Vacation rentals with a kayak in Florida Keys

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Top-rated kayak rentals in Florida Keys

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

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Guest favorite

A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.

Townhouse in Key Largo

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

LocationValueCleanliness

4.87 out of 5 average rating, 182 reviews

Guest favorite

Home in Marathon

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

ValueOutdoor spacesGrill

4.93 out of 5 average rating, 82 reviews

Guest favorite

A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.

Home in Key Largo

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

LocationOutdoor spacesLayout

4.91 out of 5 average rating, 208 reviews

Guest favorite

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

ValueOutdoor spacesAccess

4.96 out of 5 average rating, 213 reviews

Guest favorite

A floating home is anchored in clear waters, surrounded by lush greenery. The structure is highlighted by solar panels on the roof and a spacious white deck, featuring railings that outline the edges. Bright blue skies and distant mangroves create a serene backdrop.

Houseboat in Islamorada

Perfect escape to the ocean

Enjoy the sounds of nature when you stay in this unique place. What awaits you is fun filled days living and exploring out on the fabulous florida keys waters in your own private floating paradise that is completely solar powered and all the amenities run 24/7! This fabulous floating home was build in 2025 and very nice, update and comfortable, it is 100% solar powered and eco friendly All the amenities run off batteries and solar power so you'll be able to enjoy cold ac, fridge, tv , 24/7

ValueLocationSleep quality

4.79 out of 5 average rating, 68 reviews

Top guest favorite

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

My Little Oasis2 Waterfront Retreat, Key Largo

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

LocationOutdoor spacesHeating

4.97 out of 5 average rating, 237 reviews

Top guest favorite

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

Beach House | Waterfront Villa | Kayaks

Wake up to beautiful water views and the laid-back charm of Duck Key. This beautifully renovated waterfront villa offers a relaxed coastal setting, comfortable living spaces, and inviting outdoor areas made for morning coffee, sunset views, and evening cocktails. Ideally located in the heart of the Florida Keys, it’s a perfect home base for boating, fishing, snorkeling, beach days, and waterfront dining, with Marathon, Key West, Islamorada, and other Keys favorites within easy reach.

LocationOutdoor spacesAmenities

4.96 out of 5 average rating, 193 reviews

Top guest favorite

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Outdoor spacesValueBreakfast

4.93 out of 5 average rating, 394 reviews

Top guest favorite

Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

LocationCleanlinessNearby

5.0 out of 5 average rating, 6 reviews

Top guest favorite

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

b watervibe

Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales. Toda una experiencia de camping para los huéspedes que les gusta lo divertido y diferente. Prueben y ustedes dirán. Ofrece un espacio para 2 personas .

ValueOutdoor spacesWalkability

4.93 out of 5 average rating, 101 reviews

Guest favorite

A waterfront patio is shown with comfortable seating, overlooking a calm body of water. The sun sets in the distance, casting warm light over the scene. Tropical vegetation can be seen, adding to the serene atmosphere.

Home in Key Largo

The Paradise 2

Relax with the whole family at this peaceful place to stay. Our home is located right by the water. Modern spacious and spotless with private parking, fast Wi-Fi, cold AC plus cozy beds and pillows in every bed. Relax on the waterfront patio chairs, swim in our newly renovated pool, go kayaking out in the bay, watch the manatees and dolphins swim by and go fishing from our backyard dock anytime. We are sure you will absolutely love our Tiny Home!

Outdoor spacesLocationBathroom

4.9 out of 5 average rating, 175 reviews

Superhost

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

*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.

ValueLocationBathroom

4.88 out of 5 average rating, 137 reviews