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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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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 / 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 / 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 / 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 / 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 / 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 / 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
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    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 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 / 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 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    *** Note: All rental rates are subject to 12.5% tax, $100 Processing Fee, $500 Security and a Variable Cleaning Fee and subject to change during the holidays *** View all property information
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    Islamorada, Florida Keys 33070
    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 / 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 / 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 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every... 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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    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
    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33070
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    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 / 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 / 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 / 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 33036
    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 50 | Quick View
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    jaouoroqoaueo9quoruroqwu9euour99n9n9r9wur9ue9adouafiuaeoufasljfaof0askr;oasd-fsd4fas8/da5se/xgv5asqe-0taa8asdg=as9ufaoefauoatwouoasujfgaseuroue9rtasofuoasuaweroasufoauf0aasf5asf6asf6as6f6aseoufawi9rayweriyawiywririyseiyaweiryqwiryiweykcasdyvkshvckcaicaeiycaiyaisyaivyiseyvaifyksdhfikzhfisadkasrhisdhf... View all property information
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    Islamorada, Florida Keys 33070
    1 / 38
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 / 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 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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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 / 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 / 28
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    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 / 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 / 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 / 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 33036
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • 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
    1 / 40
    4.5 of 5 stars (8) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. 2 bedroom/2 bath Keys house surrounded by a white picket fence with tropical fish mailbox...very "Keys-y"! The bedrooms are located on separate sides of the home with the common areas in between. There is deep water dockage... View all property information
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    Islamorada, Florida Keys 33036
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • DVD Player
    • Grill
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    • Washer
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    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • 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
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    • x
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    • x
    About this property
    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room , balcony, and the community's two tennis courts, along with two bedrooms, both with... View all property information
    Location Information
    Islamorada, Florida Keys 33070
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • Satellite TV
    • Patio
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    • 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 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • DVD Player
    • Grill
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    • 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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    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • 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
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    Islamorada, Florida Keys 33070
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Patio
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    • Internet Access
    • Air Conditioning
    • Grill
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This unit is a duplex with 2 full Bedrooms and 2 full Baths - plus a loft in the master bedroom that sleeps an additional 2. There is also an electric EZ Bed for larger groups. Also included is a gas BBQ Grill in the back porch and use of any of the recreational items at the unit. Located in the... View all property information
    Location Information
    Islamorada, Florida Keys 34950
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Private Outdoor...
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    • Satellite TV
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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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Internet Access
    • Grill
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 46
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Terrace
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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. The condo boasts some amaizing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats... View all property information
    Location Information
    Islamorada, Florida Keys 33036