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Holiday Rentals in Florida Keys

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    1 / 27
    5 of 5 bubbles (1) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 bubbles (2) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 18
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 32
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Tavernier, Key Largo 33070
    1 / 23
    5 of 5 bubbles (6) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
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    About this property
    The newly renovated oceanfront condo is located in Tavernier Key, a community situated along the southern border to Key Largo. The grounds encompass over 60 acres and is situated in a tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise waters of the Florida... View all property information
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    Tavernier, Key Largo 33070 3100
    1 / 36
    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located in Key Largo at mile marker 95, oceanside, this pool home will really seal the deal. This home has been remodeled, and offering stunning Atlantic views, the home is ideal for a family seeking a combination of camaraderie and privacy. Divided into separate units on its two floors, each with... View all property information
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    Key Largo, Florida Keys 33036
    1 / 41
    Long Key
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 43
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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 / 55
    Key Largo
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This Studio Apt has a beautiful Kitchen and Bath, tile floors, central zoned Air Conditioning and has views of Florida Bay open bay front. It is located in Kings Kamp RV Park at Mile Market 103.5 Bayside. We have a sandy beach, boat docks, marina, fish cleaning table, free Wi-Fi, 75 channels of... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 31
    5 of 5 bubbles (23) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • Children's Pool
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    • Ocean Views
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    • x
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    • x
    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen televisions, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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    Islamorada, Florida Keys 33070
    1 / 27
    Long Key
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Enjoy a getaway in one of Islamorada's most prestigious neighborhoods when you rent this three-bedroom, three-bathroom home. Located at the end of a cul-de-sac within the Port Antigua neighborhood on Lower Matecumbe Key, the home quickly enchants arriving guests with its peach-colored exterior set... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 35
    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Waterfront
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    • x
    • x
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    • x
    About this property
    Tile floors, Air Conditioning, property on Florida Bay. Sandy beach, boat docks, ramp, marina, fish cleaning table, Wi-Fi, 75 cable TV channels, coin laundry, Ice Machine. Linens provided. Refrigerator, Coffee Maker. Outside patio-sit and watch beautiful Florida Bay Sunsets. 2 night minimum stay.... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 11
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The view, the view and THE VIEW! Ocean breezes to soothe and regenerate your soul. Expansive elevated patios, one screened as a Lanai and one open to the night stars. Just steps away is the immaculate pool and clubhouse where you can enjoy billiards, shuffleboard, tennis and meet friends at the... View all property information
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    Key Largo, Florida Keys 33037
    1 / 16
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    An adorable 2 bedroom and 1.5 bath condo at Summer Seas.  The condo has everything that you need to make sure your stay is very comfortable.  The complex is located right on the bay and has amazing sunsets. Additional amenities include: airbnb rounding adjustment. View all property information
    Location Information
    Tavernier, Key Largo 33036
    1 / 34
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Enjoy this lovely two bedroom two bath garden and pool view unit at 1800 Atlantic, You even get a peep of the ocean from your 40ft private balcony. Located at the Premier 1800 Atlantic complex on the Atlantic ocean at the end of Smathers Beach. This unit has all you need to enjoy and relax with all... View all property information
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    Key West, Florida Keys 33040
    1 / 58
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Overlooking the beautiful tropical courtyard area, This property is totally renovated and tiled throughout. Both bedrooms feature a King size bed for your comfort and a flat screen TV. The unit is colorful and tropical giving you a feel of the Islands. You are just steps away from the fabulous pool... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 42
    Key West
    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
    This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a brand new king size bed. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its new owners. From new interior design work and furnishings courtesy of Royal Furniture of Key West, to new closets and drapes, and local art, including works by Alan Maltz, the vacation tranquility of the... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    4.5 of 5 bubbles (7) Very good
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 42
    3.5 of 5 bubbles (5) Average
    Tavernier
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Porch
    • Terrace
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This is a beautiful home, you will enjoy every minute of your stay here! There aren't many homes built like this in the Keys. The room for rent is the guest room (the other room is occupied), with 14 foot vaulted ceilings, a comfy, queen sized bed and a ladder leading to a crawl space above (see... View all property information
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    Tavernier, Key Largo 33070
    1 / 25
    Key Largo
    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
    Ocean Pointe Suites is a secluded resort overlooking the Atlantic. A great getaway for families or couples. You relax in a gated community located on 67 acres on the Southern tip of Key Largo, in the quiet town of Tavernier. Our property is managed by Tony 954.410.3241 and Ana 954.410.0308. THE... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    1 / 15
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • Hot Tub
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    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 15
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 56
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 39
    Key West
    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
    The Grand Vista - 2 bedroom suite 2 Bedroom 2 bath suite, Totally renovated with flat screen plasma TV's in both bedrooms and the living room. All brand new furniture in Jan 2010, King bed in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in the living room. Full size... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 4
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
    1 / 36
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated bathrooms. Master bathroom has a tub and walk in shower. There is a queen in the master bedroom, two twins in the guest bedroom and a queen sleeper sofa in the living room. Both... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Private Garden
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    • x
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    • x
    About this property
    This Entire Home, a 3 Bedroom/2 Bathroom vacation hideaway will be yours! My place is just a few hundreds yards away from John Pennecamp State Park, one of the most popular tourists destinations in the Florida Keys. It's ideal for a day at the beach and water sports! You’ll love my place because... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 24
    Long Key
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
    About this property
    Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware. All you need to bring is your clothes, bathing suit, fishing gear and... View all property information
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    Long Key, Florida Keys 33001
    1 / 6
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    . This spacious 1400 sq. ft. unit includes 2 Bedrooms, 2 Full Baths, 1 Half Bath. Newly furnished and updated. New 42' flat screen T.V. in l.r. King size bed in Master Bedroom, 2 Twin in Second bedroom. . Wrap around balconies on both levels with spectacular views and colorful sunsets in the... View all property information
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    Marathon, Florida Keys 33050
    1 / 14
    Conch Key
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    The Studio has a King-size bed as well as a pull out futon in the living room. This Villa is literally 10’ from the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee maker, toaster, refrigerator/freezer, stove/oven, dishes, utensils, cookware,... View all property information
    Location Information
    Conch Key, Florida Keys 33050
    1 / 10
    3.5 of 5 bubbles (2) Average
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Keysey home with direct access to the bay or ocean from the dock. Centrally located to stores, restaurants and all that Key Largo has to offer. We are located 2 miles from Pennekamp Park and 4 miles from the Jacobs Aquatic Center. Enjoy the Manatees swimming at the dock or fish and snorkel at the... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 25
    3.5 of 5 bubbles (17) Average
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Tavernier, Key Largo 33070
    1 / 6
    4.5 of 5 bubbles (6) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    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 / 12
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Anyone can rent you their house, I provide a tropical resort with concierge services. This house has it all – a 7 min walk to Sombrero Beach, heated private pool, ocean views, a 'fisherman's' dock, high speed wireless Internet, etc., etc. Marathon recently spent $5M renovating Sombrero Beach -... View all property information
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    Marathon, Florida Keys 33050
    1 / 24
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Ocean view, private beach and marina, free parking, tennis courts, swimming pool 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... View all property information
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    Tavernier, Key Largo 33070
    1 / 36
    Key West
    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
    Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open onto the 40 ft private balcony that has views of the nature preserve and Atlantic ocean. Fully equipped with all the modern conveniences you would need for an enjoyable vacation.... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    2 of 5 bubbles (1) Poor
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This is a Duplex large 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. Full Kitchen with Microwave, Range and Refrigerator. We have Staff on property daily and there is a coin... View all property information
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    Key Largo, Florida Keys 33037
    1 / 19
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tamarind Bay Club is a quiet private gated complex on the beautiful Blackwater Sound in Key Largo, Florida. Located on US Highway 1 between mile marker 104 and 105. It is a 1.5 hour drive from Miami South Beach and 2.5 hours from Key West. Tamarind Bay is conveniently located within walking... View all property information
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    Tavernier, Key Largo 33037
    1 / 24
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. Our condos' at La Brisa are two bedrooms with two full bathrooms on the third floor. The master bedroom has a king size bed with a walk... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (4) Excellent
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76. Near the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    Tavernier
    1 Bedroom, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    In the heart of it all, Plantation Key is the most convenient of all the Keys. We are near a supermarkets, a pharmacy, and a hospital. There are also plenty of restaurants and a movie theater. The neighborhood offers a boat ramp directly on the bay. Ocean access is a short ride through Snake or... View all property information
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    Tavernier, Key Largo 33070
    1 / 24
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • ?
    About this property
    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast.LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33036
    1 / 10
    5 of 5 bubbles (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    <BR><BR>Luxurious direct bayfront townhome with dock, upgraded unit.<BR><BR> best location in the 50's overlooking large green yard and open bay with slip in front.<BR><BR>3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 29
    Long Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
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    Cozy, canalfront, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bedrooms are located in a separated, quiet part of the house, while the living, dining, and kitchen are open for enjoying each... View all property information
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    Long Key, Florida Keys 33036
    1 / 25
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Tavernier, Key Largo 33070