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4 bedroom/3 bath Canal front home.7 nights minimum. Enjoy coastal breezes in this canal front Villa. Beautifully decorated. 4 Bedrooms/3 Baths. Two King Master Suites with attached baths. One on first floor. Fully stocked Gourmet Kitchen. Dining area seats 10. Flat screen Satellite TV's in each...
Featured review
Very Clean, stocked with the right amenities, great location, very fun time, Would highly recommend for those looking for a central location in the Keys
Key Amenities
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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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Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star property. Tile floors, open and airy kitchen, living and dining area...
Featured review
Not my first time with action keys, always had good result with everyone at this company! Wish they would rework there utilities policy , it’s hard enough to pay rent for a month.
Key Amenities
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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...
Featured review
Everything about this property was amazing. Nice gated community, well maintained and friendly. Our condo was large with enough space for our children to spread out. Pools and hot tubs were the appropriate...
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If you're seeking a respite from the harsh Northern winters or simply craving soulful rejuvenation, our home at the Rock Harbor Club in Key Largo is the perfect sanctuary.Positioned directly on the beachfront, our townhome promises an idyllic setting for your ultimate relaxation. Step outside...
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PROPERTY NAME: Ocean Harbour K31 87851 Old Highway, Islamorada, FloridaLOCATION: Ocean Front CondoMINIMUM STAY: 28 Days, MILE MARKER: 87.8DETAILS: Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. Check out the photos! The kitchen was completely...
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Aaarrrghhhhhhh MATEY! Florida Keys Vacation Rentals – Looking for a perfect sunny get away in the beautiful Florida Keys? Blackbeard’s Bounty is just the place for you and your guests!This tropical oasis is located on Little Torch Key and is only 28 miles from Key West. Situated on a wide...
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The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer.This home is beautifully decorated in island style with attention to even the smallest...
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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...
Distance to beach: 100 feet to our back yard...steps away from the house
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The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerland Key, mile marker 25. The house is an open floor plan with panoramic Atlantic Ocean views and a large wrap-around deck. Two bedrooms (the oceanside bedroom has a king bed and the...
Featured review
Fantastic location, the view from the sunroom is fantastic. Postcard sunrises to start the day! House was very well equipted with everything we needed during our stay, hosts reached out to check on us...
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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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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...
Distance to beach: 0.5 miles to Sombrero Beach
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Exclusive Sombrero Beach vacation retreat is located just up the street from one of the best beaches in the Florida Keys. Sombrero Beach is a large sandy beach that offers something for everyone in the family including playground, volleyball swimming and picnic tables. The beach is also a great place...
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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: 0.5 miles to Simonton Street Beach
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Welcome to the Dancing Rooster, your charming retreat just 2 blocks from Duval Street in the heart of downtown Key West! Nestled within the historic Simonton Cottage enclave, our recently renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience. You’ll be surrounded by...
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Shipyard Pool Closure The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. We expect the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026.Best Deal in Truman Annex – Céad Míle...
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...
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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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PROPERTY NAME: The Salty Pelican 163 Paradise Way, Islamorada, FL 33036LOCATION: Ocean sideMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 87The Salty Pelican invites you to experience laid-back island living in the heart of Islamorada,...
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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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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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 moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged...
Featured review
We had an amazing stay at this Airbnb in Islamorada, Florida! The property had everything we needed and felt comfortable from the moment we arrived.One of the biggest highlights for us was the boat...
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Plentiful. Key Colony Beach 4 bedroom with 37 Ft Dock, Pool Club. Sleeps 10 Spacious, 2200 sq ft duplex home on a wide canal with dock in beautiful Key Colony Beach.Includes free use of nearby, ocean-front beach club with a huge, temp-controlled pool and Hot Tub!!Lower Level - 1 bedroom, 1 bathroom...
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This charming 2-bedroom, 2-bath rental home is perfect for your tropical getaway! With a minimum stay of 28 days, it accommodates up to 6 adults and 1 child, making it ideal for families or groups. The master bedroom features a king-size bed, while the guest bedroom offers a queen-size bed. Additional...
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, one...
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 Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, friendly lane with two parking spaces right in the middle of all the action. Four bedrooms (one king and three queens) - each with their own attached bathroom - plus a half bath on the...
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Located directly on the runway at Summerland Key Cove Airport, this extraordinary 2018 custom-built hangar home delivers the ultimate fusion of aviation lifestyle and refined island luxury in the heart of the Florida Keys.Designed for discerning pilots and luxury tentants alike, this home was engineered...
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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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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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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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Beautiful canal waterfront stilt home in Key Largo. Home features concrete sea wall and boat lift. Easy access to the Gulf of Mexico and within minutes of the Atlantic Ocean. Amazing fishing and diving spots. The home is completely updated with smart TVs in each room, indoor laundry room, and a fully...
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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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PROPERTY NAME: Casa Lisbon 125 Lisbon Court, Islamorada, FloridaLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Port AntiguaMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 74.5 DETAILS: Casa Lisbon offers a...
Distance to beach: 300 feet to Southernmost Beach
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This beautiful one bedroom, one bath condo is located in the Historic District, Old Town Key West . The condo is approximately 50 feet to Duval Street. It sleeps up to 4 people, one bedroom with a queen bed, a sleeper sofa in the living room which sleeps 2. One bathroom with a stand up shower and...
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Are you looking for a home on Big Pine Key with open water views? Look no further! This two-bedroom, two-bathroom home has it all. No shortage of outdoor living space here! There are TWO upper decks with equally great views, one is screened in, and both are nicely furnished. The lower level has a hot...
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Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...
Featured review
Love Beacon Reef and the unit was very comfortable and well equipped. Very close to the pool and the staircase from the balcony was convenient
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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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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
Loved everything. We enjoyed the pool, the long pier, and the ocean breeze. Everyday was relaxing. Many great restaurants close by.
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Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and...
Featured review
We stayed at this location in April-May 2026. It was amazing. My parents stayed with my husband and I and our 10 year old son. The unit was immaculate. It was clean, beautiful and fully equipped for our...
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Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch...
Featured review
We enjoyed a family vacation for one week at this "villa". The view was spectacular and the interior spacious. There were plenty of spaces for all of us to sit and visit with each other. The pool was fun...
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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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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
House was perfect for me--quiet and peaceful. Never rented a house with a pool before, but this was wonderful. No mosquitos. Boat dockage was ideal. The fish cleaning table, which I used a lot, needs a...
Distance to beach: 0.4 miles to Fort Zachary
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Escape the winter and settle into this beautifully renovated 2-bedroom, 1-bath condo in the heart of Old Town Key West — perfect for snowbirds and monthly renters seeking the ideal balance of tranquility and convenience. Located in the prestigious gated community of Truman Annex at the Shipyard...
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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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Relax & recharge at our quiescent condo with stunning views of the blue-green colors of the Atlantic all nestled on 60 secluded acres. Seas the day – or just relax – you’re on island time!The Space This unit is located in building 3 which is a desirable building. Featuring...
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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...
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
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...
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Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends...
Featured review
Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is...
Distance to beach: 8 miles to Founders Park Beach
Key Amenities
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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...
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