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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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WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!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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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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Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports...
Featured review
We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf...
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Relax amongst the tropical sights and sounds in this charming ocean front condo.Ideal for couples, solo & budget travelers, Key West Road Trippers, Snowbirds, Sea-Foodies, Divers, Snorkelers & AnglersSEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME!The space With thoughtful and...
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Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a grand open-concept layout seamlessly blending living, dining, and a wet bar, all framed by panoramic seascapes, a chef's kitchen and access to top-tier...
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
We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!
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Enjoy Beachfront Island Life from our condo right on the Atlantic Ocean. We are literally only 10-20’ from the water depending on the tide.Totally remodeled in 2022. All new kitchen with high end appliances. Beautiful master bath with large walk in shower for two.Huge wrap around...
Featured review
Clean and fully renovated with wraparound balconies overlooking the sandy beach and palm trees. Amazing sunrises and sunsets over the ocean. South and west facing windows. Great beach and communal pool....
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Special discount for stays of 2 weeks or more!There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned...
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Sun Kissed Tails is a beautiful 3 bedroom 3 bath townhome, with a modern coastal feel, in the Hawks Cay resort on Duck Key, MM61.ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 min drive to Key Colony Beach. The Cabana Club has an olympic size pool, Tiki Bar and restaurant, ocean...
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WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!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...
Distance to beach: 2 miles to Sombrero Beach
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Waterfront Keys home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, half-duplex home with private pool, dock with great amenities - perfect for three couples or a family. Great location that's walk-able to the 7-Mile bridge and some of Marathon's best restaurants and bars. Incredible...
Featured review
We absolutely love staying at this property! We rented a boat for the week this visit and it was so nice to walk past our private pool and jump in our boat or fish right off the dock. Manatees swim by almost...
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Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and luxury. Ocean Residences blends modern touches with a secluded retreat atmosphere, providing the ultimate getaway experience. As our vacationer and a new addition to our family, you'll enjoy seamless comfort...
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...
Distance to beach: 1 miles to Sombrero Beach
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Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9:00 AM. Check in directions are emailed to you the week prior to your arrival { please check "spam" } Pups...
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Tropically furnished condominium with amazing views of the Gulf of Mexico, located at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. It is centrally located, with easy access to Restaurants, shopping...
Featured review
We had great time. The weather was perfect and everyone there was friendly and help full. Also are host Nancy was very help full from start to finish. We did some great fishing in the gulf; everglades and...
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3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key WestThis charming Conch house features a queen bed in the master bedroom, a queen bed in the first guest bedroom, and two queen beds in the second guest bedroom. The kitchen has been beautifully renovated, and there is a wonderful...
Distance to beach: 2 miles to Founders Park
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This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios...
Featured review
This was the nicest home overall I have rented. If you have a boat, don't look elsewhere. Everything in the house functioned and the house had everything one would need, even for people who do cook while...
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We would like to invite you to stay at our peaceful keys getaway. Enjoy the spacious porch overlooking the pool and canal, this is great for my wife and I to watch our kids while they are swimming and fishing off the sea wall. As you can tell by the pictures you can catch hugh snapper right off the sea...
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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...
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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...
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
We could not have asked for a better place to stay. The hosts were absolutely amazing. The lazy river pool was our favorite place to be. The grill ran out of propane one night and we messaged the host and...
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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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WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!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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Welcome to Paradise Palms – the crown jewel of the exclusive Peaceful Palms gated community. This newly built, three-story luxury oceanfront home delivers a rare blend of modern elegance and unobstructed ocean views—all just steps from the water. Every detail reflects our commitment to comfort,...
Featured review
Best stay we’ve ever had in the Keys and we booked super last minute. We always choose Islamorada, but this place blew every other stay out of the water. The third-story balcony was insane—hello ocean...
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Welcome to your dream coastal escape! A peaceful and beautifully well maintained home where comfort meets adventure. Beautiful 3-story canal-front home, just 3 houses from the ocean. Boaters Dream!! Including an entertainment room, ideal for an executive office or a private guest retreat with sofa bed....
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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This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every...
Featured review
We had a great time, we will definitely be back! Fun in the sun! Close to restaurants and grocery store.
Distance to beach: 0.5 miles to South Beach
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This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill...
Featured review
This small unit had everything we needed. Very clean and convenient to everything we wanted to do. Will rent again! Pam was so easy to work with.
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Welcome to 137 Mockingbird Cove! Modern, expansive home built in 2022, offering incomparable boating! Quick walk or ride from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles,...
Distance to beach: 8 miles to Sombrero Beach
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Welcome to Marlin House – your perfect Keys getaway! This 2-bedroom, 2-bath coastal retreat offers the perfect balance of comfort and adventure. Relax in your own private plunge pool, enjoy fully stocked amenities for a stress-free stay, and make yourself at home with thoughtful touches throughout.Step...
Featured review
Was the perfect place to stay visiting my grandson!’ It was so clean, we loved the pool. It was fully stocked! Will be definitely book again at our next trip! Fabulous!!
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Must See Stunning 3095 Sq. Ft 4/4 SFH on ground level with pool, 45 ft of dockage, outdoor kitchen and access to the ocean by boat.This gorgeous property features an open floor plan with elegant furnishings, state of the art kitchen with Viking appliances and an induction cooktop, quartz countertops,...
Featured review
I didn’t know much about Marathon other than it was in the keys. Upon hearing from a family friend that it was the Keys best kept secret we couldn’t resist. The Sunny Daze house was perfect for my family...
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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....
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Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...
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WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!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...
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WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST!"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), private dock (up to 35' boat), fish cleaning...
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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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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WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!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...
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 THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!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...
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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Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2...
Featured review
The condo was neat and well furnished. Great location and a beautiful property! Founders park across Rt 1 is a great take with a nice beach and very helpful staff at the visitors center.
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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: 6 miles to John Pennekamp State Park
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1 BR/1 Bath Rare Find! Lovely oceanfront home with large private boat basin. This ground-level house has two enclosed sleeping areas - a master bedroom with a king bed, and a private alcove providing sleeping space for up to 4, with 2 bunks and a full-sized bed (separated from the living room by an...
Featured review
A lovely property, a comfortable house with all the amenities and a covered outdoor patio right on the ocean where we spent most of our time reading, sunning, and watching the wildlife fly, swim and crawl...
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Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. It’s located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south....
Featured review
I was lucky enough to stay here December and part of January! EXCELLENT owners. AWESOME pool area and a WONDERFUL comfortable home!!! Has everything you need and then some! It is close to Key West and...
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This Condo comes with a 30' Boat slip, 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.
Distance to beach: 2 miles to Sombrero Beach
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A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround...
Featured review
Will definitely be back to this house. The house was perfect! We saw manatees, lots of sea turtles, tropical fish and caught a tarpon! The house is ideally located and very private. We had a fabulous two...
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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! Although there are two attached units, each have their own private amenities and parking. There is a 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.
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DescriptionAdorable two bedroom, two bathroom half duplex on stilts overlooking the extra wide, deep canal and the Par 3 Golf Course on the streetside. This home is tidy and spacious. It offers soaring ceilings, tons of natural light, lots of covered seating, a beautiful concrete pool, 37 feet of...
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
A large, well-designed home with a great location on a canal offered 9 of us (ages 17 to 83). a fun filled week. Several of us enjoyed the nearly 4-mile walking path across the road. Easy access to the...
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2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping,...
Featured review
The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used...
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Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos...
Featured review
Beautiful sanctuary centrally located in Old Town. Very comfortable accommodations in a well maintained property. Property manager and Owner were very responsive to any questions or concerns that arose....
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