Waterfront holiday rentals in Islamorada

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Islamorada

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Guest favourite

Townhouse in Marathon

4.98 out of 5 average rating, 164 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also, our marina is 100% open and operational should you need to rent a slip during your stay Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house

Guest favourite

Apartment in Key Largo

4.99 out of 5 average rating, 106 reviews

Enjoy sunsets & sunrise in your home away home.

Keys largo best kept secret. Enjoy all that Florida keys have to offer. Superb location close to main land and best of all on the water. Enjoy sunset on your private dock. Don't worry about parking you have you very own private spot. Very close to miami if you wish to venture out off the Florida keys. Great beaches and great restaurants. Come and enjoy the best that Florida has to offer. Great location to relax. You can enjoy the pool, tennis and basketball. You can eat in the club on the water.

Guest favourite

Holiday home in Key Largo

4.95 out of 5 average rating, 102 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Guest favourite

Campervan/Motorhome in Key Largo

4.95 out of 5 average rating, 104 reviews

Paradise Casa Bayfront sunsets,pool,King bed ,dock

Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp with kayak rentals, glass bottom boats, create memories scuba diving/snorkeling.

Superhost

Flat in Key Largo

4.83 out of 5 average rating, 250 reviews

5. Guest's Favorite: Waterfront Apt in Key Largo!

Embrace the tranquil waterfront lifestyle in Key Largo! Revel in picturesque boat views and indulge in freshly caught dishes served at nearby restaurants. Observe the serene presence of manatees, nurse sharks, and a variety of fish leisurely gliding through the canal. Conveniently dock your boat at the Pilot House Marina nearby. Our unit boasts a Modern, Spacious, and Impeccably Clean atmosphere, featuring Private Parking, Wifi, YouTubeTV, Refreshingly Cool AC, Plush Pillows, and a Cozy bed.

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 139 reviews

2/1 Oceanfront Apartment with Dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Guest favourite

Holiday home in Key Largo

4.99 out of 5 average rating, 185 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Guest favourite

Home in Marathon

5 out of 5 average rating, 22 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 106 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Guest favourite

Apartment in Key Largo

4.89 out of 5 average rating, 114 reviews

Waterfront Spacious Condo Key Largo #1, 10% Off 7+

Relax in this calm, stylish space. Spacious condo, fully renovated waterfront 2 bedroom / 2 bath condo with three queen beds, sleeps 6. Feel at home with the superb layout, central AC, full kitchen with stove, microwave, full size refrigerator, one clean set of pans, utensils, plates, cups and linens. Private large balcony terrace accessible from living room and bedroom, water cove views, wireless internet, living room TV, washer and dryer in the unit, two assigned parking spaces.

Superhost

Flat in Key Largo

4.92 out of 5 average rating, 256 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Superhost

Home in Tavernier

5 out of 5 average rating, 4 reviews

Waterfront Islamorada Pool Heated Home private

Waterfront 4/3 home on the absolute best Canal. Deep Water direct oceanside access. Heated Pool and Hottub. Bring your boat or rent one locally and spend your keys vacation in paradise. This home has a swimming pool ,pool table, King size beds, Wifi, Flat-screen Tvs, BBQ, screened porch , washer/dryer. Located near the best restaurants and shops. Access to Founders park, Plenty of parking. Extra Fee for Dock Usage Monroe County Business Permit # 138028