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Vacation Rentals in Florida Keys, FL

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    1 / 21
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 27
    Key Colony Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 16
    5 of 5 bubbles (1) Excellent
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 33
    4.5 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 32
    4.5 of 5 bubbles (29) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details.... 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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    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 / 22
    5 of 5 bubbles (1) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. Very Clean 2 bedrooms, 2 bath home with over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap around walkway.... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 16
    4.5 of 5 bubbles (3) Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    About this property
    Ocean Pointe Suite is located directly on the Atlantic Ocean. This unit is renovated and is located in building 1. Featuring beautiful views from the living room, kitchen and porch. This unit offers 1 King bed in master bedroom, 1 Queen bed in guest bedroom, a pull out queen sofa, 400 thread count... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 9
    5 of 5 bubbles (5) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This spacious 2/2 has a giant deck for lounging with pool, shuffleboard and horse shoes on property. Boat slips available and just 10 minutes by boat to the reef. Walk to Sharkeys pub for some awesome food. Dive and Charter boats are just 5 minutes away on foot! This is THE place to stay in Key... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 25
    4.5 of 5 bubbles (14) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork sandwiches and homemade ice-cream at the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (3) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    4.5 of 5 bubbles (16) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located at Papa's Hideaway, the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
    Location Information
    Key West, Florida Keys
    1 / 39
    5 of 5 bubbles (3) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This condo is located on Mile 104 on one of the best areas of the Keys and just few miles of Pennekan Park and Harris Park. The Apartment has been redecorated and on floor 4 with spectacular views of the bay and stunning sunset. View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 22
    5 of 5 bubbles (2) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    4.5 of 5 bubbles (11) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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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 / 52
    5 of 5 bubbles (14) Excellent
    Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    5 of 5 bubbles (3) Excellent
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
    Location Information
    Key West, Florida Keys 33040
    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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    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 / 28
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 21
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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
    1 / 23
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4 of 5 bubbles (2) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Resort in Key Largo 'located in the town of Tavernier' at the southern edge of Key Largo island, along the designated scenic drive on US Hwy 1. This is a perfect location for those who love to get out onto the water, or to observe the local wildlife. The tropical birds in this area are amazing.... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    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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    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
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    Key West, Florida Keys
    1 / 27
    4.5 of 5 bubbles (8) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 / 13
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
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    About this property
    THE MOON BAY PENTHOUSE located beautiful Key Largo. This beautiful Penthouse condo is on the Florida Bay side of Key Largo at Moon Bay Condos just one mile from John Pennekamp State Park. The Penthouse condo is 1 of 2 original, top floor, large Penthouse units that includes 2 parking garages that... View all property information
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    Key Largo, Florida Keys 33037
    1 / 24
    5 of 5 bubbles (14) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    If you want peace and quiet and disconnect from the daily stresses of life, this is the place to be! Come enjoy all that the Florida Keys has to offer in this 'home away from home' Your reservation includes so many amenities! Great for a well-deserved get-away or Mini-vacation! Located in the... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 39
    4.5 of 5 bubbles (10) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
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    Key West, Florida Keys
    1 / 26
    4 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (4) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    5 of 5 bubbles (9) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of concrete seawall with bumpers... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 10
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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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 / 33
    4.5 of 5 bubbles (24) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 34
    4.5 of 5 bubbles (2) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropical setting. The living... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (3) Very good
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4 of 5 bubbles (1) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(shared... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    4 of 5 bubbles (3) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key Largo, Florida Keys 33070
    1 / 17
    4 of 5 bubbles (8) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area.... View all property information
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    Marathon, Florida Keys 33050
    1 / 27
    4.5 of 5 bubbles (21) Very good
    Key West
    2 Bedrooms, 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 / 22
    4.5 of 5 bubbles (13) Very good
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee... View all property information
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    Islamorada, Florida Keys 33037
    1 / 25
    5 of 5 bubbles (4) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 bubbles (49) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 / 30
    4.5 of 5 bubbles (3) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off by... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    5 of 5 bubbles (3) Excellent
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • 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 / 27
    4 of 5 bubbles (4) Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people in your party, or big family, or want to have some privacy from your friends or... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 25
    4.5 of 5 bubbles (13) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • x
    About this property
    Cozy Condo in Prime Location! Right off of Duval Street! Located just steps off of world famous Duval Street, Duval Canopy is the perfect blend of comfort, location and value. Just a few blocks from The Southernmost Beach, the Southernmost Point, and other favorites like The Butterfly Conservatory... View all property information
    Location Information
    Key West, Florida Keys 33040