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House Rentals and Cottages in Islamorada, FL

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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    MINIMUM RENTAL 1 MONTH: Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting... View all property information
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    Islamorada, Florida Keys 33036
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    House has access to all water recreational activities , and yet secluded enough to feel you are all alone in Paradise , you can have your boat dockside (50'dock) gas and full service marinas less than 3 minutes away by water, dockside gas service available. The Florida Keys can be considered the... View all property information
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    Islamorada, Florida Keys 33070
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful professionally decorated condo in Futura Yacht Club. Pool, club house, Tennis, Marina with great fishing. Marker 88 restaurant is a short paddle board away. Private beach with sun set view. Perfect location near everything, restaurants, bars, shopping. Diving centers ,fishing, boat... View all property information
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    Islamorada, Florida Keys 33070
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    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 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    MINIMUM RENTAL 1 MONTH: 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 Reef and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 full bath. To the right is a large bedroom with a king bed and full bath. The laundry area with a full size washer and dryer is also located in this room. To the left of... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    <b> Minimum Rental: 1 Month </b> This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look at the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 6
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • Elder access
    • 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
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed November 18, 2014
    Just wanted to thank Bill for a wonderful four days at his place. Condo has tremendous views -- you are on the top floor -- amenities are great as well as the sleeping...
    4 of 5 stars Reviewed July 7, 2014
    The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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    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 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $5,250
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    About this property
    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 / 21
    5 of 5 stars (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • x
    • ?
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    • Elder access
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    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 4 weeks ago
    The Lobinskys, the owners, were responsive, informative, and extremely helpful. We traveled as a family with our two teenagers and our boat. Chris and Deanna provided options...
    5 of 5 stars Reviewed December 1, 2015
    Very well appointed. Comfortable. Pool, hot tub and grounds are very well kept. Owners are easy to work with. We hope to stay again next year!
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    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $4,500
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    • Patio
    • Porch
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    • Pet-friendly
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    • x
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    About this property
    Great 3 bedroom and 2.5 bath home located in Lower Matecumbe at mm73 on the ocean side. This adorable home as great outdoor space including a jacuzzi and upper level deck and lower level patio to relax in. Inside home has great open floor plan with a ground floor bedroom and bath along with 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 36
    4 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 2, 2014
    This is a great vacation rental property for a couple or small groups of 4 or less people. First of all, you can't beat the panoramic view of the water and what's more, the water...
    4 of 5 stars Reviewed April 13, 2014
    This house so reminds me of my grandparent house. The décor and appliances are pretty outdated but functional. It's full of quirky decorations and pictures that are fun. Seeing...
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    1 / 19
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    No short term stays (under 28 days) Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful 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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 3 weeks ago
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
    5 of 5 stars Reviewed August 28, 2015
    My husband, our three boys (21, 15, 12) and myself stayed in this property as a respite after visiting the parks in Orlando. The house is comfortable, well equipped and looked...
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Yard
    • Balcony
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    • Terrace
    • Private Outdoor...
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    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed September 9, 2015
    Enjoyed my 2 night stay. Bombay room was quiet, uniquely furnished, clean, and well-air conditioned. Refreshing pool and nice seating areas with plantings, water features, and...
    5 of 5 stars Reviewed July 26, 2015
    This cute place was a perfect stop on a little crawl down the keys I planned for me and my mom. I loved the garden and rooftop patio. Very good service and hosts. Thank you Mrs...
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    1 / 30
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    5 of 5 stars Reviewed March 25, 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the new...
    4 of 5 stars Reviewed June 5, 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    <b> Minimum Rental: 1 Month </b> Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your... View all property information
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    Islamorada, Florida Keys 33036
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 33036
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 Club is located in Islamorada, the Sport Fishing Capital of the World.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    • x
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    • x
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    About this property
    <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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed August 23, 2013
    My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could...
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    1 / 18
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $2,200
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    • Pet-friendly
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    • Child-friendly
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    About this property
    <b> Minimum Rental: 1 Month </b> Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed September 14, 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me. The...
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    1 / 27
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $3,220
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    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 courts, a swimming pool, a clubhouse, a private beach and a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed May 1, 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    5 of 5 stars Reviewed March 28, 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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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
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 stars Reviewed April 10, 2015
    Overall this was a good choice for our 2 week stay. We were within reasonable distance from both Key Largo and Marathon, and there were numerous attractions and activities close...
    4 of 5 stars Reviewed August 3, 2014
    Nice townhome with water view, easy drive to activities in Islamorada, Tavernier, and Key Largo. Townhome is 3 levels, lots of stairs, narrow staircases. Clean, updated, kitchen...
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    1 / 31
    5 of 5 stars (21) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
    • Children's Pool
    • Satellite TV
    • Ocean Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed August 28, 2015
    Great condo, great location. Private beach was really nice. Richard was amazing. Really enjoyed ourself!
    5 of 5 stars Reviewed August 18, 2015
    Our son went to Boy Scout Camp out of Islamorada and my husband and I stayed here several days just the two of us and several days with the three of us (my husband, myself, and...
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    1 / 49
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $3,255
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    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 13, 2014
    We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
    5 of 5 stars Reviewed April 16, 2014
    House and property were exactly as represented. Excellent communication by owner and everything went perfectly. Multiple balconies and plenty of areas to soak up the sun or...
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $147
    / Night
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    • Terrace
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Washer
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    MINIMUM STAY 1 MONTH: 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 spacious... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $3,000
    / Month
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    • Terrace
    • Parking
    • Satellite TV
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed August 13, 2014
    Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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    1 / 20
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    From
    $467
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    • Internet Access
    • Patio
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    • Private Outdoor...
    • Waterfront
    • Air Conditioning
    • Porch
    • Balcony
    Suitability
    • Pet-friendly
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    About this property
    This is a 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 This home only rents monthly!!!!! Beds: 2 King Beds, 2 Queen Beds, 1 Double Bed, 2 Twin Beds View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    $2,300
    / Month
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    • Grill
    • Shared Outdoor Pool...
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    • Hot Tub
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    About this property
    <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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed February 13, 2015
    This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had...
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $3,200
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    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Hot Tub
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, and tray... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $175
    / Night
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Balcony
    • Patio
    • Terrace
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM RENTAL 1 MONTH: Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally 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 33036
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $2,300
    / Month
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    • Satellite TV
    • Hot Tub
    • Shared Outdoor Pool...
    • Grill
    • Balcony
    • Patio
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    About this property
    <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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 50
    4 of 5 stars (18) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    $5,300
    / Week
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    • Internet Access
    • Grill
    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed January 2, 2016
    The view of water was spectacular the pool was perfect we had a barn fire in there fire pit on our private sandy beach. The balconies were mind blowing and it was the best week we...
    4 of 5 stars Reviewed March 5, 2015
    We traveled to Islamorada during late January-early February. This house was lovely and had been recently undated. The staff who took care of the house were nice and immediately...
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $5,250
    / Month
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    • Parking
    • Patio
    • Balcony
    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Terrace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    <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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed July 15, 2013
    This place delivers. You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is...
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $1,500
    / Night
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 24, 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $142
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    • Ocean Views
    • Balcony
    • Satellite TV
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    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby.... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $6,000
    / Month
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    • Parking
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
    • x
    About this property
    Spacious 3/3 canal front home in Lower Matecumbe. 75 Ft of dock with 45 FT cut-in for extra boat protection. Walk down the street to world famous Robbies for dinner/drinks and boat, kayak and jet-ski rentals. Located on MM 77, this place is close to many restaurant and tourist sites. Just a few... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $117
    / Night
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    • Patio
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Internet Access
    • Washer
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Wonderful two story townhome in a private, gated community with all amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60 inch... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    other travelers have booked this property
    From
    $475
    / Night
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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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. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $100
    / Night
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    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM RENTAL 1 MONTH: 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 share... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $1,395
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    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
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    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
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    About this property
    <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
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed October 5, 2015
    We came for 10 days to celebrate my husband's 70th birthday. Wow! The views from the balcony and in three directions - all onto the water - were amazing. Gorgeous...
    4 of 5 stars Reviewed June 1, 2014
    Having stayed in other properties at Futura Yacht Club over the years, I can honestly say that this was by far the nicest. The kitchen had been recently renovated with new white...
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    1 / 49
    5 of 5 stars (13) Excellent
    10 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
    From
    $12,000
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 7, 2015
    Great location. Very clean and relaxing. If you are looking for a waterfront view, this place does not have it but it is only a very short walk down to the dock to have a...
    5 of 5 stars Reviewed October 17, 2014
    We stayed at the Alligator Reef Luxury estates as a group of 18 people. This was a business gathering to bring our team together from all over the world, and this estate couldn’t...
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $3,000
    / Month
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    • Waterfront
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Summer Seas is located directly on the Florida Bay is the perfect sunny getaway! The complex is centrally located at mm 88. There is also on-site community laundry, a pool, hot tub, and clubhouse. Islamorada, the 'Village of Islands,' is widely known as the sportfishing capital of the world. Its... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 28, 2014
    We'd like to thankBrandi, Amy, and Kim for all their hard work and kindness. Wonderful people to work with. The condo was everything described and more. Beautiful view and...
    5 of 5 stars Reviewed August 23, 2011
    Rented a 2/2 condo for the month of July 2011. Great location, nice amenities,clean,wonderful view, friendly staff and condo owners. Excellent price. I will definitely do this...
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    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $3,000
    / Month
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    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    'Cute & Keysy' perfectly describe this Conch home! Located in the Tollgate Shores subdivision of Lower Matecumbe (south Islamorada), this delightfully quaint home has lots of character, charm, and is well-maintained. You'll enjoy sea breezes and the smell of salty air coming through the windows of... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $185
    / Night
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    • Waterfront
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Located at mile marker 76 overlooking a beautiful canal leading to the Atlantic Ocean. Boat slip available for the adventurous types. Kayaks for those wanting to explore the local mangroves. Borrow a bicycle and peddle your way through the lower matecumbe via bike path. Don't forget to visit... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, Sleeps 4 | Quick View
    From
    $3,000
    / Week
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    • Air Conditioning
    • Wi-Fi
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    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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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 33036
    5 of 5 stars Reviewed September 15, 2015
    The pool, the point, the palms...Great fishing with the kids and snorkeling for the big kids! Dozens of Iguanas to provide entertainment, too. We were all blown away with this...
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