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Welcome to your private slice of paradise in Key Largo. Nestled in a quiet, well-protected canal-front neighborhood, this beautiful four-bedroom home offers the perfect escape for those seeking comfort, space, and the laid-back charm of the Florida Keys. Designed to accommodate up to 10 guests, the home...
Key Amenities
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Welcome to Croton Lane Retreat! This comfortable home is located on a canal with 2 bedrooms (Queen beds) and 2 full bathrooms. It has a beautiful screened-in porch with comfortable seating for relaxing and an outdoor dining table with seating for 6 for comfortable outdoor dining. The house has central...
Distance to beach: 3 miles to Founders Park
Key Amenities
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Welcome to Blue Palm Oasis!Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantation Key in Islamorada. This contemporary Keys villa seamlessly blends modern comfort with laid-back island charm, making it the perfect place to unwind, recharge, and soak up the sun....
Key Amenities
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The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...
Featured review
I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to...
Key Amenities
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Multi-million dollar views and the peace and quiet you expect in the Keys. DIRECT bay front condo, white sandy beach, new gym, sauna, swimming pool, bocce, basketball and tennis courts, non motorized water sports launch area and storage, native tropical paths, numerous hammocks and seating areas on the...
Featured review
Absolutely loved my time here! The condo has all updated bathrooms, kitchen and laundry! The master bathroom is beautiful and felt like I was in a hotel! Views are gorgeous and the location is great! Will...
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Key Amenities
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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: 0.8 miles to Fort Zachary Taylor State Park and Beach
Key Amenities
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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.
Key Amenities
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Lady Grace will not be in Florida for the 2025-2026 season. Come visit her in the BAHAMAS!Bahama Cruise with exploration in the Exuma IslandsFor guests who want to enjoy a vacation on the move, our cruise aboard Lady Grace is for you. Nassau, Bahamas is the center of our winter cruise program,...
Featured review
The Lady Grace was awesome and Kelly and Capt Jamie were phenomenal. Everyone loved the yacht and everything she had. Plenty of beds bathrooms and gathering places. The sunset cruise was excellent and so...
Key Amenities
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This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get together. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood floors throughout. 3 large...
Featured review
We thoroughly enjoyed our stay at Palmetto Retreat. The home was spotless and had all the amenities we needed. A couple of menial things didn't work, and Christine (Rudy) took prompt care of them while...
Key Amenities
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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...
Key Amenities
About this property
This vacation home has a spectacular view over Cudjoe Bay to the Atlantic from the upper deck, and from the seats in the heated private pool. Kayaks included in the rental. Home has 4 bedrooms and 2 bathrooms. Property has water access/dock for a small boat, and options to dock a larger or multiple boats...
Key Amenities
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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...
Key Amenities
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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...
Key Amenities
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Welcome to Margarita Manor – Your Tropical Escape in the Florida Keys!Set your watch to island time and relax at Margarita Manor, a vibrant waterfront oasis perfectly suited for sun-chasers and boating enthusiasts alike. Located just moments from open Atlantic waters, this breezy retreat offers...
Key Amenities
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Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada...
Featured review
A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us....
Distance to beach: 4 miles to Sombrero Beach
Key Amenities
About this property
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...
Key Amenities
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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...
Key Amenities
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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...
Key Amenities
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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 Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you...
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...
Key Amenities
About this property
Newly renovated cottage with million dollar oceanfront views.The beautiful in ground private pool will give the serenity you need for a relaxing escape with unobstructed view of the ocean, you can enjoy breathtaking sunsets, watch boats drift by, and listen to the soothing sounds of the waves—all...
Featured review
I stayed in the newest cottage . It was very clean and every essential needed. Mark was thoughtful enough to put bottles of water in the refrigerator for us . I had coffee every morning on the upper Tiki...
Key Amenities
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Welcome to Casa Caribe, a comfortable 2 bed, 2 bath vacation home on Summerland Key. Located on one of the best canals on the island, and conveniently across the canal from the Summerland Marina, this home provides quick boating to the blue water as well as the prime diving areas of the Gulf and Looe...
Distance to beach: 1 miles to Sunset Park
Key Amenities
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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!
Distance to beach: 4 miles to Founder's Park
Key Amenities
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Welcome to Sunset Oasis!This beautiful bayfront retreat offers a rare blend of comfort, style and waterfront living in the renowned Indian Mound/Plantation Key community.This is a monthly rental. Flexible rental dates. Property is reserved from 11/1/2026 through 3/31/2027.Sunset Oasis is...
Key Amenities
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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...
Distance to beach: 3 miles to Sombrero
Key Amenities
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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...
Key Amenities
About this property
Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside...
Featured review
We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage...
Key Amenities
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Beau Soleil is located in the most sought after neighborhood in the Lower Florida Keys, Summerland Cove, on Summerland Key. A gorgeous gem, tucked away in privacy with tropical plants and fruit trees everywhere you turn!This home is situated on a great boating canal with plenty of dockspace for your...
Key Amenities
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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!
Key Amenities
About this property
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...
Key Amenities
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This charming family-friendly residence in Duck Key presents a spacious and inviting environment, featuring three comfortably appointed bedrooms and three modern bathrooms, making it an ideal choice for a memorable getaway. Each bedroom is thoughtfully furnished with a plush king-sized bed, ensuring restful...
Distance to beach: 1 miles to Sombrero Beach
Key Amenities
About this property
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...
Key Amenities
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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: 3 miles to Founders Park
Key Amenities
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Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...
Key Amenities
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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...
Key Amenities
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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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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...
Key Amenities
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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....
Key Amenities
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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...
Key Amenities
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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....
Distance to beach: 40 feet to Across the street
Key Amenities
About this property
FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT WATER VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, Queen bed in 2ND BEDROOM AND TWIN...
Featured review
This place is amazing, beautiful beach right out the front door is why we come here. The host is the best, Nancy catered to all our needs. The home is nicely decorated, it had everything we needed. We will...
Key Amenities
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"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 station, bait freezer and 4 new bikes! Additionally,...
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!
Key Amenities
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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...
Key Amenities
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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...
Key Amenities
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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
This beautiful, perfectly maintained property was one of our best stays ever. This was our first time in Islamorada and we will be back. The accommodations were spotless, the patio, the view and the hammock...
Key Amenities
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Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...
Key Amenities
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Florida Keys Vacation Rentals – Nestled on a pristine canal-front lot, situated in Little Torch Key, this well-appointed home offers all the amenities you will need to enjoy the casual lifestyle of the Lower Keys. The lovely back yard area has a gas BBQ grill, a dining table with seating for six,...
Key Amenities
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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...
Key Amenities
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You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops.The...
Key Amenities
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This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its tiki bar, expansive sandy playgrounds and lounge areas. Nestled along the tranquil shores of Florida Bay, its array of indoor and outdoor living areas, BRING YOUR BOAT - dock with ocean-access...
Key Amenities
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Water front upstairs Duplex with 38 feet of deep water Dockage ,minutes from open Ocean. two bedroom and 3.5 bath house plus living room with two sofas beds completely renovated, centrally located in prestigious Port Largo Neighborhood, minutes from all water activities imaginable. Enjoy Deep Sea Fishing,...
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