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Sea Magic on Marlin – Panoramic Open Water Views & Spacious5-bedroom HouseYour Sugarloaf Key adventure begins at this beautifully located waterfront home. Panoramic water views and access allows for boating, swimming, kayaking, snorkeling, and fishing and this 5-bedroom house welcomes...
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Enjoy our charming top floor condo at Ocean Pointe Suites with lush mangrove and peek a boo ocean views. Ideal for couples, families, solo & budget travelers, Key West Road Trippers, Snowbirds, Sea-foodies, Divers, Snorkelers & Anglers.You and your guests will be close to everything when...
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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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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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A comfortable well priced home away from home. This charming 2-bedroom, 2-bathroom cottage offers a spacious, living/dining area with a fully stocked kitchen only steps away from the shaded patio with a water view and firepit. NEW to the Property - Heated Swim Spa!Experience the coastal charm and...
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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: 5 miles to Bahia Honda State Park
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Welcome to your very own “Island Escape”! This beautiful home is located in one of Big Pine Key’s most favorable boating neighborhoods with quick ocean or gulf access for most any size boat. It’s only a few lots in from open water! The large 75’ concrete dock offers plenty...
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Welcome to Oceanview Oasis, a most spectacular open water home on Summerland Key. This is a completely remodeled, state of the art, waterfront retreat with new oceanside pool, adjacent spa and screened porches on two levels for outstanding views at every turn.Interior living space offers a split floor...
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Indulge in the peaceful scenery at our impeccably designed oceanfront property, recently renovated, and situated at Ocean Pointe Suites.Upon your arrival you will be greeted by the turquoise colors of the Atlantic Ocean and coastal décor in our two bedroom, two bathroom condo. The comforting...
Distance to beach: 3 miles to Sombrero beach
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If you are looking for a tropical Keyz experience, you have arrived in paradise at this three bedroom two bathroom home on a direct ocean access canal which has all the comforts of home and more. **This is a 3 bedroom 2 full bathroom rental** There is no ground floor apartment or access. This is owners...
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Welcome to Anglers Paradise, your waterfront retreat in Marathon, FL! Nestled on the tranquil Atlantic side, this cozy condo offers everything you need for a perfect Florida Keys getaway.BYOB: (Bring Your Own Boat) Vessel & Trailer Registration must be up to date for consideration. Documents...
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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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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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Welcome to Keezy Does It at Anglers Reef in Islamorada!A charming, oceanfront gated community in the heart of Islamorada, the sport-fishing capital of the world!Delightful Key West-style architecture entices you through the entrance security gates into this enchanting enclave of 52 private...
Distance to beach: 0.1 miles to At Kawama Yacht Club
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Enjoy Key Largo - A Year Round Vacation Paradise *** Short Term Rentals Available**** * * NO PETS * * *NO PETS * * *NO PETS * * *. - the Associate does not permit renter's pets!!!* * * SPECIALS LISTED HERE WHEN AVAILABLE * * * RATE REDUCED - March 7 - 11 (4 nights) Inquire...
Featured review
We have stayed in Kawama yacht club several times over the years. This is our second time in this particular condo. Everything you could possible need is in this condo. Another huge benefit is if there...
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Please be advised that the building elevators will be out of service for modernization from April 27, 2026 through, June 19, 2026. During this time the elevators will not be functional — all guests and visitors must use the stairs.Beautiful top floor ocean front 2 bedroom 2 bath condo at La...
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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Beau Soleil is located in the most sought after neighborhood in the Lower Florida Keys, Summerland Cove, on Summerland Key. A gorgeous gem, tucked away in privacy with tropical plants and fruit trees everywhere you turn!This home is situated on a great boating canal with plenty of dockspace for your...
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Beautiful Ocean Beach and Pool view from the deck. Relax in paradise where everything is steps away! Suntan on the white sand beach complete with chairs, tiki and palm trees! Spectacular sun sets!Condo is townhouse style with stairs to bedrooms. Master bedroom has king bed with full private...
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About this spaceWelcome to Angler’s Reef Resort Villas & Marina - a stunning Islamorada vacation destination. This two bedroom, two and a half bath conch house overlooks the resort style swimming pool and is available for weekly and monthly vacation rentals. Our home has ocean views, 2 spacious...
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Multi-million dollar views and the peace and quiet you expect in the Keys. This completely renovated condo has direct views of Florida Bay throughout, and the property includes white sandy beaches, a clubhouse with a new gym, sauna, and firepit. The property also boasts a swimming pool, bocce, basketball,...
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
We spent 10 days at Joe's condo. Everything was perfect , spacious , clean & very comfortable. The view of the bay was gorgeous. There were manatee that came up to the seawall as well as parrot fish , angel...
Distance to beach: 0.3 miles to Sunset Park
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This beautiful, modern and stylish home is perfect for families and group vacations. It features high quality and modern furniture and beds, a fully equipped kitchen, high-speed wireless internet and a private, heated pool.This is the lower half and if you book a reservation, there WILL NOT be people...
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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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This pet-friendly home completed in 2012 has 5 rooms, 3 king-size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep the...
Featured review
SIX STARS * * * * * *This is a wonderful home with channel access right behind the house. It's perfect for the whole family, very spacious. The owners are very accommodating, making sure everything...
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Relax amongst the tropical sights and sounds in this charming oceanfront condo located in Ocean Pointe Suites. Ideal for Couples, Solo & Budget Travelers, Key West Road Trippers, Snowbirds, Sea-foodies, Divers, Snorkelers and AnglersSEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME! The...
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Welcome to Your Private Oceanfront Oasis in Marathon, Florida!Discover an unparalleled retreat in the heart of the Florida Keys where every day begins with breathtaking sunrises over turquoise waters. This charming oceanfront cottage effortlessly blends a relaxed beach vibe with upscale comforts,...
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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: 8 miles to Founders Park Beach
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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 near the heart of Key Largo and has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all...
Featured review
From the moment we opened the door, the view was absolutely captivating - better than the photos!The condo is beautifully appointed with a cool beachy vibe and everything you'd need to make your stay...
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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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.
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PROPERTY NAME: The Bungalow House 32 Park Rd Islamorada, FloridaLocation: Bayside Very close to the Publix Shopping CenterMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedMile Marker : 82Details: This home is absolutely beautiful with your own pool and...
Distance to beach: 10 miles to Bahia Honda, Key West
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Wonderful, pet-friendly and beautifully decorated 3/2 home on the water that's perfect for a vacation or simply relaxation. It's located on beautiful Cudjoe Gardens with direct ocean access. There's a marina within walking or rowing distance. Check out the nearby Marvin Key video.Summary: •...
Featured review
My husband and myself along with another couple rented this property for 28 days in September 2022. The home is clean, very comfortable and nice. There is a canal at the house which we used to dock 2 boats...
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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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Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...
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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...
Distance to beach: 2 miles to Sombrero Beach
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Waterfront Keys home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, half-duplex home with private pool, dock with great amenities - perfect for three couples or a family. Great location that's walk-able to the 7-Mile bridge and some of Marathon's best restaurants and bars. Incredible...
Featured review
We absolutely love staying at this property! We rented a boat for the week this visit and it was so nice to walk past our private pool and jump in our boat or fish right off the dock. Manatees swim by almost...
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Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired apartment, over looking the marina located in the 5th building, offers two bedrooms and two bathrooms, Free Parking, High-Speed WiFi, Fully equipped kitchen- Washer and dryer. Self...
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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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Come vacation at our 2 Bedroom, 2 Bathroom, canal front property located on the Island of Key Colony Beach in the Middle Keys. Our house sleeps 4 people including kids and has dockage right our back for up to a 40-foot boat. You can fish right off our dock on the Island's largest, deepest, most...
Featured review
We have been coming to Steve Barnett's homes (now one of his daughters has the duplex) for many years. It's the only place or places we stay. Would highly recommend both. Steve's canal front home is...
Distance to beach: 1 miles to cocoplum
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Are you ready to Seas the Day? 30 steps to the water and heated pool, this completely renovated 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front community - steps from heated (and chilled) saltwater pool (easier on eyes, skin and...
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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Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 GuestsWelcome to Innis-free, our little slice of paradise in Key West—where you're greeted with Céad Míle Fáilte, an Irish expression meaning “a...
Featured review
We really enjoyed the unit at Shipyard Condos. Very clean and well equipped. Walking distance to local restaurants and very convenient with a dedicated parking place. Pool was nice too. There were only...
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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Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As...
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Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys.FLORIDA KEYS VACATION RENTALS! This stylish home is outfitted in Florida tropical style with cool and...
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We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom...
Featured review
We had a wonderful month in Islamorada at this outstanding waterfront condo with pool and sauna, dock etc. The views were gorgeous from the 3 decks in this corner unit. The area is exciting and near both...
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,...
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Welcome to Calypso Corner! This spacious, tropical home that sleeps 6+, sits on a large corner canal lot and has a huge dock that can accomodate most size boats. Located in sought after Jolly Rogers Estates, the canals are large, flow through and swimmable and open water is only a few minutes away with...
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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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