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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 14
    4.5 of 5 stars (3) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 22
    3.5 of 5 stars (10) Average
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 brand new A/C's 2... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 25
    4.5 of 5 stars (6) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights (Saturday to Saturday)</b> BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
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    Islamorada, Florida Keys 33070
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Central Air Conditioning. This apartment is in the same building that has our office adjacent to it. This is a beautiful apartment. TV with 75 channels, linens, central air, brand new bathroom with all new fixtures and brand new kitchen. Our price has no hidden additions-just sales tax. The... View all property information
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    Key Largo, Florida Keys 33037
    1 / 20
    5 of 5 stars (1) Excellent
    Marathon
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Unit 8c is an efficiency in a tri-plex located about 50 yards from the Ocean. It has a queen size bed, futon sofa and a small dining table with 2 chairs. The efficiency has a medium size kitchen with sink and medium size refrigerator, four burner stove. It also has a private bath with toilet, sink... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 15
    5 of 5 stars (2) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    <b> Minimum Rental: 7 Nights SATURDAY to SATURDAY</b> 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. World famous dive sites are minutes away and phenomenal fishing is... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 17
    4 of 5 stars (1) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of... View all property information
    Location Information
    Key West, Florida Keys 33040
    Marathon
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The Cats Eye has a queen bed in the bedroom and a sleeper sofa in the living/dining room. Cable color TV, A/C, paddle fans and full kitchen. BBQ grill. Light and bright. Recommended for 2 but will accommodate 4 people including children. View all property information
    Location Information
    Marathon, Florida Keys 33050
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    1 / 16
    Grassy Key
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Imagine gazing across a large, sparkling swimming pool to see a natural in-ground aquarium..... Big enough to swim in and filled with tropical fish. The dock accommodates large boats drawing 5' + The home sits on almost 3 acres of landscaped property The house is large and can handle big groups... View all property information
    Location Information
    Grassy Key, Marathon 33050
    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 / 9
    4 of 5 stars (1) Very good
    Key Largo
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2 bedroom, 2.5 baths, sleeps 6, Townhouse<BR><BR>Beautiful, recently remodeled, 2 bedroom, 2½ bath townhouse in gated, bayside community. Fully equipped with everything you need to enjoy a great vacation in this tropical island paradise. Heated swimming pool, toddler pool, marina, boat ramp,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 28
    5 of 5 stars (5) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This truly tropical retreat Keys’ home has an open floor plan, vaulted ceilings, and modern open kitchen. Master Bedroom has king sized bed, full bathroom with shower, granite sink, walk in closet, glass block windows. Second Bedroom has queen sized bed, closet, and adjoining bathroom with... View all property information
    Location Information
    Marathon, Florida Keys 33417
    1 / 24
    5 of 5 stars (1) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    2 bedroom, 1 1/2 bath condominium in wonderful, private Buttonwood Bay Condominium Association, Bayside, Key Largo FL. Extended porches, paved rear deck complete with rocking chairs to enjoy the sunset. Peaceful spot, end unit with private side yard. House tiled throughout. 15 steps to the water.... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 24
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Duplex in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait and tackle shop, bank, jewelry store, and much more. Two marinas that you can use, rental of jet skis, kayak boat, sailing boats, snorkeling and fishing trips. You have access to... View all property information
    Location Information
    Duck Key, Florida Keys
    1 / 30
    5 of 5 stars (36) Excellent
    Key Largo
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Bay front Vacation Condo in Key Largo, Florida. <BR><BR>We book early so don't wait, beat the rest to one of the best and most reasonable, clean, and well appointed condos in beautiful Key Largo, Florida.<BR><BR>We now Accept PayPal, at a small fee.<BR><BR>Beautiful sunsets, water view from our... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 66
    5 of 5 stars (20) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Don't hesitate to call us! Many folks prefer to speak with a real live person. We're here to help :) 517-420-4212 (call or text- anytime!) Read 90+ guest reviews at www.homeaway.com/177656. Welcome to the beautiful Florida Keys! We're Greg and Stevie (Stephanie) Bovee from Carbondale, CO. We... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 13
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** Enjoy spectacular sunsets and beautiful waterfront at **Caribbean Sunset**. This spacious three bedroom, three bathroom home has a well appointed kitchen, three king bedrooms (one converts to two twins) and a beautiful... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 32
    5 of 5 stars (1) Excellent
    Marathon
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Lush Tropical Waterfront Homes with Incredible View, Pool, Tiki Hut and 100' of Deep Water Dockage - Full Duplex (two homes, one property, one price). Spectacular view of the Gulf of Mexico and incredible sunsets. With this full duplex home you get two large side-by-side 2 bedroom, 2 bath homes.... View all property information
    Location Information
    Marathon, Florida Keys 33050
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Central Heating
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    • x
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    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Islamorada
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 19
    5 of 5 stars (1) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    3.5 of 5 stars (3) Average
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    MINI VACATIONS 3 DAYS 2 NIGHTS $250 April 1 - May 15, 2015 This Key Largo property is a paradise in a gated private community. This comfortable park model trailer includes cable TV, full kitchen, bathroom, Queen size bed in master bedroom and much more. Outside terrace with BBQ grill and... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 29
    5 of 5 stars (38) Excellent
    Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 stars (6) Excellent
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
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    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your private deck only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these environmentally... View all property information
    Location Information
    Marathon, Florida Keys 33001
    1 / 17
    5 of 5 stars (19) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Located one hour from Miami, Florida... the Kawama Yacht Club is your escape route to the Florida Keys. Situated at mile marker 100 on the Atlantic Ocean, this gated community offers all you need for a relaxing vacation or getaway. Enjoy the panoramic view this 5th story unit has to offer of the... View all property information
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    Key Largo, Florida Keys 33037
    1 / 31
    5 of 5 stars (23) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • 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 television, 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
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    With a name like Baby Conch you know it is the sweetest most adorable cottage for two that is the perfect size for a romantic get-a-way, anniversary celebration or honeymoon. Step outside the back to a screened porch inviting you further to relax and rejuvenate in your private hot tub. The patio... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 20
    4 of 5 stars (2) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    MINIMUM STAY: 7 NIGHTS. This 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 counters, new cabinetry and appliances. New linens and fresh paint add... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Best Views and most accessible in the Complex!<BR><BR>Large one Bedroom Apartment, overlooking the pool, beach and ocean.<BR><BR>Furnished, with dishwasher, stove, refrigerator, TV and more.<BR><BR>King sized bed in bedroom, full sized sofa sleeper in living room .<BR><BR>Oversized heated pool,... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 7
    5 of 5 stars (3) Excellent
    Key Largo
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    An exceptional vacation spot in beautiful Key Largo. This beautiful condo is on the Florida Bay side of Key Largo at Moon Bay Condos as featured on HGTV, just one mile from John Pennekamp State Park. The condo has just been completely remodeled and redecorated and unlike the other units in the... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 28
    4.5 of 5 stars (2) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This is a spacious, open floor plan, Three bedrooms, Two Bathrooms, 6 people accomodation, brightly painted colors, beautifully furnished. Relax in the upper covered porch or down below to the open and spacious patio leading to the pool. Outdoor Tiki shower hut. The grounds are landscaped with an... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    1 / 5
    4.5 of 5 stars (4) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    Nicely furnished private room and bath in quiet, desirable neighborhood in Old Town Key West. A/C + Cable TV + WiFi. Access to enchanting, large pool/deck area with outside grill. Equipped with microwave and refrigerator. The pool/deck area is beautifully landscaped and available for your use.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located just 90 miles south of Miami and 45 miles from... View all property information
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    Marathon, Florida Keys 33050
    1 / 17
    5 of 5 stars (22) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    About this property
    Forget that "been there, done that" hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and "Sunset Celebration". The original local artwork throughout... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    5 of 5 stars (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Central Heating
    • Outdoor Dining Area
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    • Pet-friendly
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    • x
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    About this property
    .This Exquisitely Furnished Villa With A Breathtaking View of The Gulf of Mexico From the Rooftop Patio is A Dream Vacation Come True! This Beautiful Villa Comes With a Fully Equipped Kitchen. Quality Sheets, Bath Towels, and Bedding. To Get You Started We Include a Sampling of 'Ocean Mist' Bath... View all property information
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    Marathon, Florida Keys 33050
    1 / 44
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located just 90 miles south of Miami and 45 miles from... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 28
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around the area including... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4.5 of 5 stars (4) Very good
    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    "Casa Bella" welcomes you by truly living up to its name. This beautiful bayfrony home in Key Largo, will captivate all your senses with its open water views, lush landscaping, beautiful sunsets, peacefulness, and ever-present marine life. Watch the dolphins swim, swim with manatees by the dock,... View all property information
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    Key Largo, Florida Keys 33037
    1 / 28
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your patio look-out, only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these environmentally... View all property information
    Location Information
    Marathon, Florida Keys 33001
    1 / 21
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (2) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map<BR><BR>Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6<BR><BR>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.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 15
    4.5 of 5 stars (2) Very good
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Enjoy the relaxing, laid back lifestyle of Key Largo. For those who love diving, fishing, snorkling, boating, or just simply letting the world go by while relaxing oceanside. Feel free to contact me whenever you are ready - we are waiting for your call! Beds: 3 King Beds, 1 Sofa Bed View all property information
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    Key Largo, Florida Keys 33037
    1 / 13
    Key Largo
    3 Bedrooms, Sleeps 1 | Quick View
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    Beautiful Location Free Wifi Air Conditioning Additional amenities include: paved parking, pack-n-play, free calls. View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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 'House Boats' are a boat lovers dream with all the comforts of home, including a full... View all property information
    Location Information
    Tavernier, Key Largo 33070
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Child-friendly
    • x
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    • x
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay.<BR><BR>Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 12
    4.5 of 5 stars (8) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    5 of 5 stars (1) Excellent
    Conch Key
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
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    About this property
    If Comfort, Fun, Fishing and Views Are on Your List, Stay Here! We have ground level or second floor units. We provide outside table and chairs, and just around the corner the barbecue grill is located to grill up those freshly caught Florida Keys' lobster or our wonderful assortment of Keys'... View all property information
    Location Information
    Conch Key, Florida Keys 33050