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House Rentals and Vacation Home Rentals in Florida Keys, FL

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    1 / 24
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Key Colony Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Key Largo
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 24
    4 of 5 bubbles (16) Very good
    Islamorada
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 29
    Long Key
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Long Key, Florida Keys 33036
    1 / 60
    Key Largo
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    This Studio Apt has a beautiful Kitchen and Bath, tile floors, central zoned Air Conditioning and has views of Florida Bay open bay front. It is located in Kings Kamp RV Park at Mile Market 103.5 Bayside. We have a sandy beach, boat docks, marina, fish cleaning table, free Wi-Fi, free cable TV, and... View all property information
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    Key Largo, Florida Keys 33037
    1 / 11
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    The view, the view and THE VIEW! Ocean breezes to soothe and regenerate your soul. Expansive elevated patios, one screened as a Lanai and one open to the night stars. Just steps away is the immaculate pool and clubhouse where you can enjoy billiards, shuffleboard, tennis and meet friends at the... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 13
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    MONTHLY RENTAL ONLY This spacious 3 bedroom, 2 bath has all new stainless steel appliances and cabinets in kitchen, 15 ft. bar with wine cooler, new 55' flat screen in living room with cable TV. Large master bedroom with king size bed and French doors opening to pool deck plus 55' flat screen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (13) Very good
    Matecumbe Key
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada. Pass... View all property information
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    Matecumbe Key, Florida Keys 33036
    1 / 16
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This house is in a very quiet section of a quiet island . It is surrounded by palm trees. There is a large screened deck which catches the breeze. At the end of the canal (approximately a block ) you will be in a large open area between Big Pine and Little Torch ; from there you can easily travel... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
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    1 / 22
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    5 of 5 bubbles (2) Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Beautiful three story luxury home in the heart of Islamorada the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    4.5 of 5 bubbles (12) Very good
    Long Key
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside.  This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room.  The complex has 2 tennis courts, weight room, dockage, pool, fish cleaning station,... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 24
    Marathon
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Marathon, Florida Keys 33050
    1 / 21
    4 of 5 bubbles (37) Very good
    Key West
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 6
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Key West, Florida Keys 33040
    1 / 14
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Ocean Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    Two stories both bedrooms on second floor. Completely renovated. Beautiful quiet peaceful gated community on Florida Bay. 24 hour guard on duty. Completely renovated unit with state of the art appliances. Bathrooms beautifully professionally decorated with modern fixtures. Fully equipped kitchen... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 29
    4 of 5 bubbles (14) Very good
    Ramrod Key
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    • Porch
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    • Pet-friendly
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    • x
    About this property
    House and AMERICAN CARRIBEAN VILLA near to Key West, Florida in Ramrod Key, visit: www.villamarquesa.com for our Official Prices, Calandar and Photos and for our Sister Property Casa Serenity http://www.flipkey.com/ramrod-key-vacation-rentals/p300040/ See us in on TV as the most affordable rental... View all property information
    Location Information
    Ramrod Key, Florida Keys 33042
    1 / 5
    4.5 of 5 bubbles (2) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
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    • ?
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    • x
    About this property
    Relax in the Fabulous Florida Keys in your Tropical Bungalow! Two bedroom, 1.5 baths, very tropical atmosphere. Neat, clean, and comfy, with tile floors throughout. Smoking is not permitted! Easy access to the Gulf of Mexico from your 30' dock for world class diving, snorkeling, reef fishing,... View all property information
    Location Information
    Marathon, Florida Keys 33050
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    1 / 24
    Marathon
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Welcome to DragonFly Lite our home in Marathon, FL in beautiful Florida the Keys, the house has 2 bedrooms a Queen in the master and a full size in the guest room, one bathroom, all the towels you will need for the pool or beach (please leave the sand outside). It’s our kitchen too, so there is... View all property information
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    Marathon, Florida Keys 33050
    1 / 24
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
    Location Information
    Key Largo, Florida Keys 33037
    1 / 45
    5 of 5 bubbles (2) Excellent
    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 bubbles (33) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Gorgeous crystal clear, open water views of the Gulf of Mexico, incredible sunsets. Deep Water Dockage for your boat, snorkel, fish or dive right from the dock. This is not your typical canal home that are rented throughout Marathon. This one has open water, privacy and an un-obstructed view.... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 4
    5 of 5 bubbles (9) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Nestled behind hisbiscus and stands of bamboo Lone Palm welcomes you to a tropical oasis in the heart of Old Town. Located just a block off Duval at the corner of Truman & Simonton in Windward Park a gated community consisting of 13 privately owned homes around a sparkling 20 x 60 ft. pool; a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    Islamorada
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 28
    Tavernier
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully... View all property information
    Location Information
    Tavernier, Key Largo 33036
    1 / 23
    Islamorada
    Studio, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 26
    5 of 5 bubbles (21) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Yard
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    • x
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    • x
    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 11
    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    10 minutes to the OCEAN - DEEP WATER CANAL READY FOR LOBSTER SEASON!!!!! 3 bedroom 2 bath Stilt house on a canal. Nice screened in porch (mosquito proofed) to relax in the evening. 10 minutes to the Ocean!! Just 25 minutes to Key West. Walking distance to Looe Key Reef Resort and Tikki Bar... View all property information
    Location Information
    Ramrod Key, Florida Keys 330402
    1 / 17
    4 of 5 bubbles (1) Very good
    Key West
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 bubbles (1) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4 of 5 bubbles (16) Very good
    Key West
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    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. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • x
    About this property
    If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 52
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to your private balcony with great views of the property and Atlantic Ocean. The Owners are fishing enthusiasts as you will see when you relax in the comforts of home away from home.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    Summerland Key
    3 Bedrooms, 10 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    <BR><BR>Melody Key is probably the best kept secret in the magnificent Florida Keys. The Florida Keys are totally unique and the locals are probably the friendliest on the planet. The Keys are famous for their natural beauty and nature: One hundred and thirteen miles of overseas highway connects 42... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    1 / 12
    5 of 5 bubbles (1) Excellent
    Cudjoe Key
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Peace, Privacy, Perfect. This ocean front home has 180 degree wrap porch complete with patio furniture. Large 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. This home is spacious and well designed for comfort. Front room has 3 sets of double glass sliders... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 16
    Key West
    Studio, 6 Bathrooms, Sleeps 24 | Quick View
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    • ?
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    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (12) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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. Eaton Manor sits on the north side of LaBrisa and provides easy access to... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the... View all property information
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    Key West, Florida Keys
    1 / 27
    5 of 5 bubbles (5) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    La Dolce Vita is just steps to Duval Street! "La Dolce Vita" is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every room for a... View all property information
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    Key West, Florida Keys 33040
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    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (2) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 2 | Quick View
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    28 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    Islamorada
    Studio, 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 13
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half day, full day, and overnight sails. The yacht club has it's own private beach and... View all property information
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    Key West, Florida Keys 33040
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    Key West
    Studio, 2 Bathrooms, Sleeps 5 | Quick View
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    Key West, Florida Keys 33040
    1 / 24
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    Key West, Florida Keys 33040
    1 / 23
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (4) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the island. You have your own 17 foot boat for the entire week! HOW MANY PEOPLE CAN... View all property information
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    Marathon, Florida Keys 33050
    1 / 9
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Hot Tub
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    About this property
    1 bedroom with king bed. Living room with pull out sofa bed. 1 bath with jacuzzi tub and shower. Washer and dryer in unit. Balconies off of bedroom and living room with marina view. Stainless steel appliances. The Galleon has a heated pool with hot tub. A small private beach. Poolside tiki bar... View all property information
    Location Information
    Key West, Florida Keys 33040
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