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The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach...
Featured review
Our stay in Islamorada at Jerry and Lisa's was nothing short of magical. The private beach was a slice of paradise, with palm trees perfectly placed to provide just the right amount of shade. The hammock...
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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 a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles)....
Featured review
We enjoyed our stay. The house was clean and had all those things (towels, beach toys, pool, kitchen essentials) that we were hoping for with our stay in Marathon. The location is great- walking/biking...
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....
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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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Open concept meets modern elegance in this stunning canal-front pool home located on sought after Coco Plum in the heart of the Florida Keys. No detail has been spared, from its spacious design to its functionality and huge outdoor living space, this home is sure to be your dream vacation location! Dedicated...
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Distance to beach: 2 miles to Anne's Beach
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House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large...
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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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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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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 dock (can accommodate up to a 30' boat), fish cleaning station, private pool, hot tub, and...
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...
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 dockage 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 from...
Featured review
Turtle Cove is our favorite place in the Keys. The prime mid -Keys location is perfect for exploring. There is easy access to a variety of restaurants and attractions. The best being the "blue"; blue water...
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Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. Just under an acre boasting a sandy beach w/pretty palms, large custom pool, & deep water dockage w/quick access to ocean, gulf & back country. The open Great Room boasts...
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Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24'...
Featured review
The location was exactly what I had hoped. It was secluded, but close to everything. The water views were worth every penny!
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Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming...
Featured review
This 4 bedroom, 2 bath is more than a house, it feels like home! From the fully stocked kitchen to the various board games available, this house will keep you busy. You can also rest here as the nights...
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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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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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Welcome to San Remo Retreat, a very unique property located in the highly desirable Doctor’s Arm neighborhood on Big Pine Key. Bring your boat, plenty of dock space here! The fish cleaning table will hold your biggest catch of the day!You will feel right at home in this very nicely decorated,...
Distance to beach: 1 miles to Sunset Park
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Family-friendly Waterfront Oasis with Private Heated Lazy River Pool and 70' Dock Summary: Welcome to Your Dream Florida Keys Getaway! Bring the family to experience the ultimate Florida Keys vacation! Nestled in family-friendly Marathon—right in the heart of the Keys—our...
Featured review
Place was clean and open and had all the stuff needed for a great time. Location and price were great too!
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Escape to paradise at our stunning 3-bedroom, 2-bathroom pool home, perfectly situated to offer breathtaking open Gulf views. This inviting retreat is designed for relaxation and enjoyment, making it the ideal getaway for families or friends seeking the ultimate Florida Keys experience.Highlights:Breathtaking...
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A fisherman's delight! This perfectly located 2 bedroom house with a large loft is a perfect place to bring your family or friends for a great Keys experience. It has a 40' dock with access just yards away from the Atlantic ocean and the 7 mile bridge. The property has a large swim spa, ice...
Featured review
Great location to visit both upper and lower keys. Well stocked kitchen and we enjoyed the large deck and swim spa.
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Welcome to Oasis4rent!Escape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.The PropertyMain...
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The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is...
Featured review
My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The...
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Looking to Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset...
Featured review
We loved our time at Key West Sanctuary! The perfect location to bike to the sights and sounds of Key West; close to one-way roads with a bike lane going to/from Duval. The beautiful and peaceful surroundings...
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This Condo comes with tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.
Featured review
Spacious 2 bedroom condo with everything you need. Beautiful view, well equipped kitchen. Comfortable furniture. Well maintained grounds and great pool. You're able to buy fresh lobster/ seafood right off...
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
This was our first time yo Key West, FL. My husband, daughter, and I had a wonderful time. Kraken’s Cove is beautiful with all the amenities and lots of extras too. We went to downtown Key West parts...
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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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Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home.Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront...
Distance to beach: 4 miles to Sombrero Beach
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Come stay with us! Why?71 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!! That's right ALL OF THEM!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation...
Featured review
Excellent location, clean, great accommodations. Easy check in/out. We all enjoyed the view and the pool and sandy area. We did not get time to partake of the hot tub and other amenities but definitely...
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Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock...
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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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Oceanfront Islamorada Townhome with Private Dock, Pool & Sunrise ViewsWake up to panoramic ocean sunrises in Islamorada. This 3-bedroom, 3-bath oceanfront luxury townhome features a private dock, sandy entry for kayaks, and a resort-style pool just steps from your door.Your Keys EscapeSet...
Featured review
We had a great time at peaceful palms. The townhouse was very comfortable and well stocked. Jamie and Charlie were great hosts, very responsive to anything we needed. We had our boat with us and spent most...
Distance to beach: 1 miles to In the Key Colony Beach walking distance
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Hey there, fishing enthusiasts and families!Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot.Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and...
Featured review
Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant....
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Welcome to your remodeled 2 - bedroom, 2 - bathroom vacation rental that has everything you need! The Master bedroom features a comfortable king size bed with a private bathroom that has a walk-in shower. The second bedroom has 2 twin beds and a connecting bathroom. The kitchen boasts beautiful granite...
Featured review
Our trip was wonderful! The condo was clean and nicely decorated. We had plenty of room and the view was priceless!
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Welcome to the cutest little Conch Cottage in the Florida Keys! Located in the Seaside Resort Community, only ten minutes to Key West! You won’t find a more affordable and comfortable location than this! The resort has not one, but two large pools, one that overlooks the open water! Other amenities...
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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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Come live the Salt Life at Salty Retreat! Stay at this luxury top of the Line tropical style home on Summerland Key. Located in a very popular subdivision on Lagoon Drive with deep boating access.This home is 'five stars' the moment you pull into the paver circular driveway. Sitting on two...
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1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo...
Featured review
Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.
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Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings....
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Named one of the most romantic destinations in the world, this Magnificent brand new home in the heart of Islamorada is nestled between Cheeca Lodge Resort and Caribbean Resort offers a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from...
Featured review
Had a great time! The house was amazing and well-appointed. We grilled, we cooked, amd we walked to several great dinner spots. The pool was excellent with the grandchildren. Highly recommended!
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The Conch House is a very special little piece of paradise located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard!! It sits on the open water on Pine Channel on the Gulf side of the Keys. The newly constructed cement L shaped dock can accommodate up to a 32’...
Featured review
House was great, nice layout, pool and view. We had a wonderful time. I would have liked a dock to fish in deeper water from, more reeks and grass beds here. Beautiful though, great host
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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First time offered - only property of its kind the keys -as featured in Global Mansion - Wall Street Journal. A true resort style peninsula surrounded by over 25 acres of park nature, providing the upmost privacy anywhere in the world.Web:Feel the joy of living on a truly beach home. ...
Featured review
We spent a month at this spectacular piece of heaven. It feels like you’re on our own island. Everything was laid out for us and the views anywhere on the property were breathtaking! One of our most...
Distance to beach: 3 miles to Sombrero
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Special Rate for week of April 18-25th!! $1800 ALL IN!Plan your Marathon Trip - Stay at Manatee Cove-4BR/2BA vacation home. Pool with 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...
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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Welcome to Casa Del Sol, a Key West Vacation... your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex.Truman Annex is Key West's premier waterfront community, bordered on one side by Old Town's...
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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....
Featured review
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: 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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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...
Distance to beach: 0.3 miles to Ft Zachary Taylor
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Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on...
Featured review
We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not...
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The Blue Manatee (formerly Sunshade Villa), located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool and all the amenities you can imagine...
Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach
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Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always received great reviews on cleanliness and the bright citrus pallet is welcoming, there are 2 bedrooms (1 King & 1 Queen), one bathroom with couples walk in shower, The small but...
Featured review
Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.
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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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