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There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned with everything you'd need on vacation and...
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Oceanfront Islamorada Townhome with Private Dock, Pool & Sunrise ViewsWake up to panoramic ocean sunrises in Islamorada. This 3-bedroom, 3-bath oceanfront luxury townhome features a private dock, sandy entry for kayaks, and a resort-style pool just steps from your door.Your Keys EscapeSet...
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The property owners were extremely helpful in every way. If you can't have fun here, you just can't have fun.
Distance to beach: 2 miles to Anne's Beach
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House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large...
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See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler.The ONLY pool...
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1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community...
Featured review
Here is the review I am trying to post via for our March 2024 stay.Wonderful! Fantastic! Amazing!Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we...
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PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated...
Featured review
Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient....
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Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a grand open-concept layout seamlessly blending living, dining, and a wet bar, all framed by panoramic seascapes, a chef's kitchen and access to top-tier...
Distance to beach: 2 miles to Founders Park
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This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios...
Featured review
This was the nicest home overall I have rented. If you have a boat, don't look elsewhere. Everything in the house functioned and the house had everything one would need, even for people who do cook while...
Distance to beach: 3 miles to Founders Park
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Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...
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Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock...
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This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its tiki bar, expansive sandy playgrounds and lounge areas. Nestled along the tranquil shores of Florida Bay, its array of indoor and outdoor living areas, BRING YOUR BOAT - dock with ocean-access...
Distance to beach: 100 yards to Port Antigua Private Beach
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This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach.The house is nautically designed, with a spacious and open floor plan. There's a large...
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This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast....
Featured review
This is my first time staying in Islamorada for the many years I have been coming to the Keys, and I must say, I am fully addicted to Islamorada! Islamorada is just not as "commercial" as the middle keys,...
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Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of...
Featured review
We stayed here in the “Honu Hale” house in August 2024 during the Florida Lobster Season. The property is ideally laid out & set up for boaters, divers & fisherman. There’s plenty of dockage and a...
Distance to beach: 0.5 miles to White Marlin Beach
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Bring your boat!Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, and two floors facing the canal and a private sanctuary....
Featured review
We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has...
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Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home...
Featured review
Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows...
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PROPERTY NAME: Fisherman's Gem 113 Iroquois Drive Islamorada, FloridaLOCATION: Oceanside Canal home with Boat dock and Boat RampMIMINUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 74This waterfront, ground-level Islamorada home, featuring...
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Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter....
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PROPERTY NAME: Sunshine Place 84371 Overseas Highway, Islamorada, FLLOCATION: Oceanside HouseMINIMUM STAY: WeeklyMILE MARKER: 84.3DETAILS: "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing...
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PROPERTY NAME: Sandglass 4 74980 Overseas Highway #4, Islamorada, FLLOCATION: Bayside Town House Located in Lower MatecumbeMINIMUM STAY: 7 DaysMILE MARKER: 74.9DETAILS: ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada....
Featured review
Place was super - location decor and views- only issues we had were the a/c did not work well 1st 3 days and we couldn’t sleep in bedrooms even with fans- so the 3 nights we had to sleep in living area...
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Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends....
Featured review
We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the...
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Ocean side pool home with private dock. Beautifully decorated with 2 bedrooms and 2 bathrooms on the main level. Master bedroom has a queen size bed and a full bath. The second bedroom has twin beds. Downstairs is a suite with sleeping accommodations for 4 people and full bathroom. Linens and towels...
Distance to beach: 5 miles to Anne's Beach
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Welcome to The Nest Villa & Marina in the heart of beautiful IslamoradaNestled on a picturesque 1-acre lot overlooking the stunning Florida Bay in the Florida Keys, the Nest Villa offers a perfect blend of privacy and proximity. This exclusive residence is one of seven privately owned villas,...
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My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen!...
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The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove...
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PROPERTY NAME: Martin Family Fish Camp 106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each...
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Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also...
Featured review
This house is beautiful. Right on a canal where we kept our boat for the week. Manatees came by to visit daily. Caught keeper mangrove snapper right there. Neighbors were amazingly friendly. Everything...
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PROPERTY NAME: Villa Riolo 130 Columbus Drive, Islamorada, FLLOCATION: Gated Oceanside House on canalMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.5DETAILS: "Villa Riolo" is an updated single family stilt home and perfect...
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Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking...
Featured review
This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.
Distance to beach: 2 miles to Founder's Park
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Long-term rental available in the beautiful Venetian Shores community of Islamorada, Florida. This 3-bedroom, 2-bath home sits on a secluded plugged canal by the water. Enjoy a large master bedroom, a spacious open layout, and a generous outdoor deck ideal for entertaining. Additional features include...
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