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About this property
Beautiful , home on deep water canal in desirable Breezeswept Estates is your private resort for a minimum of 28 days . Heated, saltwater pool adjoins huge ground level great-room with living area, dining area, shower , gas grill, pingpong table and so much more contained in private setting ! 40 ft dock ...
Property Type
Ramrod Key House
Featured review
Very nice pool & dock area. Neighbors very friendly. Downstairs area very nice for socializing near pool area. House was comfy for family with adults & children. A great location for restaurants ...
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Welcome to Flamingo Island Paradise!Step into this updated spacious home and enjoy! Tasteful, fresh decor matched perfectly for this relaxation paradise. 2 Master suites with ensuite bathrooms and comfy King Beds. There is a pullout twin in the living area for an extra guest. Updated well stocked ...
Property Type
Marathon House
Featured review
This is a great location for two couples exploring what the Florida Keys has to offer. We did not have a boat or plan to fish so the residence could’ve accommodated both of those things. We did use the ...
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Come and enjoy a tropical sanctuary at this beautifully remodeled, fully furnished ground level island home located in Big Pine Key, Fl. Situated on a quiet street, this home features a bright, open interior with 3 bedrooms, 2 bathrooms. The yard is a wonderful oasis overlooking the canal with a hot ...
Property Type
Big Pine Key House
Key Amenities
About this property
** SUMMER SPECIAL $1800/WEEK**Relax in this peaceful 2/2 with incredible ocean and sunset views! Welcome to Sunset Paradise!Not 1 but 2 spacious and comfortably furnished decks with a water view. Everything located right on the waterway, complete with a private 40 ft boat dock.Unique Fun ...
Property Type
Key Colony Beach House
Key Amenities
About this property
This 3 bedroom 2 bath home is located on Cudjoe with easy access out to the open water. Bring your boat up to 26`and take out the kayaks provided at this home. There is ample room for outside activities, a BBQ grill and downstairs bait/beverage refrigerator.The master bedroom has a king bed and there ...
Property Type
Cudjoe Key House
Distance to beach: 0.7 miles to Coco Plum Beach
Key Amenities
About this property
Beautiful Bonefish Yacht Club 3/3 townhome! Overlooking the waterfront marina, this 3 story townhome, end unit has been thoughtfully updated and curated for a tranquil hotel experience with all the comforts of home. We welcome you to ask questions and look forward to having you as our guest!We fell ...
Property Type
Marathon Townhome
Key Amenities
About this property
Sanctuary in Paradise Unique property featuring: ~1BR 1BA main house ~2BR 2BA downstairs apt. ~1BR CottageWhether your ideal vacation is relaxing in a hammock in view of the ocean with a good book or hosting parties late into the night, Sanctuary in Paradise can accommodate you. We have a quiet ...
Property Type
Plantation Key House
Featured review
Andy was a wonderful host and his property was gorgeous. My family, including kids and grandkids took full advantage of the water access and all of the fun amenities. There was plenty of room for our two ...
$399
avg/night
Key Amenities
About this property
NEW TO MARKET AND AVAILABLE FOR LOBSTER MINI SEASON!!! This new construction has everything. This concrete house is waterfront with great views of Bonefish Bay. The 70 foot dock is built in 10-12 foot water. It is frequented by manatee, dolphin, and numerous mangrove snapper. The large heated pool ...
Property Type
Marathon House
Featured review
Great place!! Loved it . Parking is tight, They do have trailer storage offsite. Jessica was easy to work with and highly recommend contacting her!!!
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About this property
This brand new 5/6 bedroom 4 bath oceanfront home has a private pool and will share dock space, kayaks and the gazebo with Blue Palms Retreat home. There is 1 double and 3 single kayaks. Bring your boat- up to 24’ and your snorkel gear. Relax on one of the porches overlooking The Atlantic Ocean ...
Property Type
Cudjoe Key House
Key Amenities
About this property
Casa Del MarDreaming of a Marathon Florida Keys Vacation Rental? This is the home to turn that dream of a Florida Keys vacation home into reality! Only an hours’ drive south of the continental United States you will find Marathon, in the Florida Keys, an island a world apart from the fast ...
Property Type
Marathon House
Distance to beach: 0.5 miles to Sombrero Beach
Key Amenities
About this property
Exclusive Sombrero Beach vacation retreat is located just up the street from one of the best beaches in the Florida Keys. Sombrero Beach is a large sandy beach that offers something for everyone in the family including playground, volleyball swimming and picnic tables. The beach is also a great place ...
Property Type
Marathon House
Key Amenities
About this property
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 the world, Islamorada. If you have never experienced summer in the Keys, you might be surprised! ...
Property Type
Islamorada Condo
Distance to beach: 3 miles to Sombrero Beach
Key Amenities
About this property
Casa PlayaWelcome to Casa Playa, a luxurious 4-bedroom, 4.5-bathroom home in Marathon, Florida. Nestled behind gates in a 4-home enclave, this custom-designed retreat offers an element of luxury with stunning views of the canal and the open ocean. With technology throughout, a private pool with a ...
Property Type
Marathon House
Key Amenities
About this property
Charming half duplex with 45.5' of seawall. Fish cleaning table, with electric at the dock, and bait freezer. Locked storage for all your fishing gear. There is a FABULOUS under water light at the dock for amazing views of the fish life in the canal.Master suite with a king size bed, and bathroom ...
Property Type
Key Colony Beach House
Featured review
We live in SW Florida and wanted a quick summer trip to the keys. This house was perfect for our family. Just enough space for our family of 4 to relax and enjoy the view. The pool was great to dip in ...
Key Amenities
About this property
Manatee Love awaits you! Nicely updated, spacious 3 bedroom, 3.5 bathroom canal front home on beautiful Key Colony Beach. Enjoy over 1,650 square feet of open concept space, large living area overlooking the wide, deep canal, brand new kitchen and appliances, granite countertops, and a Keurig! Well-equipped ...
Property Type
Key Colony Beach House
Key Amenities
About this property
Come enjoy this beautiful OCEAN VIEW condo located in Key Colony Beach on the 2nd floor!!! This two bedroom & two bathroom condo offers all the amenities of home!!! Enjoy a cup of coffee in the morning, or a glass of wine anytime on one of the two ocean view balconies. Coin laundry right outside the ...
Property Type
Marathon Condo
Key Amenities
About this property
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 ...
Property Type
Summerland Key House
Distance to beach: 10 miles to Bahia Honda
Key Amenities
About this property
Our spacious custom built 2 bedroom and 2 bathroom newly renovated home awaits you. Located in the heart of the National Key Deer Wildlife Refuge. On the water with direct access to the Gulf of Mexico or to the Atlantic Ocean. Concrete Seawall with step down easy boat and kayak access. Fish Cleaning ...
Property Type
Big Pine Key House
Key Amenities
About this property
Our Cancellation policy is: Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be ...
Property Type
Little Torch Key House
Featured review
This property is about a half hour north of Key West....perfect for relaxing but close enough to go to town and enjoy the party and any boat trips you might want to take. We would consider renting it again. ...
Key Amenities
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No detail spared in this completely renovated, top of the line stilted half duplex on 9th Street in highly sought after Key Colony Beach. Excellent end of the canal location makes for instant access to Vaca Cut! Head to the open waters of the Gulf or Atlantic! Open concept living and kitchen area overlooking ...
Property Type
Key Colony Beach House
Key Amenities
About this property
Suncatcher on the ocean is new to the rental pool at 1800 Atlantic. A fabulous property with many upgrades throughout. Totally renovated from top to bottom with high end finishes and no attention to detail spared. We are excited to offer it for rent for the first time. Tastefully decorated in Island ...
Property Type
Key West Condo
Key Amenities
About this property
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’ ...
Property Type
Little Torch Key House
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
Key Amenities
About this property
Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited for large boats and there is tons of dock space for all your water toys! There is plenty of parking as well, enough for trailers and RV's. The pool is private and very large....kids ...
Property Type
Summerland Key House
Key Amenities
About this property
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 ...
Property Type
Marathon Condo
Featured review
Our family of four had an amazing 10 days in this condo! The double beds in the kids’ meant they didn’t have to share a bed. The condo was very clean and well appointed with everything we needed. It’s ...
Key Amenities
About this property
This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space ...
Property Type
Summerland Key House
Key Amenities
About this property
This 3 bedroom/2.5 bath home is located in a quiet neighborhood on a deep canal with easy boating access to open water.The Master has a King bed, 2nd bedroom has a Queen. There is an extra sleeping area with a queen and twin bunk bed, 1/2 bath and outdoor enclosed shower. 2 beach bikes and 1 double ...
Property Type
Little Torch Key House
Distance to beach: 0.2 miles to Fort Zachary Beach
$440
avg/night
Key Amenities
About this property
AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. POOL within 1 walk of condo. We rent for 7 days or more, monthly113 ...
Property Type
Key West Condo
Featured review
My husband and I enjoyed 8 nights in July at the Shabby Chicken. The condo had everything we needed and couldn’t ask for a better location!
Distance to beach: 3 miles to Sombrero Beach
Key Amenities
About this property
Under new ownership & management *Modern updates, new furniture, brand new docks, pool etc- updated Photos soon!* A spacious bayside 3 BR 2.5 BA retreat within the Indigo Reef resort community with many extras for anglers, families, snowbirds, or tourists! Beautiful views from both levels of canals, ...
Property Type
Marathon Villa
Featured review
One of the nicest places we’ve been to and hope to come back soon we had everything we needed and more clean updated comforts of home we fell in love with everything and couldn’t have had a better vacation
Key Amenities
About this property
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 ...
Property Type
Marathon House
Key Amenities
About this property
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' ...
Property Type
Cudjoe Key House
Key Amenities
About this property
Just a few houses off Duval, this wonderful retreat occupies the upper level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. The carefully restored Dade County Pine wood walls and Red Oak floors evoke a more relaxed era in the Southernmost City. The home opens ...
Property Type
Key West Apartment
Distance to beach: 1 miles to Fort Zachery Taylor State Park
Key Amenities
About this property
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 ...
Property Type
Key West House
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 ...
Distance to beach: 1 miles to Cabana Club
Key Amenities
About this property
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′ ...
Property Type
Key Colony Beach House
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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About this property
Peace at 7 Knots... The newest house on Sombrero Beach Road! Be the first to stay at our lovely home. It is wonderfully decorated with a "more is less" clean style while at the same time having all that you will need in a single family home located in Marathon. Whether you are vacationing with ...
Property Type
Marathon House
Featured review
This is the second time renting this house. The location and all the amenities make this the perfect house to rent in Marathon for. The pool is great size. Ample parking for guest and boat trailer. The ...
Key Amenities
About this property
NEW TO MARKET AND AVAILABLE FOR LOBSTER MINI SEASON!!! This new construction has everything. This concrete house is waterfront with great views of Bonefish Bay. The 70 foot dock is built in 10-12 foot water. It is frequented by manatee, dolphin, and numerous mangrove snapper. The large heated pool ...
Property Type
Marathon House
Featured review
You and your friends and family will love this paradise.. Stayed here 4 times already. Don't pass up the opportunity to see for yourself!
Key Amenities
About this property
Come relax with us in this adorable two bedroom, two bath half duplex on the shady side of 9th St. Brand new pool that is 9 X 16 and 3' to 4' in depth. There are three therapy jets on the seating area like a whirlpool.The master bedroom has a king size bed, while the guest bedroom has a ...
Property Type
Key Colony Beach House
Distance to beach: 15 miles to Bahia Honda
Key Amenities
About this property
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on ...
Property Type
Cudjoe Key House
Featured review
Well kept clean condo and good host. The host has a nice binder with information and local things to do with mile markers. I would have liked to have the list emailed to me before we came to plan more ...
Distance to beach: 5 miles to Sombrero
Key Amenities
About this property
Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and not one detail has been overlooked. It is every renter's dream.Luxury and tranquility await you in this beautiful 3BR, 2.5 BA home at Indigo Reef Marina, named one of Marathon, ...
Property Type
Marathon Villa
Featured review
Indigo Reef #41 quickly became our family’s new favorite place to stay. This was our second trip to the Keys and this house was amazing. The attention to detail cannot be overlooked. The owner (Toni) ...
Key Amenities
About this property
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, ...
Property Type
Key Largo House
Key Amenities
About this property
Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Key – Bahia Azul, “Bay of Blue” is exactly the ...
Property Type
Summerland Key House
Featured review
Great home on a canal with easy access to the ocean. The extensive dock is wonderful. Very comfortable home with with a good flow.
Key Amenities
About this property
Recently Renovated!! Our unit is a spacious 2 BR 1.5 BTH located on the 3rd floor overlooking the bay. Enjoy amazing views of the sunset from the balcony or dockside at our marina.Key Largo is home to amazing restaurants, bars and local attractions. Everything is within a short walk, bike, drive ...
Property Type
Key Largo Apartment
Distance to beach: 8 miles to Bahia Honda State Park in the keys
Key Amenities
About this property
Ocean access waterfront canal with 40’ dock and all the fixins. Looe key reef straight out canal. 2/2 house with nice size porch
Property Type
Ramrod Key House
Featured review
I was really worried house was going to be too small, as it is a 2 bedroom. We ended up having plenty of room. Beds were very comfortable and A/C would freeze us . Dock was plenty big for our 35’ center ...
Key Amenities
About this property
This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitchen and living room. Relax in your outdoor oasis at the water's edge before heading out to scuba dive, shop, fish, or even embark on a lobstering adventure.Located on Pine Channel, ...
Property Type
Little Torch Key House
Key Amenities
About this property
This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented ...
Property Type
Key West House
Key Amenities
About this property
Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking or paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, ...
Property Type
Key Largo Townhome
Key Amenities
About this property
Welcome to Villa Bella an updated cozy 3-bedroom 3 bath duplex with a private heated pool in the heart of Key Colony Beach steps away from Sunset Park. The master bedroom suite has a King size bed with attached bathroom. The second bedroom is a Queen size bed, and the third bedroom offers 2 twin beds. ...
Property Type
Key Colony Beach Villa
Key Amenities
About this property
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 ...
Property Type
Marathon House
Distance to beach: 5 miles to Anne's Beach
Key Amenities
About this property
Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath ...
Property Type
Islamorada Condo
Featured review
This condo is a great location for families to enjoy the water activities and the many great restaurants in the area. It has an awesome view of the ocean and local bridges. Condo has all the amenities ...
Distance to beach: 5 miles to Founders Park
Key Amenities
About this property
Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees ...
Property Type
Islamorada House
Featured review
The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...
Key Amenities
About this property
Check out Anglers at Sombrero Canal Front Townhome with a private pool and 30 ft of dockage! Just minutes to the stunning Sombrero Beach, this Villa-style home is perfectly located in the heart of the Florida Keys. This newer built villa offers beautiful views of the canal and surrounding neighborhood. ...
Property Type
Marathon Townhome
