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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....
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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...
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...
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Great location for keeping a boat, fishing, and visiting adjacent Keys! The Host was attentive and helpful with information regarding the area. Living space was clean and comfortable. Boat docking and location...
Distance to beach: 2 miles to Smathers
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28 minimum nights required by city of Key west. New listing-One level home! Relatives have stayed and loved it. Rates: October $9,000, November is $16,000 /month, December $18,000/month, January, 2027 $21,000/month, February $23,000/month, March $23,000 per month, April, 2027 $17,000 per month, cleaning...
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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Beautiful 3-BR house located directly on canal with easy access to the Gulf of Mexico or Atlantic Ocean. On-property pool and private outside shower. 75-ft dock for boat. Home of the Key Deer and Blue Hole (the deer will walk past house daily).Located 35 miles north of Key West, and 20 miles south...
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Welcome to "Sol y Sal" in Buttonwood Bay. Brand new 2 bedrooms + den/ 2 1/2 bath townhouse. This unit was just redone in 2024 and includes fantastic, high-end finishes. Spacious living room with 70 in. tv, dining room with seating for 8, and kitchen with stainless steel appliances, and powder...
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Off the HookImagine your vacation in this stunning custom-built modern 3-bed, 3-bath pool home, "Off the Hook," on the edge of Marathon. This newly built Florida Keys retreat welcomes you with a striking foyer and floor-to-ceiling windows that blend indoor luxury with outdoor beauty.The...
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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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Florida Keys Vacation Rentals – This waterfront home located in Coral Shores Park on Little Torch Key. It is a real paradise pleaser! The spacious interior is nicely decorated and completely remodeled. It has a beautiful open floor plan with views of the expansive deck and open water.There are...
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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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Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home...
Featured review
Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This...
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3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2...
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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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Looking for a home away from home? Via Villa is the place! This vacation home is located in Cudjoe Gardens on Cudjoe Key, only 20 miles from Key West. Situated on a corner canal, there is ample dockage for large boats, water and electric on the dock, as well as a waterside fish cleaning table. Via Villa...
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Available starting July 1, 2026. Extremely rare for Key West: Oceanfront property with dock and swimming pool. Have your cake and eat it too! 10 minutes to famous Old Town and its many entertainments, or to luxurious Perry Hotel and Marina, or to famous Safe Harbor Marina with Artists studios and Hogfish...
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Pool & Jacuzzi Resurfacing NoticePlease be advised that the pool and jacuzzi area will be closed for resurfacing beginning: July 6th – August 30th (weather permitting)The entire pool and jacuzzi area will be fully closed off during this time to allow the contractor to safely complete...
Featured review
Very thing was good the condo was perfect and the pool was great the parking was close to the elevator
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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Bahia Azul, "Bay of Blue" is exactly the perfect spot for your next Florida Keys adventure. The open water views are just stunning and spectacular. Its location at the end of the street makes this a very private get-away.This large home will accommodate all your friends and family with 4...
Distance to beach: 3 miles to John Pennekamp State Park
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Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...
Featured review
Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.
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This property is located on a very unique spot. Very private. Too perfect to describe.During the day you could sunbathe while fishing for snappers, tarpon and lobsters from your private dock. Later on you may want to jump in for a swim or cruise the area on the kayak At early evening you may enjoy...
Featured review
This is an amazing rental and the owners are the nicest people you will ever meet. The home is on the water and one house from the Gulf of Mexico. Sit on your own private dock and watch the Manatees, Dolphins,...
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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Our Cancellation policy is: Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be...
Featured review
This property is about a half hour north of Key West....perfect for relaxing but close enough to go to town and enjoy the party and any boat trips you might want to take. We would consider renting it again....
Distance to beach: 0.8 miles to Simonton Beach
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AboutClassic Old Key West HomeThis home offers a rare combination of location, charm, and character. With a beautiful mix of historic details and modern updates throughout, it’s perfect for couples traveling together or anyone hosting visitors during their stay in paradise.Primary guest...
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PROPERTY NAME: Bella 109 Valencia Drive Tavernier, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Venetian ShoresMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 86DESCRIPTION: Luxurious 4-Bedroom...
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PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachMINIMUM STAY: 90 days, this is a 3 month minimumMILE MARKER: 74.5DETAILS: You will love this charming and cozy Keys Holiday...
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Our wonderful, Oceanside and waterfront home is just two minutes from the Atlantic Ocean and Vaca Cut. No bridges to the Atlantic and super easy to access the Gulf via Vaca Cut.This home is completely remodeled and features brand new furniture throughout. The 55 foot dock is brand new and awaits your...
Featured review
We had a great time escaping the cold weather up north. Accommodations were excellent as were our hosts Jamie and Charlie, they were very responsive to any questions we had and made us feel welcome. We...
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Blue Tranquility will be the perfect destination to get some rest and relaxation for your next Florida Keys vacation. Located directly on the ocean side of South Pine channel, which offers wonderful sunrises and moon rises. Kick back and enjoy the balmy breezes on the serene screened in porch. The pool...
Distance to beach: 4 miles to Founders Park
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Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air...
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Large, very spacious, beautifully appointed 7 BR home with breathtaking ocean views, large dock, pool, 2 jacuzzis, BBQ grill, 4 kayaks, large tiki, two fully equipped kitchens, all new appliances and major upgrades since Irma. Comfortably accommodates multiple families. Very private and secure with property...
Featured review
We loved our stay at Casa Lorelane! We had 18 people and never once felt crowded. The living area on the second floor was amazing. The second kitchen on main floor made it easy to prepare food to enjoy...
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Newly renovated cottage with million dollar oceanfront views.The beautiful in ground private pool will give the serenity you need for a relaxing escape with unobstructed view of the ocean, you can enjoy breathtaking sunsets, watch boats drift by, and listen to the soothing sounds of the waves—all...
Featured review
I stayed in the newest cottage . It was very clean and every essential needed. Mark was thoughtful enough to put bottles of water in the refrigerator for us . I had coffee every morning on the upper Tiki...
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This brand new 5/6 bedroom 4 bath oceanfront home has a private pool and will share dock space, kayaks and the gazebo with Blue Palms Retreat home. There is 1 double and 3 single kayaks. Bring your boat- up to 24’ and your snorkel gear. Relax on one of the porches overlooking The Atlantic Ocean...
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The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is...
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What a great sunset view from this house! Fun in the sun surrounds this spot right on a wide canal with excellent access to fishing either the Gulf or the Atlantic side. Any outdoor enthusiast would be content here as the boating, diving, snorkeling, or kayaking is right out your back door.After a...
Featured review
This house has just about every and anything you could need. Very quiet and nice area. Owners went out of their way to ensure our stay was as stress free as possible! We had a 19’ boat docked at the canal...
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Must See Stunning 3095 Sq. Ft 4/4 SFH on ground level with pool, 45 ft of dockage, outdoor kitchen and access to the ocean by boat.This gorgeous property features an open floor plan with elegant furnishings, state of the art kitchen with Viking appliances and an induction cooktop, quartz countertops,...
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I didn’t know much about Marathon other than it was in the keys. Upon hearing from a family friend that it was the Keys best kept secret we couldn’t resist. The Sunny Daze house was perfect for my family...
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Amazing Waterfront Home with Fabulous Pool and Sunset ViewsWelcome to the Sugarloaf Guest House, the perfect Florida Keys Island Getaway. As you enter the gate to this charming seaside cottage, you will experience its charm and relaxing vibes. A gorgeous new pool with graceful waterfalls make it the...
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Summerland Cottage-Relax At Our Little Piece of Paradise!Host Missy Proctor Phone meeting is required before booking approval. Please email me for my number and any questions you may have :)Come and Enjoy our Cozy Little , Nostalgic Keys Stilt Cottage on Summerland Key! Enjoy Open water views...
Featured review
We are a family of three with a 16-year-old son. We rented on the adjacent Cudjoe Key for the last 15 years. We focus on fishing, snorkeling, and exploring the area by boat. This year, our usual rental...
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Recently built from the ground up. Three bedroom, three bathroom piece of paradise on a saltwater canal with easy access to the ocean. 50’ dock, pool, outdoor kitchen, plenty of parking. Close to super market, hospital, and many amazing restaurant’s. Full kitchen with everything you may need....
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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...
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This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....
Featured review
We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...
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Welcome to Margarita Manor – Your Tropical Escape in the Florida Keys!Set your watch to island time and relax at Margarita Manor, a vibrant waterfront oasis perfectly suited for sun-chasers and boating enthusiasts alike. Located just moments from open Atlantic waters, this breezy retreat offers...
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Tom's Oceanfront PenthouseExperience coastal luxury at Tom's Oceanfront Penthouse, a stunning 3-bedroom, 2-bathroom unit ideally located in a prime spot within the complex. Just steps from the elevator, this expansive 2,000 sq. ft. penthouse offers the ultimate in comfort and convenience,...
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Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and...
Featured review
Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...
Distance to beach: 2 miles to Smarthers Beach and Higgs Beach
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This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and dining...
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Sunshine House on Harris Street, Key West is a Home away from Home. We enjoyed 2 months of comfort and convenience at this home. The home is furnished with tasteful Island Decor. The layout is 3 bdrms...
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Welcome to Turtles Nest! A beautiful 2-bedroom 2 bath condo in the heart of Marathon complete with 40' boat slip and a private boat ramp! 30 steps to the water and heated pool, this 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front...
Distance to beach: 3 miles to Sombrero Beach
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Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s...
Featured review
Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was...
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Coastal Themed Villa Retreat in Paradise Awaits for You! Spacious Large Open Floor Plan on 2nd Floor with large Family Room and 2 Large Bedrooms each on opposite sides of the unit. Large Open Kitchen to Family and Dining Area...Bathrooms are also Coastal Themed. Villa is quiet and peaceful surrounded...
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The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...
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Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...
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RARE SINGLE STORY 2500 sq. ft Canal Front Home with gorgeous POOL! Relax in this spacious and serene space with 3 large bedrooms with 3 en-suite baths, plus additional full bath near pool. Kayaks, paddle boards, ping pong, bicycles and pool table! 8 guests only, 6 adults & 2 children. 28 night minimum...
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From sunrise to sunset you can enjoy the many activities our Florida Keys resort has to offer. Fine restaurants and shopping are just minutes away, along with boating, fishing, snorkeling, diving, Everglades eco-tours, glass bottom boat reef trips, para-sailing, wave runners, and swimming with the dolphins....
Featured review
The incredible view! The kitchen has everything (though we didn't intend to do a lot of cooking!). The unit has a short walk to the pool, snackbar/bar, and the restaurant/bar. There is also a small natural...
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