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Holiday Rentals and Homes in Islamorada, FL

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    Travellers to Islamorada are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    MINIMUM STAY 29 DAYS. -JANUARY SPECIAL - JANUARY SPECIAL - LET'S MAKE A DEAL - CONTACT US TODAY! BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the... View all property information
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    Islamorada, Florida Keys 33070
    1 / 27
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    MINIMUM STAY: 29 DAYS FISHERMANS PARADISE is this pleasing well maintained waterfront stilt home. It is conveniently located in Tavernier with easy access to the most popular restaurants, shopping and attractions in the upper Keys. The deep and wide canal makes it easy to turn your boat... View all property information
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    Islamorada, Florida Keys
    1 / 6
    5 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex & The... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    MINIMUM STAY: 29 DAYS LYONS LANDING is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and... View all property information
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    Islamorada, Florida Keys
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' If you are looking for gold sinks, with gold fixtures, this is not the place for you! This is a place to just 'hang out' while savoring the ocean view, breezes and sounds. If you want peaceful, secluded and close to nature... View all property information
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    Islamorada, Florida Keys 33070
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    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    The Hippie Home was Built with Love in the Sunshine of the Spirit. Nestled in Islamorada, the Sportfishing Capital of the World. The Neighborhood is Quiet and Pet Friendly with a Private Beach and Tiki Hut. Close to Restaurants, Shopping, Recreation, Fishing Charters, Scuba Diving, and Snorkeling.... View all property information
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    Islamorada, Florida Keys 33036
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    4.5 of 5 bubbles (7) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    Islamorada, Florida Keys 33036
    1 / 34
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    Welcome to paradise! Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous ocean views from every room. Built using ICF... View all property information
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    Islamorada, Florida Keys 33036
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. 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 property. Make your self at home in our home away from... View all property information
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    Islamorada, Florida Keys 33070
    1 / 21
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    About this property
    WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you. View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 28
    5 of 5 bubbles (30) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking... View all property information
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    Islamorada, Florida Keys 33036
    1 / 44
    2 of 5 bubbles (2) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay.<BR><BR>Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget... View all property information
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    Islamorada, Florida Keys 33036
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing views of the Clear Blue... View all property information
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    Islamorada, Florida Keys 33036
    1 / 6
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a... View all property information
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    Islamorada, Florida Keys 33070
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    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride... View all property information
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    Islamorada, Florida Keys
    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
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    Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled in 2014/15 so everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! A brand new luxury heated pool / spa was added in 2015 and is surrounded... View all property information
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    Islamorada, Florida Keys 33036
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    1 / 68
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    ***** Amazing Home For An Amazing Price Through January 31st, 2017 Live your tropical dream at this palatial oceanfront estate that is newly available through Freewheeler Vacations. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about... View all property information
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    Islamorada, Florida Keys 33070
    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 / 13
    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
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
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    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 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100 concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 20
    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
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    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
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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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    • x
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    Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings and the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
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    Islamorada, Florida Keys 33036
    1 / 26
    4.5 of 5 bubbles (8) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile... View all property information
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    Islamorada, Florida Keys 33036
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    BEAUTIFUL GATED OCEANFRONT ESTATE! Located on almost 2 acres in Islamorada featuring amazing ocean views, 5 bedrooms, 3 bathrooms, winding interior staircase, expansive ocean view porches, over 4,000 sf of living space, pool, sandy back yard, gated entrance, and beautiful soaring palm trees that... 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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    *** 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 / 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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 36
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
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    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room).  Screened in porch of the living room.  There is 70' of dockage.  Easy ocean or bay access via Snake Creek.  Walking distance to... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Parking
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 / 29
    5 of 5 bubbles (23) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    • Grill
    • Patio
    • Satellite TV
    • Air Conditioning
    • Washer
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 35
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a... View all property information
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    Islamorada, Florida Keys 33036
    1 / 37
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
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    Beautiful 2 bedroom 2 bath, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and this unit has ocean views. Some... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 99
    10 Bedrooms, 10 Bathrooms, Sleeps 28 | Quick View
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    • x
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    Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 20
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Washer
    • Waterfront
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Central Heating
    • Washer
    • Ocean Views
    • DVD Player
    • Terrace
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    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 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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