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Holiday Rentals in Florida Keys

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    Travellers to Florida Keys are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 23
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    4 of 5 bubbles (4) Very good
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 24
    5 of 5 bubbles (1) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 15
    4 of 5 bubbles (5) Very good
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
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    Tavernier, Key Largo 33070
    1 / 11
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Location, Location, Location!! Sunrise off Southard is a cozy one bedroom condo located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St.... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This is a Duplex 1 bedroom apartment located in Kings Kamp RV Park which has a Marina, Docks, Beach and magnificent sunsets. Tile Floors, air conditioned, cleaned, freshly painted. We have Staff on property daily and there is a coin laundromat for your convenience. Located across the street from... View all property information
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    Key Largo, Florida Keys 33037
    1 / 27
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    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
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    Key West, Florida Keys 33040
    1 / 34
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    5 of 5 bubbles (2) Excellent
    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Tropical paradise in Historical Tavernier, Florida, perfect for your family vacation! Conveniently located Oceanside at Mile marker 92.5, one hour drive from Miami. Easy ocean access and Tavernier Creek cuts through to the bayside just minutes south of our channel. Open plan living area is bright... View all property information
    Location Information
    Tavernier, Key Largo 33070
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    1 / 30
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (37) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    Marathon
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to paradise! Dolphin Bay in Marathon is close to all the Keys has to offer and more! It is located at the friendly Gulf Pointe II complex. We have great views, breezes and impeccably kept grounds. There are only 20 units, so our place is quiet, uncrowded and relaxing. There are great... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 23
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer! When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees... View all property information
    Location Information
    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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    • ?
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    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 9
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
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    About this property
    The FL Keys is Monroe County. B&B's and the like are not legal here (to rent less than 28 days) so we don't. We let our guest, (individuals and couples) stay up to 2 nights free, with the purchase of a one hour $250 boat tour. It is a certain win / win. One should always get on the water when... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 32
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Due to licensing restrictions, this property has a minimum stay of 28 nights. Aqua Pearl Crest is a recently and completely remodeled 3 bed 3.5 bath home with a private pool, off-street parking & an outdoor shower. The open-concept kitchen is outfitted with stainless steel appliances and granite... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (16) Very good
    Marathon
    3 Bedrooms, Sleeps 6 | Quick View
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    • Washer
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    • x
    About this property
    PRICES ARE BEFORE FEES Florida Keys Vacation Rental 7 night minimum Pricing and availability subject to change, please contact Coco Plum Vacation Rentals for updated calendars and prices Indigo Reef #3 ~ Seaside Escape by Coco Plum Vacation Rentals INDIGO REEF FLORIDA KEYS VACATION RENTAL HOME #3... View all property information
    Location Information
    Marathon, Florida Keys 33050
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    1 / 18
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    2 of 5 bubbles (1) Poor
    Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    ***There will be maintenance scheduled in the apartment underneath this rental starting in November 2016 and lasting throughout approximately through March 2017. Moderate noise can be expected Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Take a dip in our gorgeous new pool, or jacuzzi (for 14 people)! Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. The suite offers a... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 26
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Look no further you have found a beautiful 2 bedroom 2 bath "Shot-Gun" house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect "get away" spot for individuals looking to fully immerse themselves in Key West culture. This house is located in on Royal St. in Old Town Key West. It is located only a few blocks from Duval St and... View all property information
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    Key West, Florida Keys 33040
    1 / 5
    Islamorada
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    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
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    Islamorada, Florida Keys 33036
    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
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    Key Largo, Florida Keys 33037
    1 / 45
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    This is an Efficiency 1 bedroom apartment located in Captain Jax's RV Park which has a Marina, Docks, Beach and magnificent sunsets. Tile Floors, air conditioned, clean. Cook top, Microwave-Refrigerator. Full Kitchen, Water View. Park outside your door. Laundromat on premises. Couch can... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 37
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    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
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 7
    4.5 of 5 bubbles (9) Very good
    Key Largo
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    SPECIAL SEPT. OCT. AND NOV RATES This renovated 4 bedroom 2 bath house is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Minutes from best fishing and diving in the world. Come to the... View all property information
    Location Information
    Key Largo, Florida Keys 33170
    1 / 18
    Tavernier
    2 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
    Take a dip in our gorgeous new pool, or jacuzzi (for 14 people)! Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private gatehouse and road. The suite offers a... View all property information
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    Tavernier, Key Largo 33070
    1 / 20
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Resort in Key Largo, located in the town of Tavernier, Florida, is at the southern tip of Key Largo island Enjoy a resort in southern Florida's subtropical zone, with easy water access, a hotel bar and restaurant, and fun Florida Keys town nearby. This location is keen for those who like to get out... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    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 / 11
    4 of 5 bubbles (1) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    • x
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    About this property
    Updated and comfortable 2 bedroom, 1 and 1/2 bath condominium in Moon Bay Resort in beautiful Key Largo, Florida. Pool, tennis court, marina with boat slips and clubhouse are just some off the amenities. This property has a screened patio and covered parking space . Condo is fully equipped with... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 14
    Summerland Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Stunning Atlantic Ocean views from dining area, living room and both bedrooms. Sunrise on the left, sunset on the right and in between 180 degrees of open ocean. Our vacation home is located in exclusive Summerland Key (mile marker 24.5). Whether you are daring adventurer or a more indoor type of... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    1 / 5
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
    • Hot Tub
    • Washer
    • Satellite TV
    • Waterfront
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our Tavernier family vacation home is like 'home away from home'. Property is fenced. Nicely decorated and tiled throughout our home is very well kept and clean only four homes from open Bay access with clear water canal and direct ocean access via Tavernier Creek. Master bedroom features queen... View all property information
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    Tavernier, Key Largo 33070
    1 / 53
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Private Outdoor...
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    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    Marathon
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ocean Front - Villa Bali inspired Florida Keys beauty on Privately owned Walker's Island. This is a spacious 5 bedroom, 5.5 bath home with luxury in every detail and design. Features include cathedral ceilings, marble, stainless steel and and mahogany finishes, and fireplaces in the living room... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 12
    4.5 of 5 bubbles (7) 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
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 43
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
    • Sauna
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    • Private Outdoor...
    • Grill
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you would need. Both bedrooms and the living room have sliding glass doors that open onto an extensive private balcony with the best view in Key West. You can lie in bed and watch the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    5 of 5 bubbles (1) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • DVD Player
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 38
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
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    Key West, Florida Keys 33040
    1 / 105
    4 of 5 bubbles (2) Very good
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
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    • Ocean Views
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Modern, clean, and cozy 2 beds/1 bath bunk house accommodating up to 6 guests located on a full amenity resort and marina with provided towels and linens. Unit includes a full kitchen set up with provided kitchenware, coffee pot, toaster, dishes, and utensils. Equipped with TV, cable TV, one double... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 29
    5 of 5 bubbles (1) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full vanity, and an open, spacious living room with beautiful furnishings.... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the... View all property information
    Location Information
    Tavernier, Key Largo 33036
    1 / 6
    3.5 of 5 bubbles (5) Average
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Porch
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 15
    5 of 5 bubbles (3) Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 26
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. The recently remodeled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the pool. The veranda provides an excellent place to sit, relax & enjoy the... View all property information
    Location Information
    Key West, Florida Keys 33040