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Waterfront vacation rentals in Islamorada

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Top-rated waterfront rentals in Islamorada

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

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Top guest favorite

A shaded dock area featuring a thatched roof provides a comfortable seating space with a long picnic table overlooking calm waters. Bright colors are seen on signage around the perimeter, adding a lively touch to the serene water view.

Condo in Key Largo

4.99 out of 5 average rating, 110 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.

A turquoise picnic table is set with an assortment of snacks, including chips and shells, complemented by a vase with a branch. Nearby, a pitcher of water and a bottle are visible. The serene waterfront is framed by palm leaves and a distant boat.

Camper/RV in Key Largo

4.96 out of 5 average rating, 115 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 that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

A light-filled living area features a cozy white sofa adorned with decorative pillows. A glass coffee table sits atop a soft area rug, while a large window offers a view of the outside. A decorative woven chair and potted plants enhance the inviting ambiance.

Vacation home in Key Largo

4.93 out of 5 average rating, 117 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.

The image captures a serene waterfront scene, featuring a calm canal lined with palm trees and modern residences. A concrete dock with a set of metal steps leads down to the water, reflecting the clear blue sky.

Apartment in Key Largo

4.83 out of 5 average rating, 252 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.

A comfortable living area is presented, featuring a black leather sofa and a natural wood coffee table. A flat-screen TV is mounted on the wall, with light drapes framing the sliding glass doors that open to a scenic waterfront view.

Apartment in Key Largo

4.93 out of 5 average rating, 156 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

Top guest favorite

A private porch overlooks the tranquil harbor, featuring blue chairs beside a white railing. A boat is secured at the dock, with sailboats moored in the distance. Bright sunlight reflects off the water's surface, creating a serene atmosphere.

Vacation home in Key Largo

4.99 out of 5 average rating, 200 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

Aerial view of a waterfront property featuring a covered outdoor seating area, surrounded by palm trees and tropical landscaping. The dock extends into the water, with a buoy visible nearby. Gravel pathways lead to the home, which has a light blue exterior.

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Home in Key Colony Beach

4.95 out of 5 average rating, 112 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.

Condo in Key Largo

4.9 out of 5 average rating, 126 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.

An aerial view captures the serene landscape of Manatee Bay, showcasing lush green mangroves surrounding calm waters. A boat marina is visible, with a collection of boats anchored, while several buildings are scattered along the waterfront, providing a glimpse of the local community.

Apartment in Key Largo

4.92 out of 5 average rating, 264 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!

Home in Marathon

4.89 out of 5 average rating, 160 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Islamorada waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

Apartment in Key Colony Beach

4.84 out of 5 average rating, 109 reviews

Beachside Unit 22 - Private Beach on Atlantic

Top guest favorite

A wooden dive platform extends into the saltwater lagoon, featuring a ladder for easy access. Lush greenery surrounds the area, contributing to a serene atmosphere, while the sunlight reflects off the water's surface, creating a calm and inviting setting.

Apartment in Key Largo

4.99 out of 5 average rating, 145 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

A cozy outdoor seating area is depicted, featuring two wicker chairs with light blue cushions and a small black table. A wooden bench is positioned against the wall, enhancing the conversational space. Sliding glass doors provide access to the interior.

Apartment in Key Largo

5 out of 5 average rating, 52 reviews

Key Largo, Florida - Gem by the Sea

A serene waterfront view showcases two multi-story buildings with balconies, surrounded by palm trees. A boat is docked at the marina alongside wooden posts, reflecting the calm turquoise water under a clear blue sky.

Apartment in Marathon

5 out of 5 average rating, 18 reviews

#1 Island Hideaway 89 - OCEAN FRONT

A light-filled living area showcases large glass doors that open to a scenic ocean view. Comfortable seating is arranged around a round dining table, highlighted by a surfboard resting nearby. The decor reflects a casual coastal style, enhancing the relaxing atmosphere.

Apartment in Key Largo

4.79 out of 5 average rating, 145 reviews

Escape to the Seaside!

Top guest favorite

Apartment in Marathon

5 out of 5 average rating, 5 reviews

Ocean Side Paradise Awaits!

A bright living space features a sign labeled 'BEACH HOUSE' above a large sliding door that opens to ocean views. Soft natural-colored curtains frame the doorway, and a cozy chair sits next to a woven basket, enhancing the room’s serene ambiance.

Apartment in Tavernier

4.95 out of 5 average rating, 193 reviews

Boho FL Keys Condo

A deck area is shown with a gray patio table and four metal chairs. Two blue lounge chairs are positioned nearby, overlooking the sandy beach. The calm sea stretches in the background, complemented by a clear sky and lush greenery along the shoreline.

Apartment in Marathon

4.97 out of 5 average rating, 104 reviews

Beachfront Condo w/ Ocean Views in Marathon

Waterfront house rentals

A private pool and jacuzzi are surrounded by a grassy area, with colorful lounge chairs positioned nearby. The view captures the serene waterway and neighboring properties under a bright sky, offering a peaceful outdoor setting.

Home in Marathon

4.83 out of 5 average rating, 24 reviews

Dock Pool Ramp Jacuzzi Ocean Views Kayaks

Aerial view of the oceanfront condo complex, showcasing its three levels and vibrant coral roof. The lush landscaping complements the structure, with palm trees lining the property. The tranquil waters reflect the surrounding greenery and provide access to boat slips underneath the building.

Home in Islamorada

5 out of 5 average rating, 6 reviews

A Pirates Great Escape ~ 3bed/2baths Ocean View B

A canal-side view of the duplex showcases a wooden dock with ladder access to the water. The exterior features large windows and an awning, while palm trees frame the bright blue structure, creating a relaxed coastal atmosphere.

Home in Key Colony Beach

4.91 out of 5 average rating, 135 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

Home in Marathon

5 out of 5 average rating, 3 reviews

Paradise Palms~ Open Water Views w/ 40' Dock, Pool

An aerial view showcases a two-story beach house with a gray metal roof, surrounded by lush palm trees and well-maintained landscaping. A private dock is visible alongside the house, providing access to a wide canal, with additional homes and greenspace in the background.

Home in Key Colony Beach

5 out of 5 average rating, 26 reviews

Easy Ocean Access 30' Dock House Pool Cabana Club

A serene bayfront area is viewed, featuring a wooden dock leading to calm water surrounded by lush coconut palms. Steps descend into the water, inviting exploration. The bright sky and gentle sunlight create a peaceful atmosphere, emphasizing the natural beauty of the waterfront setting.

Home in Key Largo

4.9 out of 5 average rating, 105 reviews

Sunsets In Palms Paradise

A sandy beach area features swaying palm trees and a thatched gazebo providing shade. In the background, colorful kayaks and paddle boards are visible along the shoreline, while calm waters reflect the blue sky dotted with fluffy clouds.

Home in Key Largo

4.83 out of 5 average rating, 60 reviews

Deckhouse

Top guest favorite

A sandy beach is lined with lounge chairs under tall palm trees, facing a calm turquoise sea. A pier extends into the water, and a few beachgoers are sunbathing on the shore. The sky is partly cloudy, providing a serene atmosphere.

Home in Key Colony Beach

4.98 out of 5 average rating, 104 reviews

Waterfront House with 37 ft Dock & Cabana Club

Waterfront condo rentals

Condo in Marathon

5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

Condo in Tavernier

4.87 out of 5 average rating, 150 reviews

Reel Large END Unit in Ocean Point Suites

Condo in Key Largo

4.87 out of 5 average rating, 121 reviews

Kawama Breeze

A serene dock extends into the calm water, surrounded by lush greenery. The wooden planks, bathed in sunlight, lead to a small bay. A white bird stands perched at the edge, adding a touch of wildlife to the tranquil scene.

Condo in Tavernier

4.94 out of 5 average rating, 140 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Top guest favorite

A modern waterfront building is situated near a calm marina, surrounded by palm trees. The structure features multiple large windows and a bright blue roof. A concrete ramp leads down to the water, where boats are docked, creating a serene atmosphere.

Condo in Tavernier

4.98 out of 5 average rating, 196 reviews

Ocean Views at Ocean Pointe

Condo in Tavernier

4.99 out of 5 average rating, 106 reviews

Modern and Coastal Ocean Pointe 2307

Condo in Tavernier

4.84 out of 5 average rating, 152 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

Top guest favorite

Condo in Marathon

4.96 out of 5 average rating, 100 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Quick stats about waterfront rentals in Islamorada

Total rentals
480 properties
Nightly prices starting at
G$14,629 GYD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
340 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with a pool
340 properties have a pool

Destinations to explore