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Villas and Holiday Rentals in Islamorada, FL

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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal.... View all property information
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    Islamorada, Florida Keys
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    <b> Minimum Rental: 1 Month </b> Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator... View all property information
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    Islamorada, Florida Keys
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    Relax and Unwind in Your Luxuriously Renovated Condo With Oceanfront Views in the Fishing Capital of the World: Islamorada!! Beautiful Open Water Views in a Well-appointed Building That Provides Everything You Need for a Relaxing and Memorable Vacation. the Cozy Patio Invites You to Enjoy Your... View all property information
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    Islamorada, Florida Keys
    1 / 13
    16 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    Casa Morada is an upscale sixteen suite privately owned hotel inspired by the informal character of the Caribbean. The atmosphere is private, peaceful, and serene. The staff is renowned for their warmth and attentiveness. We have 11 suites in our Garden House and 5 suites in our Seaview house. The... View all property information
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    Islamorada, Florida Keys
    1 / 27
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights </b> 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... View all property information
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    Islamorada, Florida Keys
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... View all property information
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    Islamorada, Florida Keys
    1 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights </b> Upper 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. This is one of 3 separate units for rent by the week or month. Each... View all property information
    Location Information
    Islamorada, Florida Keys
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    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    *** 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
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    <b> Minimum Rental: 1 Month </b> Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2... View all property information
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    Islamorada, Florida Keys
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely... View all property information
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    Islamorada, Florida Keys
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    <b>Casa Dorado</b> is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal areas. With the green roof... View all property information
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    Islamorada, Florida Keys
    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 32
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    This is a great 1 bedroom and 1 bathroom at the Sea Gulls Complex. This unit is located on the 6th floor and has amazing views. This unit is a decorated nicely and will be a perfect home away from home. The complex is located at mile marker 90 and has a pool and a kayak ramp. Sea Gulls Complex... View all property information
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    Islamorada, Florida Keys
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    <b>MINIMUM STAY: 29 DAYS</b> <b>LYONS LANDING</b> 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... View all property information
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    Islamorada, Florida Keys
    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 1 Month </b> Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the... View all property information
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    Islamorada, Florida Keys
    1 / 29
    5 of 5 stars (23) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    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
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    Islamorada, Florida Keys
    1 / 23
    3.5 of 5 stars (2) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    <b> Minimum Rental: 1 Month </b> Location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is... View all property information
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    Islamorada, Florida Keys
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;... View all property information
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    Islamorada, Florida Keys
    1 / 39
    5 of 5 stars (28) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application.... View all property information
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    Islamorada, Florida Keys
    1 / 21
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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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
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    Islamorada, Florida Keys
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b>MINIMUM STAY: 29 DAYS</b> <b>FISHERMANS PARADISE</b> 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... View all property information
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    Islamorada, Florida Keys
    1 / 25
    2 of 5 stars (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
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 28
    5 of 5 stars (30) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home... View all property information
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    Islamorada, Florida Keys
    1 / 28
    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
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Half Duplex Home Are you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and... View all property information
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    Islamorada, Florida Keys
    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
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    MINIMUM STAY: 28 DAYS <b>NEW LISTING - Available this winter!</b> But Hurry… this home promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this... View all property information
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    Islamorada, Florida Keys
    1 / 26
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    This newly remodeled & renovated (in 2012), two bedroom, Sea Gulls Condo unit, located on the ocean side of Plantation Key at Mile Marker 90, has an awesome view! Unit is comfortably and stylishly furnished, has TVs in the living room, two queen beds and a sleeper sofa. Sea Gulls has a nice pool,... View all property information
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    Islamorada, Florida Keys
    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
    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map<BR><BR>Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6<BR><BR>122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West.... View all property information
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    Islamorada, Florida Keys
    1 / 6
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,... View all property information
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    Islamorada, Florida Keys
    1 / 27
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 29
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless oasis over a full size lap pool. Lay down in the shade on the soft grass bordering the pool and enjoy... View all property information
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    Islamorada, Florida Keys
    1 / 25
    5 of 5 stars (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    *** 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
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
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    • x
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    About this property
    MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters,... View all property information
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    Islamorada, Florida Keys
    1 / 10
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Private Garden
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    • x
    • x
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    • x
    About this property
    Tarpon House at Bonefish Bay is one of 12 homes located in Islamorada's premier gated community. Each home features a private pool and hot tub, and guests are welcome to enjoy the common amenities such as beach, tennis court and playground. The house comes with kayak, paddleboard, and bicycles.... View all property information
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    Islamorada, Florida Keys
    1 / 25
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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
    1 / 15
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
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    Islamorada, Florida Keys
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys
    1 / 49
    5 of 5 stars (14) Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    • ?
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    • x
    About this property
    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
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    Islamorada, Florida Keys
    1 / 37
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    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
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    Islamorada, Florida Keys
    1 / 11
    4.5 of 5 stars (5) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys
    1 / 36
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Please send us an inquiry or call us for availability. Prices vary on the units. 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 courts, a swimming pool, a clubhouse, a private beach and a... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 26
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Satellite TV
    • Washer
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    • Grill
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to SOL Y MAR SOL Y MAR offers 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. The Property is located in the Center of the Florida Keys, Tavernier, 1.5 Hours to Miami, 1.5 Hours to Key West; Shopping, Restaurants, Theaters, Sunset Cruises, Diving,... View all property information
    Location Information
    Islamorada, Florida Keys