycles. Fun and Sun. Great amenities, close to everything. Boat slips available on first come basis.Outdoor bar b q grills, great Sunsets from the Dock. ...

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This charming one bedroom cottage is the perfect hideaway.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find ...

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This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs ...

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Minimum Rental: 7 DaysLittle Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for ...

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Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.The downstairs living area is decorated in soothing cobalt and beachy ...

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Minimum Rental: 28 Days***** THIS UNIT IS CURRENTLY LISTED FOR SALE. WE ARE ONLY ABLE TO BOOK 1-2 MONTHS IN ADVANCE *****"Key Largo Yacht Club #8" is an exceptional 3 story townhouse located in a quiet oceanfront complex with heated ...

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Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located ...

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Barry Beach will take you back in time to the old Keys. The cottage was built in the mid 1960's, but has been beautifully renovated inside to accentuate island living at its best. With 4 bedrooms and 3 baths and 2000 sq. ft., the open floor plan accommodates ...

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Luxury private studio condo within Key Colony Beach ocean front complex. Condo features a full kitchen, heated pool and private beach with tiki huts, lounge chairs and BBQ grills for guest use. Our Condo has a full kitchen stocked with everything you ...

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Minimum Rental: 7 DaysLittle Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units ...

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Minimum Rental: 28 Days"Manatee Manor" is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal ...

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Minimum Rental: 28 Days"Matecumbe Jewel" is a jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting ...

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Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground ...

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Minimum Rental: 1 MONTH This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Everything you could want is located within the community - heated pool; hot tub; covered seating area; tennis court; children's ...

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Brand New Construction, 6 Bedroom , 5 Bathroom canal views, On the HIGHLY sought after Sombrero Beach !!! 100 Foot Deep Water Dock (my 23 foot boat sits in a lift so you get 65 foot to use) 10 minute ride through the famed Sisters Creek to the open ocean, ...

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Completely remodeled 3 bedrooms, 2 bath house in Marathon - the middle of the Florida Keys, on Mile Marker 51, only one hour to Key West. OUR WEEKS ARE SATURDAY - SATURDAY. Beautiful place in a quiet neighborhood. Direct access to the ocean, with 37 feet ...

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Walk the Beach! Beautiful 2 bedroom, 2 bath Ocean front condo at Coco Plum Beach Villas, nicely decorated and furnished. Leather recliners in the main living area overlooking the Atlantic Ocean. King in master, 2 twins in 2nd. Pull Out couch in living ...

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House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home ...

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Minimum Rental: 28 Days "Palm Harbor" is a spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full ...

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Duplex, 2 Bedrooms + Convertible bed (Sleeps 4-5), 2 baths, Wi-fi, all amenitiesGround level with back yard for BBQ and relaxing. Dock your own boat or a rental boat at this canal front home. Easy access from dock to the ocean or bay for fishing, snorkeling, ...

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MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master ...

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*****LAST MINUTE SPECIAL ***** RECEIVE 20% OFF MONTHLY RATE FOR ALL RESERVATIONS WITH AN ARRIVAL DATE BEFORE JULY 31, 2018Minimum Rental: 28 Days "Tropical Oasis" is an exceptional single family home designed for tropical living - charming ...

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Come enjoy the Beautiful Florida Keys! Outstanding property located in Key Largo in one of the most prestigious neighborhoods (Port Largo) 5 Bedroom 5 Baths 75 FT dock and davits, direct ocean access 2 miles 4400 SQ FT, two kitchens, gated, ...

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MINIMUM STAY: 28 DAYSFABULOUS BEACH HOUSE located directly on a mile long sandy beach. The original "Sea Grape" was destroyed by Hurricane Irma in September 2017. The decision was made to tear down and rebuild. The new Sea Grape is ...

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Minimum Rental: 28 Days"The Palms #314" is a sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's ...

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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 ...

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This recently remodeled and upgraded, this 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.Included at no ...

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"Too beautiful to put into words, this Oceanside five bedroom 7.5 bath house is a luxurious, yet comfortable place to get the most out of your Keys experience. Whether you are lounging in the heated pool or relaxing in the hot tub on the pool deck ...

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Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe ...

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This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. ...

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Sorry NO SMOKING or PETS!Ground level 4 bedroom, 2 bath waterfront home on a double lot with a saltwater pool with hot and cold shower, large pool deck and two Tiki Huts. 180 ft of waterfront and 90 feet of dock space with a double fish cleaning table. ...

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This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling Gear, Tennis Equipment, ...

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Minimum Rental: 28 Days"Casa Dorado" is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, ...

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Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of ...

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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 ...

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Minimum Rental: 28 Days"The Palms #405" is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings ...

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Minimum Rental: 28 Days "Twice the Charm" is a gorgeous newly remodeled single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from the dock which includes davits, ...

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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 ...

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Minimum Rental: 28 Days "Plantation Adventure" is a sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing ...

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This new gated Marathon home is 2 levels with an elevator. 3 Bedroom / 3 Bathroom , Sleeps 8 people, with all the comforts of home. This home offers nothing but the best in home furnishings and security. Panoramic water views from private decks off the ...

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Entering our luxurious condo, you will be impressed with expansive ocean views, literally from every room. Corner-sited and on the 1st floor (above parking), the wrap around private balcony, with all-new wicker lounge furniture, is but a stone toss to ...

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Minimum Rental: 28 Days"Lyons Landing" is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms ...

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Minimum Rental: 28 Days"Beacon Reef 501" is an exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen ...

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Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete ...

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'TEE BY THE SEA' vacation rental(we include 7 bikes free for our guests!!!)MY VAC. RENTAL SUSTAINED NO DAMAGE FROM HURRICANE IRMA. ITS DOING FINE AND READY TO ACCOMMODATE GUESTS. OUR CONDO COMPLEX IS FINE TOO AND WE ARE READY TO RECEIVE GUESTS. ...

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