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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...
Distance to beach: 1 miles to Anne's Beach
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Secluded Waterfront Apartment with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this...
Featured review
Wish we could stay longer. Three months was not enough. Enjoyed the proximity to many Keys activities and restaurants, from Key Largo to Key West.
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Lovely ocean views at Lindsay Landing…A new ocean front home with views from every room! Right in the heart of Marathon, the location couldn’t be better, this home is close to grocery stores and restaurants, and you can walk to the new Children’s Rotary Park at the end of the street. This...
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Emerald ShoresWelcome to your dream getaway at this direct oceanfront vacation rental in Marathon, Florida Keys. This stunning 5-bedroom, 4-bathroom home offers panoramic Gulf and Ocean views, a private heated saltwater pool, an outdoor kitchen, and a private boat slip at the community marina. Designed...
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OWNER PAYS 12.5% TOURIST TAX ON YOUR BEHALF - $0. CHARGES ADDED TO YOUR RATECasa Atlantic is located in the upscale Casa Marina District on a quiet shrub lined street that has very little traffic because it is not a through street. This luxury house that was built in 2013 with 1,672 sq. ft. of finished...
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Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a blend of modern luxury and coastal charm. From top to bottom, no detail has been overlooked in creating this immaculate vacation retreat.Relax and unwind in the spacious living areas...
Distance to beach: 1 miles to Fort Zachery Taylor State Park
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924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy...
Featured review
Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great...
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Privacy galore at this great location on Sombrero Beach Rd with a brand new POOL! Famous Sombrero Beach is approximately half mile down the dedicated bike path from this stilted 3 bedroom single family pool home with dockage! Open concept living with expansive decks on both floors that boast open water...
Distance to beach: 9 miles to Bahia Honda
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Enjoy the Florida Keys in this beautiful canal front two bedroom two bath house in a beautiful area on Little Torch Key. The house features a master bedroom with a king size bed, flat screen TV, and the second bedroom also has a king size bed. A well designed and fully equipped kitchen with everything...
Featured review
We enjoyed our stay in this extremely comfortable home. Beds were very comfortable and location was close to lots of restaurants and local attractions. Having a place for our boat was the best. We could...
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Welcome to Palms & Pina Coladas where you will enjoy a beautifully remodeled waterfront paradise. Located in coveted Cudjoe Gardens, this ground level home comes equipt with everything you need for a relaxing Florida Keys Vacation (Including being able to use our Clear 2 seater Kayak). Private heated...
Distance to beach: 600 yards to Simonton Street Beach
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Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen...
Featured review
Management was informative and responsive. The home was perfect for our needs. Everything was pristine and well cared for. I would give this rental and the management the highest recommendation.
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Fresh, clean, updated and excellent deepwater boating with expansive canal views is what you will find in our newest addition to our Coco Plum Beach neighborhood! Just minutes down the bike path to sandy Coco Plum Beach! This 3 bedrooms 2 bathroom home is just what you've been looking for in a vacation...
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Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean...
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Emerald TidesWelcome to Emerald Tides – a brand-new luxury vacation rental in Marathon, Florida, located in the exclusive Emerald Flats community. This oceanfront escape offers breathtaking open water views of the Gulf of Mexico, a private pool, premium dockage, and upscale interiors that reflect...
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Welcome to your ideal getaway in Key Colony Beach, FL! This charming 2-bedroom, 2-bathroom half duplex is brand new to the vacation rental market and offers everything you need for a relaxing and unforgettable stay. With deep water dockage, you’ll have easy access to the sparkling waters of the...
Distance to beach: 2 miles to Sombrero
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Start planning your perfect escape to the Florida Keys! Flamingo Palms Cottage is ideally located on a deep-water canal with 35’ of dockage and easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas, cozy...
Featured review
The home was very comfortable, and clean, it was so nice to look out the windows and see the water. Everything you need for cooking in is provided as far as dishes and pots and pans. Also, the Canopy...
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Welcome to Reel Life, a beautiful Cudjoe Gardens Oasis! Located on the ocean side of Cudjoe Key, this home has everything you need to enjoy a true Florida Keys vacation! It features an in-ground heated pool, a large Tiki hut/bar for hanging out by the pool, a wood dock to accommodate your boat, a sandy...
Featured review
I have been going here for years. We enjoy fishing the back country, and it is right on the gulf. It is a great time to get to enjoy family.
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Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking distance...
Featured review
171 10th St. The duplex was very neat. We loved the screened in back porch (had to keep the fans going because of the heat). The pool chairs lacked comfort but we had seen that in the pictures and brought...
Distance to beach: 800 yards to Ft. Zachary Taylor State Park
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Note: Minimum stay is 28 nights. Saturday-to-Saturday arrivals and departures required by Homeowner Association rules. No short weekend stays permitted. Pets by special permission.About This Property A Touch of Bermuda is a privately owned, two-story Bermuda-style conch cottage in the Shipyard section...
Featured review
Our stay for the month was perfect. A Touch of Bermuda has everything a guest could want in a perfect Key West location. However, the best part of our stay was dealing directly with the owner (Jack) throughout...
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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...
Distance to beach: 5 miles to Sombrero Beach
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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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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...
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Welcome to Salty Skies on Sombrero, your ultimate tropical paradise, just steps from the white sands and turquoise waters of Sombrero Beach! This stunning 4-bedroom, 3-bath retreat combines luxury, relaxation, and adventure in the heart of the Florida Keys.Outdoor Bliss for Every OccasionStep...
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Adorable 2 bedroom, 1.5 bathroom half duplex. Conveniently located at the top of 4th Street in exclusive Key Colony Beach. Nicely updated, fresh and bright! Walk to the Cabana Club and enjoy the complimentary membership with a large swimming pool, bar/restaurant, beautiful sandy beach. Excellent deep...
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Welcome to Kokomo Palms – Your Island Escape!Discover the perfect slice of paradise at Kokomo Palms, a charming 2-bedroom, 1-bath vacation home nestled in Big Pine Key. Located in a peaceful canal-front neighborhood, this getaway offers everything you need for a relaxing and adventurous stay....
Featured review
We had a great time - the rental was terrific! Best clostet space we've ever encoutered. Clean laundry set. Accomadotions were top shelf all around. Nicely seculed & quiet location. And we saw Key deer...
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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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Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive Morton St. Enjoy the magnificent open Gulf views from nearly every room. This unique home is reminiscent of the way the Keys used to be…..charming! Perfect area for walking,...
Featured review
Had a great family week at this lovely home with pool, hot tub and tiki hut. The furniture was comfortable and the kitchen was great. We visited many of the local state parks and beaches, the restaurants...
Distance to beach: 1 miles to Cabana Club
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Lovely full duplex that sleeps 14! Upstairs there are 3 bedrooms, 2 and a half bath’s with a wide open concept. The half bath is off the living room area. Four flat screen TV’s, hi speed wireless internet, gas grill and a lovely pool (heat is $200/wk optional). Pool is 10 X 20 and 4′...
Featured review
The location is great! The home, yard, and pool are beautiful. We would recommend the place to others.Some minor issues that should be addressed: the outside fish / bait cooler was very dirty and unusable...
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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.
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Forget your worries in this spacious and serene space. Enjoy all that Marathon has to offer in this perfect location within walking distance to Cocoplum beach. This spacious completely renovated 2 bedroom condo offers everything that you will need for your vacation rental. Offering a boat slip right outside...
Featured review
Fantastic condo in Marathon. Great location with its own community boat ramp, a dock right next to the condo, a pool, and a nice sandy beach a very short walk away. The best part was Katie Carillo the realtor...
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Stay right on Bonefish Bay in this spacious 4BR / 3BA waterfront home with two master suites. Bring your boat and enjoy a 70-ft dock with quick ocean access just 1 mile away. Relax in the private heated pool, fish from the dock, and enjoy peaceful waterfront views. Perfect for boaters, anglers, and families...
Featured review
The title says it all. We all agreed we would stay here again in a heartbeat! The house was clean and well maintained. The kitchen was well equipped though we had a little bit of a learning curve figuring...
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Welcome to Pirates Quay! This newly remodeled 2 bedroom home in Little Torch Key is one of the nicest, most thought-out properties in the area, and with extra living space downstairs and plenty of storage, it feels much bigger than it is. Its pirate theme can be seen throughout from the decor, colors...
Distance to beach: 6 miles to Baja Honda
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Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances,...
Featured review
My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live...
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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,...
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Emerald HorizonExperience elevated coastal living in this luxury 5-bedroom, 4-bath vacation rental in Marathon, Florida Keys, designed for large families and groups seeking premium comfort, modern design, and Gulf-access adventures. Located in the new community of Emerald Flats, this home includes...
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Brand-new construction, expertly decorated single family home in Marathon. Whether you are vacationing with family, embarking on a fishing trip or looking to just relax Florida keys-style this is the perfect home for you. This spacious 1,800 square foot single-level stilt home offers 4 bedrooms, 3 full...
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This charming one bedroom cottage has everything you need. Full kitchen and living area to relax in. Outdoor backyard patio with gas grill. It is an easy walk to shopping and dining. If you have a car, this property offers a private parking space for your convenience. Please note this is a monthly...
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$15,000-$17,500 WeeklyA world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute...
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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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Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —Units 201 and 203 rented together. Private steps to pool, beach and Atlantic Ocean! 8 bedrooms, 8 full baths, 2 half baths, 2 full kitchens, 2...
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Beautiful bayfront house, private pool and dock, right in Downtown Islamorada Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern finishes meld with traditional Key West style, Coral Cove 8 offers island living in style. This retreat is...
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Charming 3-Bedroom, 2-Bathroom Duplex with Waterfront Views in Key Colony BeachEscape to this inviting ground-level duplex home in the heart of the beautiful Key Colony Beach. With stunning waterfront views, top-notch amenities, and plenty of space, this charming retreat is ideal for families or groups...
Distance to beach: 3 miles to Sombrero Beach
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*Modern updates, new furniture, new docks, pool etc- updated photos on mgmt site!* A spacious bayside 3 BR 2.5 BA retreat within Indigo Reef, a private resort community of Marathon FL- offers many extras for anglers, families, snowbirds, or tourists! Beautiful views from both levels of canals, spacious...
Featured review
Our stay at Indigo Reef was fantastic. Perfect weather and a perfect location. The unit had everything that we needed and was very comfortable for 5 adults. We truly hope to be back for a longer stay in...
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Elegant Florida Keys direct ocean access and some open water views from the dock and balcony. This property is single family elevated home. All rooms and bathrooms are upstairs. 40 foot dock with 4 cleats. Large driveway, parking for at least 6 cars, trailer and RV. 75' of waterfront with wood dock....
Featured review
Can’t say enough about Maria and Daniel the owners. They catered to us from first contact. The place was spotless and the home is even nicer than the pictures. It was a short visit for my wife and I,...
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***SUMMER SPECIAL*** August-November $500 off regular price! Don't wait, books fast. Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons ( **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of...
Featured review
I had the pleasure of staying for the month of December. I've been staying in the keys during the month of December for the past 5 years and this is by far my favorite place! The condo was warm and inviting,...
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This lovely, brand new home is located in a private, quiet residential area just 3 blocks from Sombrero Beach and 5 minutes or less to the open Atlantic by boat! 3 bedrooms and 2 baths, all tiled floors, pretty kitchen with granite tile counters. The master bedroom has a queen bed and en suite bath with...
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Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach,...
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Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom home offers a serene escape with breathtaking Gulf views and a perfect location for relaxation and adventure.*Saturday-to-Saturday Rentals OnlyProperty Overview: Prime Location: Tropical...
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Welcome to Reel Therapy, a beautifully updated three-bedroom, three-bathroom ground-level half duplex located on the tranquil side of 9th Street. The spacious bedrooms include a master suite with a king-size bed, a queen bed in the second bedroom, and two doubles in the third bedroom. Entertainment is...
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