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Welcome to Flamingo Island Paradise!Step into this updated spacious home and enjoy! Tasteful, fresh decor matched perfectly for this relaxation paradise. 2 Master suites with ensuite bathrooms and comfy King Beds. There is a pullout twin in the living area for an extra guest. Updated well stocked ...
Featured review
This is a great location for two couples exploring what the Florida Keys has to offer. We did not have a boat or plan to fish so the residence could’ve accommodated both of those things. We did use the ...
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THE MAD MAHI is a beautiful water-front 1 bedroom / 1 bathroom condo with a full kitchen, private balcony, pool, Tiki Bar, restaurant, boat ramp, trailer parking and boat slips on site! It is located in the heart of Marathon close to everything. Sombrero Beach, Docksides Bar & Grill, Publix, Walgreens ...
Distance to beach: 7 miles to Sombrero
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Great news, we just completed construction of a brand new 60FT dock. We have a kayak launch and plenty of room for your boat.Our indoor upgrades included getting a Tempur Pedic king-size adjustable bed for the master bedroom (raise the head or feet). All the TVs are now 4K smart TVs, which we mounted. ...
Featured review
This house has the latest and greatest of everything. It's beautifully decorated and located on the best part of the island. Over looking a heated pool, it's steps away from an elevated observation deck ...
Distance to beach: 1 miles to Sombrero Beach
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Embark on an idyllic getaway to our spacious 4-bedroom, 3-bathroom vacation villa nestled in Marathon, the heart of the Florida Keys. Escape to Stay Anchored, where tranquility meets luxury. Boasting a prime location on a spacious canal, our retreat features a private heated and chilled pool, inviting ...
Featured review
Stay anchored at Sombrero was an amazing property....The location was perfect for our group. The house is very comfortable and welcoming. The property owners are exceptional responding promptly to any ...
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Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and ...
Featured review
The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!
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Stunning rooftop views from this gulf side Tuscan style Villa3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougainvillea Clients overlooking The Gulf of Mexico.There is Great Fishing at this location! You can bring your boat in for ...
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki ...
Featured review
We had a fabulous stay in your property. We really appreciated all of your amenities. We love to cook some of our meals in and you had a great selection of pots and pans and dinnerware. We also like ...
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Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation.Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~Tiki Hut, ...
Featured review
From beginning to end it was a pleasure working with Liz to secure the week of family fun! The estate was everything that we needed it to be with plenty of room for our children and grand children. The ...
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!This beautiful 4 bedroom, 3 bath home is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! Private pool with outdoor tv on the patio, private ...
Featured review
Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.
Distance to beach: 100 yards to Sombrero Beach
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Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home ...
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Welcome to our waterfront family home located in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and receive ...
Featured review
The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs. ...
Distance to beach: 2 miles to Sombrero Beach
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Our waterfront, single-family home, affectionately named “Turtle Cove”, offers 3 bedrooms, 2 baths, and an 80 ft seawall with quick ocean access! This tastefully furnished Keys home is located on a quiet side street in a residential neighborhood on the Atlantic side of the Island, just 5 houses ...
Featured review
we stayed at turtle cove with friends and family. it was Amazing so relaxing . The house was great , roomy , great location . the pool was perfect . we enjoyed the 2 separate levels of living . we rented ...
Distance to beach: 4 miles to Sombrero Beach
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New construction! This spacious and tropically decorated property includes 4 KING bedrooms, each with private ensuite bathrooms. There is an additional half bath for guest use, as well as commercial washer and dryer. State of the art kitchen with quartz counter tops and well appointed living area including ...
Featured review
We spent a week at this lovely home in Marathon Key, escaping our winter wonderland in Michigan. The 4 bedrooms and baths were ideal for our group of seven. The kitchen is well stocked, the deck has plenty ...
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and ...
Distance to beach: 1 miles to Sombrerro Beach
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Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring, ...
Featured review
10 ️ Rating! I called Florida Rentals. I Booked. Counted Down the days until our Christmas vacation began. We were able to take homemade cookies to the USCG base on Christmas Day. We were able to see ...
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Oceanside Condo, steps to the ocean! Located in a gated fishing village in Marathon. Huge heated pool, clubhouse and gas grills, fish cleaning stations, open grounds along the waterfront edge, perfect for corn hole, table tennis and other games available on the property. WIFI provided.This gated oceanfront ...
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Welcome to your spacious, five-bedroom waterfront pool home in Marathon, just steps from Sombrero Beach! Enjoy multiple entertaining areas inside and out, with a screened-in patio and sparkling pool (pool heat available for an extra fee). The open-concept interior features cathedral ceilings, a modern ...
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground ...
Distance to beach: 0.1 miles to Sombrero Beach
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Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest ...
Featured review
The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing. ...
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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Inquire for monthly discounts.The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish ...
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This 3 bedroom, 2.5 bath single-family modern home is great for entertaining! Enjoy the outdoor area with a pool and a separate hot tub or catch a game of pool on the main floor. This home is located on the 63rd Street canal and being ocean-side, it's just a quick trip out to sea where you'll ...
Featured review
Spent Thanksgiving week at The Keys Retreat. Perfect location, house was very clean and kitchen stocked with everything you need. Really enjoyed the outside area in the pool and jacuzzi.
Distance to beach: 0.1 miles to On site
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BEST SUNSETS in the Keys, Key Colony Point unit #15, Ocean Beach Front, 2 bedroom, 2 bath ensuite, newly remodeled Condo with new furniture.COMPLEX: KEY COLONY POINT UNIT #15 Perfect get away for a week or a month.BEACH is 30 feet from our balcony. 150 feet to pool with hot tub. Great fishing ...
Featured review
Absolutely the best view and pool in Key Colony. Spacious and well appointed condo. Would repeat #15 Very quiet and relaxing without crowds and annoying children!
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Direct oceanfront condo with stunning views of the Atlantic. Large heated pool, tennis, hi speed wifi. Stroll along the long span of beach or relax at the oceanfront pool. Or just sit on your private balcony and watch the world go by. Large open living area, master bedroom with King size bed, the guest ...
Featured review
The condo well appointed with everything you would need for your stay. The pool beautiful and warm, unfortunately the railing on the stairs of the shallow end make it difficult for an adult to get in or ...
Distance to beach: 1 miles to Sunset Park
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Family-friendly Waterfront Oasis w Heated Lazy River Pool and 70' Dock Summary: Bring the family to the Florida Keys vacation of your dreams! Located in family-centered Marathon while still located in the middle Keys with the best access to the whole of the Keys for exploration. Enjoy ...
Featured review
We could not have stayed at a better place in Marathon. The owners Roger & Amy are great hosts. We hardly saw them but it was nice knowing if we needed something they were close by. The view from the ...
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Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional ...
Featured review
I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would ...
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise ...
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Ocean OasisEscape to this newly built, stunning 4-bedroom, 3-bathroom vacation home on stilt nestled in the heart of Marathon, FL. Perfectly situated in Coco Plum and boasting a private pool and dock, this retreat offers everything you need for an unforgettable getaway in the Florida Keys.Property ...
Featured review
We stayed for over a week with our kids and 3 grandkids. Kids fished and swam every day. House was perfect, clean and well stocked. Robin (manager) was over the top good. Handled any question promptly. ...
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Mar Azul is a High-end Oceanfront Residence overlooking the tranquil 'Bonefish Flats' of Marathon. Enjoy a Private, Secluded 3-Story Home with Spectacular Views of the Atlantic Ocean! Densely surrounded by Nature, the Property includes a Private In-Ground Pool Deck featuring an Outdoor Gazebo ...
Featured review
Great house is equipped with everything you could want or need! Beautiful property and very peaceful. We had a fantastic vacation. Our dog had fun too!! Lisa is great. We plan on visiting again!
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), ...
Featured review
Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private ...
Featured review
Meredith and Pineapple Properties were very accommodating, and answered all of our questions. The home, the pool, and the hot tub are all in great working shape, well-maintained, and clean. The property ...
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Villa FranchellaEscape to paradise and experience the epitome of luxury living in this new breathtaking 4-bedroom, 3-bathroom waterfront home in Marathon, FL. Located just minutes from the Gulf of Mexico with easy access from the 45' of available dockage, this newly renovated sanctuary offers ...
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We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with hidden amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good ...
Distance to beach: 4 miles to Sombrero Beach
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Come stay with us! Why?68 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation rental is you won't ...
Featured review
Matt was great to deal with. Villa is beautiful. The yellowtail was definitely set up better than the rest of the villa. Matt has it decorated nice and laid out well. There were 6 of us and we had great ...
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Paraíso Del MarIntroducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This brand-new build epitomizes elegance and sophistication, offering an unparalleled experience for those seeking the epitome of luxury in the Florida Keys.Set amidst lush tropical ...
Distance to beach: 3 miles to Sombrero Beach
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Want to check in on a Tuesday and leave on Tuesday? We can be flexible with your check in day! Still 7 night minimum required.This spacious 3-bedroom, 2-bathroom single-family vacation home, that we lovingly call the SEAHORSE, is great for entertaining! The open living and kitchen/dining area allow ...
Distance to beach: 3 miles to Sombrero Beach
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4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area w/ Full Kitchen, Yard Games, Bikes, Kayaks, Paddleboards!Casa PlayaWelcome to Casa Playa, a luxurious 4-bedroom, 4.5-bathroom home in Marathon, Florida. Nestled behind gates in a 4-home enclave, this custom-designed retreat offers an element ...
Featured review
We had an amazing stay at this property from the moment we arrived, we were impressed with how immaculately clean and upscale the house was. The decor was beautiful, and everything felt fresh and well-maintained.The ...
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We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with ...
Featured review
Simply Put ... GREAT House (attention to detail -unbelievable) GREAT Hosts !!! GREAT Week !!!Thanks you Lynn and Freida and Seth !!!!!
Distance to beach: 3 miles to Sombrero
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Manatee Cove-4BR/2BA, Pool/Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools in one? Swim right up to the Tiki and enjoy the ...
Featured review
My family and I had a wonderful week here. The owner and property manager were both a pleasure to work with. Our favorite amenity was the pool and hot tub. We had plenty of space and all of the beds were ...
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WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero ...
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Casa Feliz~ Experience, enjoy, relax, and rejuvenate in luxury accommodations on the Atlantic Ocean.~ Secluded sophistication can be your vacation destination.Welcome to Casa Feliz! We are located on the quiet Grassy Key in the middle of the Florida Keys.Concierge Level Luxury vacation ...
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Seaside SerenityWelcome to your exclusive luxury retreat in Marathon, Florida. Seaside Serenity is a brand-new, 4-bedroom 4.5-bathroom, private pool home where paradise meets perfection. With 35' of dockage and nestled in close proximity to the Atlantic Ocean, Gulf of Mexico, and Coco Plum Beach, ...
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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Gulf side Gem, 45 ft. Dock, pool , hot tub and moreSpacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the property complete with a fish cleaning station and private pool and brand new hot tub. The Open Concept Living and Kitchen Area ...
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Newly Remodeled 1 Bedroom 1 Bathroom unit, Marina, Pool, Paddle Boats, Kayaks, Tennis Courts, Bicycles. Fun and Sun. Great amenities, close to everything. Boat slips available on first come basis with fee.Outdoor bar b q grills, great Sunsets from the Dock. Fish from the Dock.
Featured review
Neat, clean and very comfortable condo for the two of us. The pool, gazebo, sheltered deck and marina provided a variety of areas to lounge, swim and read during the wonderful 80 degree weather. Plenty ...
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"Wow beyond wow! This place had everything we needed and more. We like to rent a house where we can spend most of our time there enjoying family time. The pool and all the games with the game room and infinity table and the dining turned ping pong was amazing. Eric was very responsive..." - ...
Featured review
The place In Marathon was great !!! It had everything you needed pool the canal to watch the manatee go by close proximity to everything !! The only complaint I would have is TVs in 2 of the 3 bedrooms ...
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VACA-22-238 BRAND NEW BUILD! 3- bedrooms with king beds and full size bathrooms, and 1/2 bath for guests. Large common area living room and open kitchen. Located on canal three houses from the ocean, with great open water views. Pool with sitting area under the house. Our home offers a 60' ...
Featured review
We have been going down to the Keys for years in August. Happened to find Sandy Flats two years ago and loved it. House is beautifully redone and owners are super friendly and very responsive. Loved that ...
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Welcome to our private stand-alone oceanfront home in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and ...
Featured review
In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for ...
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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 came in by boat and had a wonderful stay in this home. Rooms are large and plenty of space to move around. Sunrises are beautiful. Outside freezer for fish and bait was a great asset. Nice area to take ...
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Welcome to “Take it Keysie” your tropical/waterfront retreat in Marathon, Florida!Located in the heart of the Florida Keys, Take it Keysie, offers the perfect blend of luxury, comfort, and adventure for your vacation getaway. Our waterfront property with quick ocean access offers 3 bedrooms ...
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