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Holiday Rentals in Florida Keys, FL

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    1 / 21
    5 of 5 bubbles (25) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 30
    4 of 5 bubbles (1) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 25
    5 of 5 bubbles (4) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 43
    5 of 5 bubbles (2) Excellent
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Mariner's Club 606 in Key Largo is one of a kind with it's resorts style pools and amenities that will meet the expectations of anyone looking for a high end, high quality place to stay and truly enjoy this beautiful part of the world! It is a private community tucked away in between palm trees,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 6
    4.5 of 5 bubbles (6) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving.... View all property information
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    Key Largo, Florida Keys 33037
    1 / 34
    Big Pine Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful home very centrally located in the heart of Big Pine key this 3 bedroom 2 bathroom home is close to everything that lower keys has to offer, Bahia Honda State Park which has one of the most beautiful beaches in the country is only 3.5 miles away as well as 29 miles away from Key West and... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 31
    4.5 of 5 bubbles (12) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4 of 5 bubbles (1) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard and Banana's Foster Guesthouse and across the street from Seaport Suite. The location itself could not be better!... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 bubbles (23) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Abaco Suite, is a bi-level suite with a very spacious... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Patio
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    • x
    About this property
    Plan your next Shore Leave at this gorgeous waterfront Key Largo home on Largo Sound, Oceanside near Mile Marker 103! Beautifully furnished and updated, with living room, kitchen and half-bath at ground level & 3 bedrooms & 2 bathrooms upstairs. Master bedroom has a Queen bed. Guest bedroom #1 has... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 29
    4.5 of 5 bubbles (32) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • x
    About this property
    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    5 of 5 bubbles (7) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 29
    4.5 of 5 bubbles (2) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 bubbles (49) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Located in the Kawama Yacht Club with full access to a boat ramp, our unit sleeps 8 guests comfortably. A queen size aero bed and a pack and play are also available. The unit is equipped with central air conditioning, dishwasher, washer/dryer, new TVs, high-speed WiFi access, and it's well-stocked... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 45
    Key Largo
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Stay at a Luxury Townhome. Recently remodeled... Everything is new! Beautiful kitchen fully equipped , TV in each room, three patios, located just off the heated pool (literally 20 steps away from the pool) plus a kiddy, parking is right outside the front door. Beautiful sunsets from the balcony... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 30
    4.5 of 5 bubbles (8) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    • ?
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    • x
    About this property
    Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
    Location Information
    Key West, Florida Keys
    1 / 35
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 38
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully equipped eat in Kitchen, Washer/Dryer. Expansive private balcony overlooking the lush... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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    • x
    About this property
    Beautifully Remodeled Home w/Neighborhood Dockage and Board Ramp. This charming home is surrounded by mature trees making it very private, beautifully updated, offering 2 bedrooms 1.5 bathrooms (split floor plan), awesome screened in porch, car port, tons of storage, large kitchen pantry, balcony... View all property information
    Location Information
    Tavernier, Key Largo 33070
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    1 / 29
    4.5 of 5 bubbles (28) Very good
    Key West
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (2) Excellent
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Part of Southernmost Sanctuary Suites The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    4 of 5 bubbles (7) Very good
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    Listen to the tropical songbirds at sunrise. Walk to John Pennekamp Park. Get away from the hustle and bustle of South Florida. This property is nicely landscaped with palms and flowers and has a water view. There is a neighborhood park 100 meters away with water access for kayaking , swimming,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 14
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Grill
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    • Pet-friendly
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    • x
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    • 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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 69
    4.5 of 5 bubbles (16) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Clean one bedroom and one bathroom cottage. Full size kitchen ,dinning room, sleeping couch on family room. Cable and internet are included., great location walking distance to swim with the dolphins .and 2 mile to the world famous John penny Camp State National Park. close to restaurants and... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 22
    5 of 5 bubbles (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    About this property
    This house has everything! You can rent 1/2 or the whole house. The top unit has 2bd/ 2bths. Lower spacious unit has 1bd/1bth. Enjoy dinner on breezy upper or lower outdoor patios. This house is more convenient and offers much more than your ordinary 3/3. Each unit is very spacious, sleeps up to... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 24
    4.5 of 5 bubbles (31) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    About this property
    The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 bubbles (14) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    4 of 5 bubbles (2) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • x
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    About this property
    Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    Key West
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    In the heart of tropical key largo, Port Largo Villas has an atmosphere of a 5 star resort with its own sandy beach and within walking distance to Marina Del Mar (305.451.4107 call Dock Master to reserve slip). For the water enthusiasts, it doesn't get any better for sportfishing, diving,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 29
    3.5 of 5 bubbles (2) Average
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Paradise point! This is a newly renovated (Spring 2014) home in a private gated community. Located at mile marker 106 on the bayside in Key Largo, this home is an ideal location for those looking to enjoy life on the water in the Florida keys. The home is situated for convenient access to... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 10
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a two-story typical keys-style home, w/ two bedrooms & two baths. One bathroom is on the ground floor, serving the two bedrooms, & the other is near the living/dining area upstairs. A large sun deck located in front overlooks the marina across the street, & a short walk down the block is... View all property information
    Location Information
    Tavernier, Key Largo 33037
    1 / 27
    4.5 of 5 bubbles (32) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors. Key West Vacation Rentals... View all property information
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    Key West, Florida Keys 33040
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    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    • Balcony
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    • x
    About this property
    Located just steps from Duval St - right off the corner of Amelia and Duval - "Duval Quarters" is the perfect combination of location, luxury and roominess! This 1 bed 1 bath condo is a part of the historic Casa De Luces condominium complex and is now managed by Key West Vacation Rentals, which... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
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    • ?
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    • x
    About this property
    (Recently updated!) Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    4.5 of 5 bubbles (2) Very good
    Marathon
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    Comfortable studio condo with full kitchen and a full size pull-out couch for extra guests. This condo has full resort amenities from a marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables and charcoal grill, along... View all property information
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    Marathon, Florida Keys 33050
    1 / 33
    4.5 of 5 bubbles (24) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
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    • x
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    Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
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    Key West, Florida Keys 33040
    1 / 7
    5 of 5 bubbles (5) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This totally updated condo features full ocean views from almost every room. Watch the sun rise from the balcony as you enjoy your morning coffee. Enjoy an evening cocktail out on the jetty. Take it easy by the pool or enjoy the water sports and fine local seafood restaurants in the area. The... View all property information
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    Tavernier, Key Largo 33037
    1 / 27
    4.5 of 5 bubbles (8) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 bubbles (27) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    Hibiscus Hideaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St. Welcome to the perfectly located and affordable apt Hibiscus Hideaway. You will not find a better spot to spend your sunny days and exciting... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    Marathon Shores
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    Beautifully decorated, extra clean, new furniture, fully equipped kitchen brand new hot tub, along with everything you will need to make your stay comfortable. Walking distance to one of the most beautiful beaches in the Florida Keys. Only minutes away from the 7 mile bridge where you could walk... View all property information
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    Marathon Shores, Marathon 33050
    1 / 27
    4.5 of 5 bubbles (21) Very good
    Key West
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute walk away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    Key Colony Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This spacious and impeccably maintained home sits on a wide, deep-water canal in Key Colony Beach. 2200 sq feet 3 level home! Free Access to a pool and ocean front beach at a private club within walking distance. Lower Level has 1 bedroom, 1 bathroom living area and small fridge. Main Level has... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 15
    4 of 5 bubbles (5) Very good
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Sauna
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    • x
    • x
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    • x
    About this property
    VILLAGE OF ISLAMORADA REQUIRES MINIMUM OF 29 NIGHT STAY Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 40
    4.5 of 5 bubbles (24) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Quaint cottage located on mile marker 100. Key Largo is known as the 'Dive Capital of the World.' John Pennekamp Coral Reef State Park has two beaches, and a replica of a shipwreck in the water which is great for snorkeling. We are located only a few blocks from the Marina where you can go fishing,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 7
    5 of 5 bubbles (3) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
    About this property
    Minimum rental is 30 days. Our 2/2 modern comfortable house has plenty of dock space (over 100 ft.) and is very close to our community boat ramp. Do you like back-country (shallow water and remote) or deep sea fishing, scuba diving or snorkeling, sailing, nature-watching, canoeing or just... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 32
    4.5 of 5 bubbles (39) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Downstairs is a... View all property information
    Location Information
    Key West, Florida Keys 33040