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Vacation Rentals in Islamorada, FL

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    Travellers to Islamorada are booking February dates now. Secure your vacation rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that... View all property information
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    Islamorada, Florida Keys 33070
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Sip a margarita under your indoor 'tiki hut' or from your bamboo bar in the living room. Located in the heart of the Florida Keys, adjacent to Founder's Park, less than one hour from Miami and 87 miles from Key West, let Executive Bay be your secluded getaway. Must rent 29 Days or more!... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This canal front, custom built home with access to a private beach, has 4 bedrooms & 3 full baths. The house has custom wood work throughout. Cypress tongue and groove ceilings with cedar beams, the kitchen has an exotic Honduras mahogany countertop , Jenn air range & wine cooler. All the... View all property information
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    Islamorada, Florida Keys 33036
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    3 of 5 bubbles (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Gorgeous home in the premier gated community in Islamorada. Bonefish Bay, an enclave of 12 Key West-style homes with all the amenities of a large resort. White sand beach, tennis court, boat ramp & dockage with beautifully manicured grounds. Family oriented and extremely kid-friendly. Each home... View all property information
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    Islamorada, Florida Keys
    1 / 25
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful, newly renovated town home 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 tennis... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautiful home with 3 bedrooms and 2 bathrooms,everything renovated,kitchen remodeled with stainless steels appliances ,the house have comforted beds for 10 people's ,backyard area with BBQ ,private parking inside the house for 6 cars,private ramp for boat and jetski inside the house,beautiful... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 25
    5 of 5 bubbles (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    *** Owner is highly motivated to rent! Contact us for discounts *** Beautiful three bedroom bayside townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful town-home in the Florida Keys. The Executive Bay... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
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    Mina Bay - vacation rental with "the million dollar view"! Truly OCEANFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly... View all property information
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    Islamorada, Florida Keys 33036
    1 / 11
    4.5 of 5 bubbles (5) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    *** Owner is highly motivated to rent! Contact us for discounts *** Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated town home in the Florida... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    *** Owner is highly motivated to rent! Contact us for discounts *** Beautiful two bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to your home away from home! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful town-home in the Florida Keys. The Executive Bay... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    BEAUTIFUL BAYFRONT HOME WITH SUNSETS FROM EVERY ROOM BRAND NEW FURNITURE! 6 Month + 1 day Rental Fish the backcountry or the Ocean, just minutes away. House has 3 bedroom suites with king beds in every room. Deep water dockage, capable of handling large boats. 100' dock. Very private... View all property information
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    Islamorada, Florida Keys
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Corner lot, Clear and deep waterways, 3 bedrms, 3 bath, sleeps 8+ Granit Tops This home is located in a prime neighborhood with 150lf of seawall for all your water toys. 3 bedrooms, 3 full bath ,1 king, 2 queens and bunkbeds, Laundry room, Wet bar, Library/Sitting room, Living /Family room and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    5 of 5 bubbles (1) Excellent
    2 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 *** Welcome to our newly renovated, little slice of paradise! 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    Come to Paradise and Enjoy it with Comfort, and Style! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Highend remodeled and luxuriously furnished bay view condo in the gated community of Futura Yacht Club. 2 bedroom 2 full bath Condo with a open den that can be closed off as a third room (queen size murphy bed). Flat screen tv in every room with cable and wifi. Gorgeous modern kitchen with eat in... View all property information
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    Islamorada, Florida Keys 33070
    1 / 26
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Balmy weather, sunshine and a little magic await you in the Florida Keys… Look no further than this exquisite Islamorada vacation rental home as your own personal oasis during your upcoming tropical getaway! Nestled in the exclusive oceanfront gated community of Angler’s Reef in Islamorada on... View all property information
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    Islamorada, Florida Keys 33036
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Keys Kottage Villa is located in beautiful Islamorada, Florida Keys. We are on mile marker 82. Private Marina access and trailer parking available to guests. Bring your boat and or pet. We can accommodate up to 26 ft. vessels. This is a Fisherman's dream for a week of fishing. Please call for... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on... View all property information
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    Islamorada, Florida Keys 33036
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a... View all property information
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    Islamorada, Florida Keys 33070
    1 / 16
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Beautiful professionally decorated condo in Futura Yacht Club. Pool, club house, Tennis, Marina with great fishing. Marker 88 restaurant is a short paddle board away. Private beach with sun set view. Perfect location near everything, restaurants, bars, shopping. Diving centers ,fishing, boat... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    *** Owner is highly motivated to rent! Currently we have January 2017 on Promotion. Contact us for discounts *** Infinite ocean views, breezy sunsets and the soothing sound of swaying palms is the tip of the iceberg at this spacious, modern and luxurious oceanfront condo in the Keys. SLEEPING... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** This water front home is located oceanside in the tropical Lower Matecumbe key, Islamorada, mile marker 73 (The Sport Fishing Capital of the World). It features a 15' wood dock and 12’ wide ramp, so you can bring your own boat and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 31
    5 of 5 bubbles (12) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and... View all property information
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    Islamorada, Florida Keys 33070
    1 / 30
    5 of 5 bubbles (7) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • x
    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new... View all property information
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    Islamorada, Florida Keys 33036
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Premier condo in Islamorada in Upper Florida Keys. Located on 12-acre property with 1,100 feet of oceanfront. Gated complex, large swimming pool, sand beach, and two tennis courts as well as boat ramp and dedicated slip. Spectacular Atlantic Ocean views. This top-floor, freshly-remodeled 2 bed 2... View all property information
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    Islamorada, Florida Keys 33036
    1 / 20
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Beautiful three story luxury home in the heart of Islamorada the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 8
    4.5 of 5 bubbles (5) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Weekend Getaway!!! Enjoy the most beautiful sunsets on earth from this gorgeous 4 bedroom, 5 bathroom plus casita, tropical paradise. There are two master suites, one entry level (no stairs) and one on third floor, both with amazing views. Comes complete with Bayfront pool and lounge area that will... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    5 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and ceiling fans... View all property information
    Location Information
    Islamorada, Florida Keys 33070
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