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Holiday Rentals in Florida Keys, FL

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    1 / 33
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Marathon
    7 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    1 / 44
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    4.5 of 5 stars (19) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4 of 5 stars (1) Very good
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    For your next escape to the Florida Keys, reserve a stay at this delightful waterfront Cudjoe Key vacation rental home. Perfectly situated on a canal with easy access to the area’s most notable attractions, this serene house has everything you need for a relaxing island retreat! Featuring 2... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33462
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Key Colony Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    2600 SQ FT WATERFRONT HOME POOL HEAT. WAKE UP IN YOUR OWN SUNRISE PARADISE. HAVE COFFEE WHILE SITTING UNDER YOUR GAZEBO BY THE POOL. THIS CUSTOM BUILT, FULLY AIR CONDITIONED, VACATION HOME HAS ALL THE AMENITIES TO MAKE THIS THE MOST MEMORABLE VACATION YOU WILL EVER EXPERIENCE. VERY STYLISH,... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33050
    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
    Marathon Shores
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Enjoy a private island paradise located at MM50. East Sister Rock Island is 1/4 of a mile off the Atlantic Shores off the City of Marathon in the Florida Keys. On the private island sits a dream come true getaway home with 5000 sq.ft of living area which includes a 2700 sq.ft. covered veranda,... View all property information
    Location Information
    Marathon Shores, Marathon 33050
    1 / 14
    4.5 of 5 stars (3) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 31
    Tavernier
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    Sweet little home away from home. This 1 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 3rd floor balcony. If you are looking to get out on the water the complex... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 20
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Luxury condominium in Key Colony Beach with the best panoramic ocean views! Nice furnishings, well equipped modern kitchen with stainless appliances. Washer, dryer, dishwasher, microwave, gas grill. Second story unit with 2 bedrooms, 2 baths. Both bedrooms have queen beds. Beautiful water views... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 34
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 23
    5 of 5 stars (1) Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    <b> Minimum Rental: 1 Month </b> Location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 17
    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    The Great Islamorada Getaway features a spectacular canal front home on an over-sized property with 136 feet of dock space and an in ground pool (heater/chiller optional). Large outside patio with gas grill and upstairs screened in porch. Brand new kitchen and appliances enhance the spacious open... View all property information
    Location Information
    Tavernier, Key Largo 33070
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    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
    Marathon
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    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
    Location Information
    Marathon, Florida Keys 33050
    1 / 6
    4 of 5 stars (4) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Porch
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    • x
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    About this property
    2 bedroom, 1 bath waterfront condo with a Center console boat at your front door. The unit is located in a small complex within walking distance to restaurants, bars and Park. Comes with Flat screen tv's, wifi, dvd player, washer and dryer. Barbecue on patio. Boat is equipped with VHF, GPS and... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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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
    Location Information
    Tavernier, Key Largo 33070
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    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 / 22
    4 of 5 stars (1) Very good
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 51
    5 of 5 stars (8) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it... View all property information
    Location Information
    Marathon, Florida Keys 33156
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to a haven in the Florida Keys! Indigo Reef is located in Marathon, in the heart of the Florida Keys only 90 miles south of Miami. Experience an incomparable Keys vacation in one of the unique waterfront Villas. The luxury bay view villas exude a private vacation paradise, where guests will... View all property information
    Location Information
    Marathon, Florida Keys 33050
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 31
    Marathon
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    **PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN** **Dolphin Bay** is a lush tropical setting offering both quiet and privacy. This spacious four bedroom home is located directly on the Gulf of Mexico. Watch the dolphins, sunsets, or just enjoy beautiful gulf views from... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 11
    4.5 of 5 stars (3) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    About this property
    Beautiful Keys luxurious home at canal five house from Atlantic Ocean . It offers 50ft dock along with powers . Through boat about 4/5 minutes to Vaca Cut & about 7/9minutes distance from 7 miles Bridge . About 20 minutes distance from the Sombrero Reef . Through land about 10 minutes short... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 13
    Tavernier
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    28 NIGHT MINIMUM RENTAL - NO EXCEPTIONS. (I don't respond to inquires of less than 28 nights.) SEPTEMBER or OCTOBER $3500!!! A beautiful, relaxing 5 bedroom home at Harry Harris Beach (mile marker 92.5). Enjoy the heated in-ground pool and attached spa in the enclosed back yard.... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 27
    5 of 5 stars (1) Excellent
    Marathon Shores
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This sweet manufactured home is located in a small, very quiet mobile home community in the heart of the Florida Keys~ Marathon. One bedroom with brand new Queen bed, armoire, and dresser with 40" flat screen t.v. mounted on the wall.....bath with tub/shower combination. Fully equipped... View all property information
    Location Information
    Marathon Shores, Marathon 33050
    1 / 12
    4.5 of 5 stars (9) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    About this property
    Newly remodeled 1,200 + square footage home in the Bayhaven Community. This house has a master bedroom very tastefully decorated as well as a second bedroom with full/twin bunk bed, and a queen sleeper sofa in the living room. Open layout allows you to cook, eat and relax while spending quality... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 25
    5 of 5 stars (43) Excellent
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging... View all property information
    Location Information
    Key West, Florida Keys
    1 / 20
    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    KEY WEST only a 25 minutes drive. Bahia Honda (Beach) National Park 10 minutes...local - Looe Key National Marine Santuary for the Best Diving/Snorkling - 5 mile of reef Near Content Key Reef (Gulf side) - Best Lobstering! Depth 8-15' Good for Novice to experienced snorklers and divers. VERY... View all property information
    Location Information
    Ramrod Key, Florida Keys 33042
    1 / 21
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Here is your key to an unforgettable vacation on the ocean and on the beach. This 3 bedroom, 3 bath house has everything you need for a memorable stay, It is located in a gated community approximately 150 feet from the ocean. We are near Vaca Cut between Grassy Key and Vaca Key for easy access... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 21
    5 of 5 stars (5) Excellent
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (7) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    About this property
    7 day minimum please Key West Vacation Rental This fully furnished newly updated getaway! It is so close to all the Beach, our pool and the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    Sunrise Suites Resort is an island paradise. Complimentary 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (1) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    Islamorada
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    This newly remodeled & renovated (in 2012), two bedroom, Sea Gulls Condo unit, located on the ocean side of Plantation Key at Mile Marker 90, has an awesome view! Unit is comfortably and stylishly furnished, has TVs in the living room, two queen beds and a sleeper sofa. Sea Gulls has a nice pool,... View all property information
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    Islamorada, Florida Keys 33070
    1 / 33
    5 of 5 stars (1) Excellent
    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • x
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    • x
    About this property
    MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious and surrounded by tropical... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 25
    4.5 of 5 stars (13) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
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    • x
    • x
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    • x
    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a "cozy condo hideaway in the heart of historic Key West." The historic significance is close to home. It starts with the white stucco building that houses this suite and other... View all property information
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    Key West, Florida Keys
    1 / 28
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make your self at home in our home away from... View all property information
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    Islamorada, Florida Keys 33070
    1 / 32
    3.5 of 5 stars (3) Average
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Part of TROPICAL VILLAGE Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the... View all property information
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    Key West, Florida Keys 33040
    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
    Location Information
    Marathon, Florida Keys 33050
    1 / 19
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building.  Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    5 of 5 stars (2) Excellent
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    <b> Minimum Rental: 1 Month </b> Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates a boat up to 30' (33' from bow to... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 17
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Sauna
    • Waterfront
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    • x
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    • x
    About this property
    LOCATION, LOCATION, LOCATION LOCATION: Key Largo Florida, the perfect island with easy access to mainland Florida. LOCATION: Moon Bay is centrally located in Key Largo with easy access to all of the great dining, Tiki bars, fishing, diving, kayaking and all the other awesome things the... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 12
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Hot Tub
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    • x
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    • x
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    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key Colony Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
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    This 2100 sq ft bright and spacious property is located just 3 houses back from the canal entrance to Shelter Bay, which provides quick access to the Ocean or Gulf. It also includes membership to the Cabana Club, which is oceanfront with a beach, heated pool, activities restaurant and bar. Key... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 78
    4.5 of 5 stars (63) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Rated Flip Key Top Rental two years in a row 2012 and 2013. Rated "Excellent" by Flip Key and Trip Advisor Guests! You will truly enjoy this Key Largo vacation home! It is conveniently located at mile marker 103.5 adjacent to world famous John Pennekamp Coral Reef State Park, where you can... View all property information
    Location Information
    Key Largo, Florida Keys 33037