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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 27
    4 of 5 stars (1) Very good
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 22
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 20
    5 of 5 stars (6) Excellent
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 25
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
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    Islamorada, Florida Keys 33023
    1 / 22
    Key Largo
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Waterfront Condo rental includes HD Comcast Cable on 2 New Samsung LED 3D HDTVs (55' & 32'), WiFi, Electric, Water, Parking, 36' Boat Slip on the seawall behind the condo available upon advance supply of registration/insurance doc approval, and an Airport on the club grounds. Personal Golf Cart for... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 12
    4.5 of 5 stars (13) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    Key Colony Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our unit is a two bedroom, two and one-half bath, washer/dryer, and private balcony with spiral staircases leading into the courtyard. We are an Oceanfront condominium with our own private beach, beautiful heated pool, tiki hut on the beach, and Oceanfront deck that can be reserved for private... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 10
    5 of 5 stars (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    <BR><BR>Luxurious direct bayfront townhome with dock, upgraded unit.<BR><BR> best location in the 50's overlooking large green yard and open bay with slip in front.<BR><BR>3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 17
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Please call or email to inquire about specific dates. We can be accommodating depending on your dates and needs. Come experience the Keys vibe the way locals do it. This cute, cozy and totally remodeled mobile home is located in the heart of the Keys. It is close to everything (shops,... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • x
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    About this property
    Resort in Key Largo, located in the town of Tavernier, Florida, is at the southern tip of Key Largo island Enjoy a resort in southern Florida's subtropical zone, with easy water access, a hotel bar and restaurant, and fun Florida Keys town nearby. This location is keen for those who like to get out... View all property information
    Location Information
    Key Largo, Florida Keys 33070
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    1 / 27
    5 of 5 stars (52) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Outdoor...
    • Terrace
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    About this property
    SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security. Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an open and airy feeling and is one... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    5 of 5 stars (3) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • x
    About this property
    Welcome to "SANDY BEACH" in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 12
    5 of 5 stars (2) Excellent
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our property, private deep water canal dockage. This beautifully decorated home also offer two Association parks with beaches, pavilions and two private boat ramps. Shopping and fine dining nearby. Easy ocean and back country fishing from our back yard. Key west is a short scenic hour and half... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 9
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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    • x
    About this property
    Neat, clean and perfect for a family vacation. This 2 bedroom, 2 bathroom home sits on a wide, deepwater canal Comfortable beds and furniture. Plenty of parking and room for a boat trailer onsite Optional access to a pool at the Glunz Ocean beach club $12 per person per day Outside Covered... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 46
    4.5 of 5 stars (10) Very good
    Matecumbe Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at... View all property information
    Location Information
    Matecumbe Key, Florida Keys 33036
    1 / 20
    Long Key
    3 Bedrooms, Sleeps 6 | Quick View
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    • Porch
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    • x
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    • x
    About this property
    Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish cleaning station, and free Wi-Fi... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 27
    Tavernier
    6 Bedrooms, 4 Bathrooms, Sleeps 21 | Quick View
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    • x
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    About this property
    Truly a dream in the Keys. Right on the Ocean, Key largo Sound. View Beautiful sunrises from the balcony that wraps around the back of the house. Fish from the 60 foot waterfront cement dock. Enjoy Scuba diving or Snorkeling from the local tour companies. Laze by the pool and grill the fish you... View all property information
    Location Information
    Tavernier, Key Largo 33037
    1 / 20
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Balcony
    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 23
    Marathon
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Waterfront
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Ocean Views
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Home sits on a large (200’+), quiet lagoon on the Gulf side. We have 2 MASTER BEDROOMS, one upstairs and one poolside (newly remodeled with King bed and new large custom shower), as well as a guest bedroom upstairs. The 42” High Def TV comes with 150+ Satellite channels and FREE HBO. The two wrap... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 16
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    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... View all property information
    Location Information
    Marathon, Florida Keys 33050
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    1 / 27
    4.5 of 5 stars (25) Very good
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    • ?
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    About this property
    BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • x
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    • x
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    3.5 of 5 stars (10) Average
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Secure Parking
    • Hot Tub
    • Children's Pool
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    • Pet-friendly
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    • x
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    • x
    About this property
    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... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 8
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
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    • x
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    • x
    About this property
    Very private on a quiet street where the neighbors are kind and helpful. A half mile to an award winning beach, Sombrero that you can bike or walk to, If you don't want to go by car. Lit bike, walking path take you into town which is a half mile away. Grocery store, Walgreens and Kmart as well as... View all property information
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    Marathon, Florida Keys 33050
    1 / 18
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    This beautifully furnished and newly renovated condo is airy and offers all the comforts of your own home. Walk in to a spacious living room with an adjacent dining area and then onto a full kitchen with everything necessary to prepare and serve your meals. The kitchen has granite counter tops, a... View all property information
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    Marathon, Florida Keys 33050
    1 / 10
    Big Pine Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    About this property
    OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 28 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quiet relaxing neighborhood.... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 4
    5 of 5 stars (2) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Ocean View Cottages (3) Sea Horse, Horse, Periwinkle 2 bedroom - 2 bath These are ocean view cottages perched in the air 12 feet on pilings open to fabulous views. With a full gourmet kitchen and great attention to detail, this cottage has a warm feel at home ambiance. Kick back and enjoy the... View all property information
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    Marathon, Florida Keys 33050
    1 / 54
    Cudjoe Key
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
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    • ?
    About this property
    Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size Sleep Number Bed - Fully... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 31
    5 of 5 stars (23) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen televisions, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 14
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    <b> Minimum Rental: 1 Month </b> Comfortably furnished and ready for you. 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, or watch the spectacular sunsets over the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 16
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
    • ?
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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
    1 / 14
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Our property, private deep water canal dockage, and underwater lighting. These beautifully decorated homes also offer two Association parks with beaches, pavilions and two private boat ramps. Shopping and fine dining nearby. Easy ocean and back country fishing from our back yard. Key west is a... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 18
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    4.5 of 5 stars (5) Very good
    Duck Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Private residence on Duck Key. 2 bedrooms and 2 baths upstairs with a seperate one bedroom one bath apartment downstairs. Apartment has own kitchen and family room. Private dock with heated pool. Ocean kayak and fishing rods included. Catch tarpon right off the dock. House extensively... View all property information
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    Duck Key, Florida Keys 33050
    1 / 16
    5 of 5 stars (6) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 bedroom, 2 bathroom Ocean Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2013. It has dockage for boats up to 50 feet. This Villa is 20 feet from the Ocean and has a private beach 50 feet from the patio. We provide a golf cart, Kayaks, fishing equipment, tennis... View all property information
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    Key Largo, Florida Keys 33037
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    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    This is a Duplex 1 bedroom apartment located in Kings Kamp RV Park which has a Marina, Docks, Beach and magnificent sunsets. Tile Floors, air conditioned, cleaned, freshly painted. We have Staff on property daily and there is a coin laundromat for your convenience. Located across the street from... View all property information
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    Key Largo, Florida Keys 33037
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    Marathon Shores
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    This private vacation home is situated at a great location close to the middle of Marathon with just a lovely short walk or bike ride to the famous Sombrero Beach. 6 bedroom/ 3 bathroom with comfortable and inviting coastal designed decor. Attention to detail with fine linens and beach towels. 2... View all property information
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    Marathon Shores, Marathon 33050
    1 / 12
    5 of 5 stars (1) Excellent
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
    About this property
    "Welcome Aboard" as we say here at Mangrove Marina, located in the northern end of Islamorada in Tavernier at Mile Marker 91.7 on the Bay side in a protected tranquil oasis cove of the beautiful Florida Keys. Our 'Aqua Lodges' are a boat lovers dream with all the comforts of home, including a full... View all property information
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    Tavernier, Key Largo 33070
    1 / 24
    3.5 of 5 stars (3) Average
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • x
    About this property
    Half duplex located in prestigious Key Colony Beach. Tropical decor throughout. Located on a 100ft. wide canal with quick access to ocean. There is a concrete dock for your boat, and a great patio in the back. You are within walking distance to the "Cabana Club" , a private beach club with a... View all property information
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    Key Colony Beach, Florida Keys 33050
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    Key West
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    5 of 5 stars (1) Excellent
    Long Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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 bed rooms 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
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    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
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    • x
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    Newly Renovated Condo, Canal Front. Walk To Shopping, Restaurants & Golf. 1 Bedroom, 1 Bath, Sleeps 2 non smokers only! One of the best unit in the complex, end unit, across the street from golf course. Unit is fully furnished. Short distance from the beach and attractions. Wonderful view on... View all property information
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    Marathon, Florida Keys 33050
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    Summerland Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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    Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished... View all property information
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    Summerland Key, Lower Keys 33042
    1 / 28
    5 of 5 stars (1) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    Great 2/1 house. Completely renovated. Full kitchen with new stainless steel appliances: Microwave, Range/Oven, Dishwasher, Refrigerator. Central A/C & Heat. Master bedroom has queen size bed and a 32" flat screen tv. Second bedroom has a full size bed and a twin size trundle (full sleeps 2 and... View all property information
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    Key Largo, Florida Keys 33037
    1 / 26
    5 of 5 stars (2) Excellent
    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
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    Tropical paradise in Historical Tavernier, Florida, perfect for your family vacation! Conveniently located Oceanside at Mile marker 92.5, one hour drive from Miami. Easy ocean access and Tavernier Creek cuts through to the bayside just minutes south of our channel. Open plan living area is bright... View all property information
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    Tavernier, Key Largo 33070
    1 / 11
    Key Largo
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
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    • x
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    • x
    About this property
    Newly remodeled split level townhouse in luxurious Mariner's Club Private Resort. 3 bedroom, 3 1/2 bath with sleeping accommodations for up to 8 guests. Unit is a 2 bedroom/2 1/2 bath + 1 bedroom/1 bath efficiency with kitchenette. Balconies with seating on 1st and 2nd floors. Great amenities... View all property information
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    Key Largo, Florida Keys 33037
    1 / 13
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
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    Key West, Florida Keys 33040
    1 / 11
    5 of 5 stars (1) Excellent
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    'Welcome Aboard' as we say here at Mangrove Marina, located in the northern end of Islamorada in Tavernier at Mile Marker 91.7 on the Bay side in a protected tranquil oasis cove of the beautiful Florida Keys. Our 'Aqua Lodges' are a boat lovers dream with all the comforts of home, including a full... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 50
    5 of 5 stars (14) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
    • ?
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    • x
    About this property
    $1,500 (Standard Rate for 2016) - additional rates apply to holidays and Lobster Weeks.ASK ABOUT REDUCED FALL RATES! (September 2016- December 17, 2016) Reduced rates do not apply to holiday weeks. PRIVATE-ON-SITE POOL, 45 FT DOCK, CABANA CLUB, GROUND LEVEL, CARPORT, W/D, BAIT FREEZER,OUTSIDE... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051