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Florida Keys Island Rentals

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    1 / 43
    5 of 5 bubbles (2) Excellent
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 15
    5 of 5 bubbles (1) Excellent
    Marathon Shores
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 19
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Tucked away on a gated tropical estate, is our 'Island Breeze Cottage'. This cottage is located in the middle of the Estate and steps away from our white sandy beach and those beautiful Gulf of Mexico sunsets !! There is a tiki hut on the beach. And a dock to fish from or go snorkeling right from... View all property information
    Location Information
    Tavernier, Key Largo 33070
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    4.5 of 5 bubbles (2) Very good
    Marathon
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This condo has full resort amenities: Marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables & charcoal grills, security and wifi. Waterfront to the beautiful Gulf of Mexico, parking for boat trailers, with plenty of... View all property information
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    Marathon, Florida Keys 33050
    1 / 17
    5 of 5 bubbles (1) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    No. 1 rated resort in Marathon Completely renovated w/ dock. We will be ready to take reservations for Thanksgiving. 3 bedrooms 1 King, 2 queens and a queen size sleeper. 2.5 bathrooms. Walking distance to Marathon and Key Colony activities. Representing a new concept that offers... View all property information
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    Marathon, Florida Keys 33050
    1 / 43
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 bubbles (3) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    4.5 of 5 bubbles (4) Very good
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 29
    4.5 of 5 bubbles (5) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 14
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 10
    4.5 of 5 bubbles (5) Very good
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This fully furnished 4 Bedroom, 3 1/2 Bath Canal Front Home is the ideal Escape to Paradise. One thing that cannot be seen through photos is the amount of privacy this location has, at the end of the Cul-de-sac with the canal and mangroves surrounding the home. Double Boat Dockage, Large Tiki Hut... View all property information
    Location Information
    Key Largo, Florida Keys 330037
    1 / 26
    Tavernier
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
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    • x
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    About this property
    There is room for the whole family in this 2,200 sq. ft. townhouse with In-Laws quarters. As you enter the first floor you will find an open floor plan with living room, full bathroom and kitchenette with microwave, toaster, coffee maker, portable induction single-burner cooktop, and refrigerator.... View all property information
    Location Information
    Tavernier, Key Largo 33037
    1 / 34
    5 of 5 bubbles (2) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Welcome to Paradise Point, a beautiful private community in sunny Key Largo! In this private and secure gated community of just 32 homes, paradise awaits you! In our home you'll be right on the water with a gorgeous view of a deep-water canal that has easy access to open water. We are located... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 24
    5 of 5 bubbles (2) Excellent
    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Elegant home with many unique, architectural features, located on a family-owned waterfront piece of property, with 3 other rental cottages, sandy beach, and small marina.<BR><BR>This lovely house, "Tropicasa", has everything needed for a large group - full kitchen with granite countertops,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 28
    5 of 5 bubbles (1) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (21) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 bubbles (2) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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 / 22
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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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
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    1 / 12
    5 of 5 bubbles (3) Excellent
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    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 / 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 / 68
    4 of 5 bubbles (9) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Cozy cottage , one bed room studio style with private bathroom and kitchenette.Great location close to local restaurants and bars,2 miles to John Penny Camp State National Park and walking distance to Swim with the Dolphins. .shopping plaza. Bisycles for rent. $10 View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 10
    5 of 5 bubbles (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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 / 32
    4.5 of 5 bubbles (39) Very good
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Downstairs is a... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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
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    Tavernier, Key Largo 33037
    1 / 24
    Key Largo
    6 Bedrooms, 6 Bathrooms, Sleeps 18 | 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
    Key Largo, Florida Keys 33070
    1 / 25
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
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    Islamorada, Florida Keys 33036
    1 / 20
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Completely renovated keys cottage. Classic and charming design with modern amenities. This is a concrete home on the ground level, not a trailer or mobile home. Master suite with bath on ground floor. Two bedrooms upstairs with balcony overlooking Buttonwood Sound. Lots of room for the whole... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 24
    4 of 5 bubbles (4) Very good
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Half duplex located in prestigious Key Colony Beach. Tropical decor throughout. Located on a 100ft. wide canal with quick access to ocean. There is a concrete dock for your boat, and a great patio in the back. You are within walking distance to the "Cabana Club" , a private beach club with a... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33050
    1 / 26
    4 of 5 bubbles (1) Very good
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • x
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    Located in the heart of the national key deer preserve this bright chalet style home with many windows, with very comfortable memory foam mattresses in all the beds, master room has a queen size bed with a 40' flat screen TV, and the guest room is equipped with a very sturdy wood bunk bed with a... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 14
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many... View all property information
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    Islamorada, Florida Keys 33036
    1 / 28
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Beautiful Beachfront Home located directly across the street from famous Sombrero Beach. Sombrero Beach is surely one of the stand-out beaches in the Florida Keys This pet friendly beach has something for everyone. You can swim, lay out, fish, bird watch, BBQ, picnic, watch the sun set, play sand... View all property information
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    Marathon, Florida Keys 33050
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    5 of 5 bubbles (2) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Ocean View Cottages (3) Sea Horse, Horse, Periwinkle 2 bedroom - 2 bath These are ocean view cottages perched in the air 12 feet on pilings open to fabulous views. With a full gourmet kitchen and great attention to detail, this cottage has a warm feel at home ambiance. Kick back and enjoy the... View all property information
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    Marathon, Florida Keys 33050
    1 / 35
    4.5 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Part of the Nightly group unit 4 Flowers 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 / 39
    5 of 5 bubbles (3) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key Largo, Florida Keys 33037
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    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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 / 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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    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
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    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
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    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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    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
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (3) Very good
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful 3-bedroom home on mile marker 90 in the Florida Keys. Our home is located in Tavernier, the Sport Fishing Capital of the World. It is a private, gated home directly on the water with a small pier and... View all property information
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    Tavernier, Key Largo 33070
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    Key Colony Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This spacious and impeccably maintained home sits on a wide, deep-water canal in Key Colony Beach. 2200 sq feet 3 level home! Free Access to a pool and ocean front beach at a private club within walking distance. Lower Level has 1 bedroom, 1 bathroom living area and small fridge. Main Level has... View all property information
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    Key Colony Beach, Florida Keys 33051
    1 / 34
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 bubbles (42) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
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    Key West, Florida Keys 33040
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    Marathon
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    Marathon, Florida Keys 33050
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    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to our newly renovated, little slice of paradise on mile marker 105! Come and relax at our beautiful Key Largo home, located in the Sport Fishing Capital of the World. Just minutes from John Pennekamp Park and the world famous Tiki Bar as well as many dining, shopping and grocery options.... View all property information
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    Key Largo, Florida Keys 33037
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    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    In one of the most desirable locations in Key West, you will find the exquisite 2CoolFish. Located in Truman Annex. Just walking into this pristine home will take your breath away. Featuring two bedrooms and one and a half bathrooms, this home is perfect for a family or small group of friends... View all property information
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    Key West, Florida Keys 33040
    1 / 40
    5 of 5 bubbles (10) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 Fabulous 3 bedroom PREMIUM UPGRADED Town Homes with 31 ft dock slip in Marathon Florida`s Finest Resort... View all property information
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    Marathon, Florida Keys 33050
    1 / 30
    Key Colony Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Garden
    • Secure Parking
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    • x
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    About this property
    This adorable, well-lit 3 bedroom, 2 bath duplex is on a canal, features a fishing table and is perfect for family reunions, weddings or vacation rentals of any kind. The Florida Keys are internationally known for their natural beauty, spectacular weather, world class fishing, snorkeling and... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051