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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 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    <b> Minimum Rental: 1 Month </b> Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony.... View all property information
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    Islamorada, Florida Keys 33036
    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 / 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 / 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 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 1 Month </b> You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located... View all property information
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    Islamorada, Florida Keys 33036
    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 33036
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    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 50 | Quick View
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    About this property
    jaouoroqoaueo9quoruroqwu9euour99n9n9r9wur9ue9adouafiuaeoufasljfaof0askr;oasd-fsd4fas8/da5se/xgv5asqe-0taa8asdg=as9ufaoefauoatwouoasujfgaseuroue9rtasofuoasuaweroasufoauf0aasf5asf6asf6as6f6aseoufawi9rayweriyawiywririyseiyaweiryqwiryiweykcasdyvkshvckcaicaeiycaiyaisyaivyiseyvaifyksdhfikzhfisadkasrhisdhf... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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 / 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 33036
    1 / 38
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    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 33036
    1 / 16
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights </b> Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights (Saturday to Saturday)</b> BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
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    Islamorada, Florida Keys 33070
    1 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This Property is fully insured for rentals and licensed by the Village of Islamorada, license #VR-228. Welcome to 134 Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated... View all property information
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    Islamorada, Florida Keys
    1 / 31
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Affordable Venetian Shores canal home at the Mile Marker 86, Bay-side. Nice decor, recently updated with a private downstairs apartment. Two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room). Easy ocean or bay access via Snake Creek.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 30
    4.5 of 5 stars (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
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 33036
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    This home features 4 bedrooms, 2 baths, pool and bar. This home can comfortably accommodate 8-10 people with room to spare. Alluring turquoise ocean and beachfront views. The onsite boat parking provided tremendous privacy and space for you and all of your guest. A private pool and grill that... View all property information
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    Islamorada, Florida Keys 33070
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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 33070
    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This is a newly remodeled 4 bedroom 2 bath private home on the ocean side (just 3 houses from the open ocean) with ocean views, pool, tiki hut ice machine and all the comforts of home. This home is perfect for family and fishing! Beds: 1 King Bed, 5 Queen Beds View all property information
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    Islamorada, Florida Keys 33070
    1 / 29
    5 of 5 stars (22) 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 33036
    1 / 49
    5 of 5 stars (14) Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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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
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    Islamorada, Florida Keys 33036
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | 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 &... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 33036
    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 70
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    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 every convenience you can imagine, as well as some you probably... View all property information
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    Islamorada, Florida Keys 33070
    1 / 20
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    This is a huge 6 bedroom pool home with direct dockage just off Snake Creek. Home has 2 kings, 3 queens, and 2 twins. Located at mile marker 86 on the bay side I only take payment by personal check made out to owner!!! Never a wire transfer!!! Please be careful. This home only rents... View all property information
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    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
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    Islamorada, Florida Keys 33036
    1 / 13
    16 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    About this property
    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 33036
    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 / 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Internet Access
    • Grill
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport and 86 miles from Key West. Venetian Tropics boasts large rooms furnished in rattan and decorated with a tropical flair. Coconut palms, hibiscus and other... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Porch
    • Internet Access
    • Patio
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 28
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Grill
    • Porch
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully... View all property information
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    Islamorada, Florida Keys 33070
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    • Balcony
    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
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    • Internet Access
    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Washer
    • Balcony
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    • DVD Player
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • Waterfront
    • Porch
    • Washer
    • Air Conditioning
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the spectacular view of the Florida Bay from this elegant, tasteful, completely remodelled townhome. 2 bedrooms, 2.5 bathrooms with balconies off the living room and master bedroom. Fully furnished and equipped for vacationers. Wifi and washer dryer in the unit. Very affordable dockage... View all property information
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    Islamorada, Florida Keys
    1 / 36
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Parking
    • Grill
    • Waterfront
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    • 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
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Waterfront
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around the house and... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • DVD Player
    • Private Outdoor...
    • Patio
    • Internet Access
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Two Oceanfront villas on two beautiful acres. It has a total of three bedrooms and two and half baths. Sleeps 8-10 comfortably. One King bed, two queen beds, two twin beds, and two queen size pull out sofas. Both villas have full kitchens, living area, lots of windows with gorgeous Ocean and beach... View all property information
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    Islamorada, Florida Keys 33036
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33070