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Villas and Holiday Rentals in Islamorada, FL

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    Travellers to Islamorada are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 19
    5 of 5 stars (6) 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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    1 / 22
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 1 January 2016
    I was already familiar with the building,boy have they done beautiful landscape upgrades!The condo has spectacular views,couldn't be better!.everything you could want/need is in...
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    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    €116
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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 9 September 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 26 July 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 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    €2,869
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    About this property
    *** 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
    Location Information
    Islamorada, Florida Keys
    1 / 21
    5 of 5 stars (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €231
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    • Child-friendly
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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 1 December 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 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, Sleeps 4 | Quick View
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    €2,690
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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 15 September 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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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    €3,138
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    • Child-friendly
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    • Elder access
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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
    Location Information
    Islamorada, Florida Keys 33036
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
    • Porch
    • Outdoor Dining Area
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    • DVD Player
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    • Balcony
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    €426
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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 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    €2,887
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    • Wi-Fi
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    • Balcony
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Beautiful two 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 townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 31
    5 of 5 stars (21) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    €2,600
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    • Waterfront
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Sauna
    • Children's Pool
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • 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 28 August 2015
    Great condo, great location. Private beach was really nice. Richard was amazing. Really enjoyed ourself!
    5 of 5 stars Reviewed 18 August 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 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 49
    5 of 5 stars (13) Excellent
    10 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    €10,759
    / Week
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 7 March 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 17 October 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 / 29
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    €2,241
    / Week
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    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 19 October 2011
    Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably...
    5 of 5 stars Reviewed 15 June 2011
    The house had some minor issues with things not working but it was addressed quickly. We loved the house and location on the bay. Great dockage for a large boat. Brandi at...
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    1 / 31
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €1,883
    / Week
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    • Washer
    • Satellite TV
    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 10 April 2015
    We had a wonderful time with the family fishing trip. The house is great, with grown sons the house is set up so everyone has privacey. The house is in a perfect location. The...
    5 of 5 stars Reviewed 9 February 2014
    Love the location, house was extremely well equipped, comfortable, Very accommodating to a wide range of taste and activities!
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    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    €4,707
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
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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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 28
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €3,138
    / Week
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    • Waterfront
    • Grill
    • Porch
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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
    Location Information
    Islamorada, Florida Keys 33070
    4 of 5 stars Reviewed 25 March 2015
    The house I rented is located in the Florida keys and was very nice. The managing agent, Freewheeler Reality, had the keys so I had to drive 2 miles past the house to get/return...
    5 of 5 stars Reviewed 20 February 2014
    Great home not fancy but with all the needed amenities, excellent location, had a great time with children and grand-kids
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    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €4,035
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    • Wi-Fi
    • Terrace
    • Washer
    • Waterfront
    • Grill
    • Balcony
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Come enjoy your very own get away in Port Antiqua with a spacious open floor plan, decorated with clean modern decor. 2/2 upstairs with a detached 1/1 downstairs. Located at the end of the cul-de-sac and the front of a canal with 155' dock-age available with fish cleaning station, and just a short... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €1,345
    / Week
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    • Waterfront
    • Air Conditioning
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    • Pet-friendly
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    • Child-friendly
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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 10 April 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 3 August 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 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    €4,931
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    • Private Outdoor...
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    • Waterfront
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    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 / 70
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    €31,380
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    • Patio
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    • Waterfront
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This ultimate gated luxury property that directly sits on the Atlantic Ocean is awaiting for your arrival. You will get swept away by three lusciously landscaped acres, fabulous views, beach area, observation deck over the ocean, and a tennis court. Located on exclusive Millionaires Row, Villa... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €4,035
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    • Patio
    • Porch
    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 / 30
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €2,062
    / Week
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    • Waterfront
    • Grill
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    • Pet-friendly
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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 25 March 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 5 June 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 / 24
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €1,793
    / Week
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    • Waterfront
    • Internet Access
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 7 August 2012
    We stayed here august 2011 with 2 other couples and fell in love with this place. We are here again now! This has plenty of room for the 6 of us. It is very clean. The...
    4 of 5 stars Reviewed 22 June 2012
    1st time wife has came with me to keys, she loved it and hopes to be back again. ty 4 the hassle free vacation
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    1 / 22
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €2,690
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    • Air Conditioning
    • Parking
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    From
    €3,586
    / Month
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    • Wi-Fi
    • Parking
    • Grill
    • Waterfront
    • Balcony
    • Air Conditioning
    • Washer
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This delightful 2 bedroom 2 bathroom with a detached 1 bedroom 1 bath downstairs is located on a quiet canal in Plantation Key at mile maker 90 ocean side. This home has a renovated kitchen and is beautifully decorated throughout. The property is fenced in and has amazing water views. You won't... 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
    From
    €1,345
    / Week
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    • Waterfront
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    • Pet-friendly
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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 2 May 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 13 April 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 / 50
    4 of 5 stars (18) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    €4,752
    / Week
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    • Internet Access
    • Grill
    • Waterfront
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 2 January 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 5 March 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 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    €4,035
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    • Air Conditioning
    • Grill
    • Parking
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    • Patio
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    €2,690
    / Month
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    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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
    1 / 30
    4.5 of 5 stars (8) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    From
    €2,690
    / Week
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 12 January 2015
    We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
    4 of 5 stars Reviewed 12 August 2014
    The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
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    1 / 5
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €1,479
    / Week
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    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 5 September 2013
    The Home and Location Was Perfect. The Only Problem Was One Of The Bedrooms Did Not Have a Mattress It Only Had The Box Spring. Everything Else was Great. Freewheeler Vacations...
    5 of 5 stars Reviewed 12 August 2013
    We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both...
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €3,407
    / Month
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    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    From
    €6,052
    / Week
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 35
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    €2,690
    / Week
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    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100 concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €2,008
    / Month
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    • Shared Outdoor Pool...
    • Grill
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    • Satellite TV
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 3 weeks ago
    This place was overall amazing! I had such a great time when I stayed here. I came along with my husband, two sons and daughter and we all had a phenomenal time! There wasn't...
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €4,035
    / Month
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    • Air Conditioning
    • Washer
    • Private Outdoor...
    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Great 2 bedroom 2 bath with a detached one bedroom apartment downstairs located in Plantation Key at mm 90. This home does have a private pool and is fenced in. Very comfortable home for your get-away. Stay for a month or multiple months. Close to restaurants and our grocery store. Please... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 20
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €4,035
    / Month
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    • Waterfront
    • Internet Access
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • x
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    About this property
    A very charming and immaculate 3 bedroom home in Plantation Key. This home has excellent protected deep water dockage. Ocean views from balcony. Easy bay access via Tavernier Creek. Close to resturants and store. CLICK HERE to view photos on a mobile device. Additional amenities include:... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 12 April 2014
    We love our little home away from home. It's a perfect location. Ocean view and water access. Everything we could ask for. We love our charming home.
    4 of 5 stars Reviewed 27 August 2013
    We needed a place on the ocean side that would accommodate our larger boat. This house was perfect! Location in between Snake and Tavernier Creek made it easy to access ocean or...
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    1 / 27
    4 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    €2,062
    / Week
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    • Washer
    • Satellite TV
    • Grill
    • Porch
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    About this property
    Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 5 September 2013
    House was great, close to everything, we really enjoyed the accommodations. It was a great set up. Negative would be all beds are very very firm and very very uncomforatable...
    5 of 5 stars Reviewed 20 August 2013
    Easy check in. Everything as described. Nice electronic lock on house so no need to keep up with keys. House was clean with great views. Everything you would need available. Would...
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    1 / 17
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €2,197
    / Week
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    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 25 March 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    5 of 5 stars Reviewed 19 January 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €2,690
    / Month
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    • Washer
    • Parking
    • Grill
    • Waterfront
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Please send us an inquiry or call us for availability. Prices vary on the units. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €2,869
    / Month
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    • Washer
    • Parking
    • Grill
    • Balcony
    • Satellite TV
    • Internet Access
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This charming 2 bedroom and 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store. This home offers deep water dockage and easy access to the Atlantic Ocean via Tavernier Creek. Great outdoor space whether you are sitting on... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €2,690
    / Month
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    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 stars Reviewed 14 April 2011
    We loved the comfortable two bedroom plus home. Perfect for us and our pet. Nice fenced in yard with a great fishing dock, parking port, outside bar with water and ice maker...
    4 of 5 stars Reviewed 23 February 2011
    Very nice...my 3rd time renting the house...no problems...excellent service...great location...I would recommend to others...hope to be back soon...
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    €2,690
    / Month
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    • Waterfront
    • Shared Outdoor Pool...
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 28 March 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 23 August 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 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    €2,510
    / Week
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    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 27
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    €2,887
    / Month
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    • Patio
    • Grill
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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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 1 May 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 28 March 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 / 26
    4 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    From
    €5,648
    / Month
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    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Water Front home, located Oceanside in Lower Matecumbe key, Islamorada mile marker 73, (The Sport Fishing Capital of the World). 15' wood dock and 12’ wide ramp, so bring your own boat and enjoy the sun!! Easy canal access to the ocean. (Maximum Boat Size: 27' include space at front of the ramp).... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 27 October 2015
    This house was absolutely great! I loved that it had a dock and I was able to bring my boat with me instead of having to leave it at a marina. I stayed here for a week with a...
    5 of 5 stars Reviewed 23 December 2014
    Great place. Loved the channel access in the back. We used our boat every day and it was great being able to keep it docked back there. The house was clean and comfortable. we ate...
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    1 / 27
    5 of 5 stars (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    €3,264
    / Month
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    • DVD Player
    • Wi-Fi
    • Washer
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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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 townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 17 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple. Due...
    4 of 5 stars Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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