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CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...
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An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique...
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The location, pool and setting were spectacular. The condo was clean and had everything we needed. Highly recommend.
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*TOP 1% HOME* GUEST FAVORITE* This Key Largo 4 BED/ 4 BA Trendy & Modern Home is just steps to 2 Oceanfront Pools, Pickleball, Jacuzzis, BYOB Speakeasy Game Room, Tennis & Basketball Courts and Marina. A Coffee Bar, Private Balconies, Instagram LED Photo Wall and private en-suite baths await your...
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Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan...
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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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Key Amenities
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Private canal-front home designed for 27+ day stays, offering a quiet, comfortable alternative to high-turnover vacation rentals. Private dock, heated/chilled pool, and just 3 minutes to open water—ideal for boating, fishing, and extended stays. Seasonal summer rate currently offered due to availability.Set...
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Hi, nice to meet you!!! If you like to be somewhere surrounded by a magnificent peace and balance, fresh, organized and a very clean home, "you just found it". You will be happy to go out in the boat and come back to a relaxing home to enjoy the rest of the day with family or friends with...
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Construction Notice – La Brisa Condominium March 2, 2026 through, May 1, 2026 (East Building) Construction is underway in the East Building to repair walkway spalling. Some construction noise may occur during your stay.Elevators are currently unavailable due to repairs and modernization. Access...
Featured review
Very thing was good the condo was perfect and the pool was great the parking was close to the elevator
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PROPERTY NAME: Twice the Charm 214 S. Ocean Shores Dr, Key LargoLOCATION: Oceanside Canal Front HomeMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 98.5DETAILS: "Twice the Charm" is a gorgeous newly remodeled single family...
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Coastal décor greets you in this two bedroom two bathroom Oceanfront Condo in Building 3. The comforting living room features a flat screen TV, and sliding glass doors that open to the step-out balcony offering sweeping views of the Atlantic. Visit delicious local restaurants or create amazing...
Featured review
I’ve stayed here multiple times and it is always very clean and smelling great! The AC is always kept low and feels great walking in after being out in the Florida heat. PLENTY of things to do and plenty...
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Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station.Master Bedroom has a queen size bed, shower and indoor jacuzzi tub. Second...
Featured review
Alex and I had a wonderful time in your beautiful home. Loved eating dinners (breakfast and lunch too!) sitting outside. Peaceful and lovely. The storage room downstairs was perfect for storing all our...
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Tropical Oasis on the Canal: Tiki Bar, Heated Pool & Outdoor Grills Big Pine Key, FL | 5 BR, 3 BA | 28-Day Minimum Stay Escape to the ultimate Florida Keys retreat! This expansive, fully fenced canal-front estate offers a resort-style experience designed for families and groups seeking privacy,...
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Villa, 4 Bed + Convertible bed(s), 3.5 Baths (Sleeps 6 - 10), Free Secure WiFi! An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction...
Featured review
This was a great location to celebrate my husband's 60th birthday with our adult children and significant others. The condo was conveniently located in Key Largo and the grounds were well maintained and...
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Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...
Distance to beach: 10 miles to Bahia Honda
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Welcome to Paradise Palms! This amazing 3 bedroom home on Cudjoe Key is perfect for your next Florida Keys vacation! Tropical landscaping surrounds an inground pool that overlooks a beautiful canal...everything you could want and more! There is also large concrete dock for your boat, quick easy ocean...
Featured review
My family and I stayed for the month of June 2022 and this was the first time we had visited Cudjoe Key. The house was beautiful and VERY clean. The kitchen was well equipped with everything you needed...
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Available for the 2026 season! (weekly rentals permitted) Affordable piece of paradise! Escape the cold and come enjoy this Venture Out home with open concept, bright and airy rooms, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you’ll be amazed. This fully furnished home...
Distance to beach: 5 miles to Smathers Beach
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3 bedroom 2 bath home, heated / chilled pool, plenty of parking for trailers / boats / on a deep water canal with a view to die for. Our home is fully fenced with a large gate opening to enter with your boat trailers etc. (Two king size beds and a full size bunk on the bottom and a twin on top. We...
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Beautiful house in Big Pine Key, Fl on the water. Bring your boat and have it in the water in the back of the house. Comes with everything needed for your amazing stay. There is an ice maker for your use as well. Also you are only 30 miles away from the world famous Key West.
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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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This unit (2) is located on the second floor with access through no elevator. Staircase in front of building with spiral staircase in back of building. It is a furnished 2 bedroom, one bath unit. There is a clothes washer and dryer laundry room on property premises. This unit is very well equipped.Minimum...
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The Conch House is a very special little piece of paradise located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard!! It sits on the open water on Pine Channel on the Gulf side of the Keys. The newly constructed cement L shaped dock can accommodate up to a 32’...
Featured review
House was great, nice layout, pool and view. We had a wonderful time. I would have liked a dock to fish in deeper water from, more reeks and grass beds here. Beautiful though, great host
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Escape to Key Largo and experience the ultimate Florida Keys getaway! Whether you're looking for a family vacation, a trip with friends, or a peaceful retreat, this newly remodeled 4-bedroom, 3-bathroom home offers the perfect setting to relax, explore, and make lasting memories.Key Features:Spacious...
Featured review
We stayed in this home for a month and we had a wonderful time. The home is very spacious with 4 bedrooms and 3 bathrooms. It is remodeled and it has 2 family rooms. It had space for my boat and parking...
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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.
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Welcome to Dockside, your perfect keys getaway! Nestled in a serene location, Dockside offers a fully furnished retreat designed to make enjoying paradise effortless!Dockside is a fully equipped home; featuring a spacious and comfortable living space, a kitchen with all you need to prepare the day’s...
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This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs...
Featured review
This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki...
Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park
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SUMMER/FALL SPECIAL. $500 OFF MY RATE. So welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two-bedroom,...
Featured review
A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area...
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Welcome to Blue Wahoo, the perfect Florida Keys Island Getaway.Check-in to this gorgeous coastal home for a wonderful vacation on what is arguably the nicest of Florida’s lower keys. This house has it all. It is beautifully furnished; from a well-equipped kitchen and updated living room to...
Distance to beach: 0.5 miles to White Marlin Beach
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*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will...
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CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...
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Welcome to your ideal vacation getaway in the heart of the Florida Keys! Located in the serene Cudjoe Key, this charming home offers luxurious amenities and a perfect blend of comfort and style. Imagine waking up in a cozy, beautifully decorated home and enjoying your coffee on a private deck surrounded...
Featured review
This was the best vacation I have ever had in Florida. The house was beautiful and it was very peaceful sitting out on the canal. Only 20 miles to Key West makes for easy day trips. We went 5 times! The...
Distance to beach: 0.9 miles to Founders Park
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Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom...
Featured review
We spent a month in Sharon's condo (January 2025). Upon arrival we had everything we needed for the month! She goes above and beyond stocking the kitchen, cleaning supplies, pantry etc. The bedrooms are...
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Private Beach, ocean front home with pool on Cudjoe Key.Home includes;- Master bedroom suite with 32' flat screen TV, full bathroom including tub and shower for 2, sliders open to private Master Suite deck with ocean view and private beach.- 2 additional bedrooms with Jack-n-Jill bath-...
Featured review
We really enjoyed the large house. The easy to launch kayak area was very convientant. Location was great - 25 minutes to Key West. The sunsets were breathtaking. House was well equipped with every you...
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This is one of the most unique homes in all of the upper keys! What makes it special is that it's located on a peninsula so very private while at the same time offers stunning views of the Key Largo Bay.The home was recently updated to include all new flooring, new stainless steel kitchen appliances,...
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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...
Distance to beach: 2 miles to Founders Park
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*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...
Distance to beach: 0.5 miles to Key Colony Cabana Club Beach
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Beautiful 2-story half duplex home on wide canal with boat slip. Sleeps 10 comfortably. 4 bedrooms, bathrooms and lower-level family room with mini kitchen make this a great place for multiple families to have private space or gather together.Plenty of parking for boat trailer and multiple vehicles,...
Featured review
INTERESTING LOCATION on an active canal in Key Colony Beach…Lots of space and privacy for a group of eight.Can accommodate ten.Good parking and boat accommodation.GARAGE WITH TONS OF STORAGE AND SECURITY..private...
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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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This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. In minutes you can explore the beautiful back country or Ocean by kayak or boat. Marine Life sightings and fishing is the best in this area. You can lay back and relax, away from it all and...
Featured review
Friendly neighborhood!! Neighbors shared some fresh fish they caught. We loved taking a walk morning and evening to take photos of all the little key deer. Walked to the neighborhood private park to watch...
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Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor...
Featured review
I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described
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We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you...
Featured review
Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.
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...
Distance to beach: 1 miles to Sombrero Beach
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Beautifully updated 3 bedroom, 2 bathroom stilted home on exclusive Flamingo Island in the high-demand Sombrero Beach area. This home will not disappoint. Fantastically lush and meticulously landscaped yard by local famous design artist featuring a large, brand new heated/chilled pool with plenty of built...
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CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information....
Featured review
BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO...
Distance to beach: 2 miles to Sombrero Beach
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Gorgeous crystal clear, open water views of the Gulf of Mexico, incredible sunsets. Deep Water Dockage for your boat, snorkel, fish or dive right from the dock.This is not your typical canal home that are rented throughout Marathon. This one has open water, privacy and an un-obstructed view. This...
Featured review
Absolutely great place to stay. Clean, comfortable and fantastic views. Would rent again. Highly recommend.
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Island Tropical Bungalow! This lovingly maintained, delightful and spacious 3/2 with large expanded porch and Boat ramp just crossing the street makes a great getaway. All utilities are included (water, power, wifi, tv) Large shed in back with laundry (washingmachine and dryer). Totally redone...
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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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The Shores of Sugarloaf Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and SunsetsWelcome to the Shores of Sugarloaf, the perfect Florida Keys Island Getaway. Check-in to this gorgeous coastal home and enjoy a lovely vacation on one of the Florida Keys most desirable keys-Sugarloaf. This house...
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An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most...
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,...
Featured review
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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