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Welcome to the home with one of the best sunset views on Big Pine Key! This is a great location, with awesome views, and super quick boating access to both the Gulf and the Ocean. This three bedroom, three bathroom home is setup perfectly for the avid fisherman, boater, paddleboarder, or just the relaxed...
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“Endless Paradise” is truly a Cudjoe Gardens gem! This ground level (no stairs here!) vacation rental home is walk in and relax ready! Located in the highly desired Cudjoe Gardens neighborhood known for its great boating access, ground level prestigious builds, local marina and don’t...
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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...
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Florida Keys Vacation Rentals – Start your vacation in the Keys off right at Blackbeard’s Escape! This unique home has it all. Main living area on first floors is a 2-bedroom 1 bathroom home with gourmet kitchen, lovely finishes and details plus comfy king size beds. Cooling is great with...
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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...
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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.
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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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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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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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Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key.A cute tropical them from the outside in, you know you are in the Florida Keys! The exterior boasts an immaculately kept grounds with ample storage for your gear,...
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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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You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops.The...
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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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You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and...
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Keys Life Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around...
Featured review
Enjoyed our stay at Keys Life. The home was beautiful. The weather was quite windy so we weren’t able to get out as much as we wanted in our boat but we were able to get some nice lobster! It was nice...
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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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Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay!This 3-story custom home has 3-bedrooms and 3 bathrooms, and has upscale yet comfortable living on one of the best islands in the lower keys for open water location for boating, fishing, diving or snorkeling....
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INGROUND HEATED AND CHILLED POOL TO COME IN NOVEMBER!! Daydreamin’ blue in the super-desirable Summerland Cove neighborhood! There is plenty of room for family and friends here, with four bedrooms and a huge open concept kitchen and living room, you won’t ever feel crowded. Additionally, a...
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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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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...
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Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...
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Welcome to El Paraiso, a true Cudjoe Key gem at an affordable price. This three bedroom, three bath home is nicely updated throughout! Located on Lafitte Drive, right behind the famous Square Grouper restaurant and only 20 minutes from Key West. Don’t forget to bring your boat, there is plenty of...
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Welcome to Paradise Palm, a home away from home that encourages outdoor fun and relaxation with its unforgettable exterior amenities! Nestled in a quiet neighborhood, this beautifully furnished home offers a perfect blend of comfort and luxury.Step outside and be greeted by an excellent space that...
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Welcome to “Summerland by the Sea,” an expansive waterfront property located on the very desirable Summerland Key and pet friendly! Combine the amazing waterfront views with the excellent access to both the Atlantic and the Gulf, it just doesn’t get any better than this!This home...
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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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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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This super cozy, comfortable 2-bedroom, 2-bath vacation rental is located in the heart of Cudjoe Key, just minutes from the open ocean. Perfect for fishing, snorkeling, and diving enthusiasts, the home boasts easy access to some of the best spots in the Florida Keys.Relax and unwind in style after...
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This unique home is situated on a quiet street, with a desirable corner canal location in Port Pine Heights, Big Pine Key. Bringing your boat along? No problem, plenty of dock space here! And quick and easy access to Pine Channel for excellent boating, fishing, diving and snorkeling!The exterior has...
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Looking for the perfect getaway for your Florida Keys vacation? Look no further! Tropical Oasis is just the home for you and your guests with only 23 miles to Key West; not that you’ll ever want to leave the beautiful views of the mangroves and sea-life!Tropical Oasis is a two bedroom, two bath...
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Latitude Adjustment equals attitude adjustment! Location Location Location! This vacation rental home is located in the super desirable Summerland Cove neighborhood, with easy quick open water access!Whether you are coming for the weather, the boating, the diving or just to relax, this home has it...
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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 extraordinary island castle will make you feel like the royal family! With four bedrooms and five bathrooms you will not have to share your space! Start your day boating, fishing or kayaking and then return for a cool dip in the pool! Relax on the expansive screened in porch with a drinks and appetizers...
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Welcome to Yellowstone by the Sea! A spacious, two bedroom, two bathroom, vacation rental home located on Big Pine Key with excellent, quick, open water access. This home truly has the “Keys” vibe inside and out. Plenty of space to relax and chill canal side or poolside! The open concept kitchen,...
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The welcoming views at Coral Cove are waiting for you! This brand new two-bedroom, two-bathroom home is located on the open water and canal on Saddlebunch Key, just a stone’s throw from the famous “Baby’s Coffee.” You’re at Milemarker 15 and Key West is just minutes away!This...
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A Little Torch, Jolly Roger Estates unique find! Two separate living spaces for the price of one! Located in one of the most desirable neighborhoods in the Lower Florida Keys, this canal front home is truly a vacation rental you will remember.The Cat house, so called because of the original cathead...
Featured review
Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key...
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Florida Keys Vacation Rentals – Nestled on a pristine canal-front lot, situated in Little Torch Key, this well-appointed home offers all the amenities you will need to enjoy the casual lifestyle of the Lower Keys. The lovely back yard area has a gas BBQ grill, a dining table with seating for six,...
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Florida Keys Vacation Rentals – This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining...
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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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Welcome to Barefoot Retreat, where you will feel as though you are on your own private island! As you drive through the remote, lush tropical island road to access the estate, drive slow as you might be greeted by the quite friendly protected Key Deer, roaming free about the property.As you approach...
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Welcome to the Snow Grouper, a classic and comfortable vacation rental home in the much sought after Summerland Cove on Summerland Key.This home is a two-bedroom, two-bathroom up, and a one bedroom full apartment downstairs, and is completely remodeled, with a layout that is welcoming, from the open...
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Welcome to “Casa Solimar,” house of the sun and sea! When you arrive at this home you will see that the name suits it…situated canal front and just a few homes in from open water, with a heated pool and spa! The lower-level boasts an updated additional living area for family and friends,...
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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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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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Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing.The shady screened porch overlooks the crystal...
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Florida Keys Vacation Rentals – “WOW!” is what you will say when you walk through the door of this Little Torch Key home. With cathedral ceilings and a large family and dining area, your whole family will be able to stretch out and relax.The updated kitchen looks out to the canal...
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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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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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Start your vacation in the Keys off right at Blackbeard’s Escape! This unique home has it all. Main living area on first floors is a 2-bedroom 1 bathroom home with gourmet kitchen, lovely finishes and details plus comfy king size beds. Cooling is great with mini ac splits and large flat screen tv’s...
Featured review
Our family throughly enjoyed our stay at this house. It was very clean and there was plenty of room. It was perfect for the fishing families. Plenty of dock space, a bait freezer, and an ice machine. We...
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The name says it all, find your dream vacation home at Million Dollar View! Located on Big Pine Key, this perfectly placed piece of paradise sits on a convenient corner lot, providing ample space for boats, and some of the fastest access to water you can get anywhere in the Keys! When you aren’t...
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Meet your perfect vacation getaway, Maracaibo Manor! Located on Little Torch Key in the highly desirable Jolly Roger Estates neighborhood, with excellent deep water access for boating, diving, fishing and snorkeling at the famous Looe Key Reef.This roomy home has two bedrooms and two bathrooms upstairs,...
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Welcome to Bow Channel Manor and step back in time to Old Florida! You’ll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key.The grounds are like a playground. There is a full-size heated pool...
