Vacation rentals with a kayak in Florida

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Top-rated kayak rentals in Florida

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Top guest favorite

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

4.99 out of 5 average rating, 100 reviews

Getaway on the Waterway: Kayak, SUP, fish, relax!

Welcome to your peaceful Getaway on the Waterway right on the beautiful canal that connects Big and Little Lake Weir! Kick your feet up and wave at the boats going by as you grill or fish from the dock. Play a round of corn hole, hop on one of our paddleboards or kayaks for beautiful ride to either lake! Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, (they also offer sunset cruises and water taxi service to Eaton's Beach restaurant right from our dock!) RELAX and ENJOY!

Guest favorite

A bright, open living space features light-colored wood flooring and white walls. A spacious gray sectional sofa is positioned near a coffee table, and a large dining table with seating for eight can be seen in the background. Natural light flows in from large windows.

Home in Melbourne

4.98 out of 5 average rating, 184 reviews

New Waterfront Bungalow Retreat + Tropical Vibes

"The River Oak Bungalow" is a brand new 4BR/2.5BA exotic, lush, private estate nestled amongst winding oaks & palms directly on the Indian River Lagoon. Located in the Downtown Eau Gallie Arts District, only a short drive to the Beaches, FIT, USSSA, & MLB Airport. Bring your boat & enjoy a private 100' dock & riverfront sandbar recreation area, huge outdoor deck, spacious backyard, fire pit, tree climbs, paddle boards, and kayaks. Perfect for Family Gatherings, Celebrations, or a staycation!

Top guest favorite

Home in Cape Coral

4.99 out of 5 average rating, 227 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Top guest favorite

An aerial view captures the lakefront property, showcasing a sandy beach, a private boat house, and a wooden dock extending into the lake. Lush greenery surrounds the home, and kayaks are visible along the shoreline, highlighting the outdoor recreational opportunities available.

Home in Sebring

4.97 out of 5 average rating, 124 reviews

LakeFront Sunrise Cottage

Catch sunrises or fish at this 2/1 lakefront house with sandy beach and private boat house! This cheery cottage is perfect for sunrises with coffee or exploring beautiful Lake Sebring on kayaks (included with booking). Plenty of parking onsite (bring your boat trailer), you will love this oasis on the lake! We want your stay to be pleasant and carefree so we do not require our guests to do any dishes, laundry, or other cleaning when checking out. Our housekeeping crew will take care of you!

Top guest favorite

A serene lakeside view features vibrant pink flowers and lush greenery framing a hammock. The calm, clear waters of the private lake are visible in the background, with two kayaks resting on the shore, creating an inviting space for relaxation.

Cottage in Hawthorne

4.97 out of 5 average rating, 157 reviews

Modern Cottage on Private Spring Fed Lake

Nestled on a gorgeous spring-fed private lake in the woods, our charming cottage is your ideal retreat. Whether you're dreaming of peace and quiet, a romantic getaway, or fun with your kids, this is the place to be! Kayak around the serene lake as you witness breathtaking sunsets, take a dip in the cool water or simply unwind amidst the beautiful surroundings. As night falls, gather around a fire and gaze up at the many stars lighting the sky. Come and create many cherished memories ☀️

Guest favorite

A refreshing plunge pool is surrounded by a spacious patio, accented by lounge chairs and stylish seating. The newly constructed guest home features multiple outdoor levels with a spiral staircase, and lush greenery lines the perimeter, enhancing the inviting outdoor space.

Guesthouse in Cocoa Beach

4.96 out of 5 average rating, 314 reviews

The Cocoa Boho Rooftop Retreat

Thinking about your next vacation? Need to unwind? Want to take in ocean views while sipping mimosas on a rooftop patio? Say hello to Cocoa Boho. Brand-new, clean boho-chic with bright & open interiors, a year-round summer breeze and the sounds of the Atlantic. Cocoa Boho is a newly constructed guest home - 2min walk to public beach access, 1.5 miles away from Downtown. If you're booking your next girls trip, poolside retreat or theme park crowd beach escape, Cocoa Boho is that vibe.

Top guest favorite

Tiny home in Key Largo

4.97 out of 5 average rating, 148 reviews

Oasis2 in Key Largo With a million dollar view

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.

Top guest favorite

A screened-in pool area features a sparkling blue pool surrounded by a concrete deck. Lush greenery and palm trees are visible outside the enclosure, with views of the water enhancing the serene setting.

Home in Merritt Island

4.99 out of 5 average rating, 211 reviews

Waterfront Home with Pool and Private Dock

Unwind in this intercoastal waterfront paradise with breathtaking sunrise views over the Banana River. Spot turtles, dolphins & manatees from your private dock. Retreat into elegance with a sophisticated upscale split floor plan coastal home. 🏡 Close to Cocoa Beach, Port Canaveral & Kennedy Space Center. Disney & Orlando are 40 mins away. 🐠🚣‍♂️ Provided kayaks, fishing poles, beach chairs & pool toys. Send us a message about the ultimate getaway with your own private pool & dock!

Top guest favorite

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

4.93 out of 5 average rating, 353 reviews

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.

Top guest favorite

Tiny home in Orlando

4.96 out of 5 average rating, 309 reviews

Lake View from King Bed+Free Bikes+Kayaks+Espresso

Highly recommended❤️ FREE BIKES KAYAKS & PADDLE BOARDS…..and - Espresso Machine☕️ - Couple’s Rain Shower - Heated King Bed - Lake Views from Bed - Hammock in Garden - Grill+Utensils - FREE Bikes+Kayaks+Paddle Boards - Private Garden Yard Seating Wake up to epic lake views from your king bed. Sip strong Cuban espresso, then launch a kayak or paddle board into calm waters—or bike into one of three charming nearby towns: Winter Park, Baldwin Park, or Downtown Orlando.

Top guest favorite

A vibrant red kayak is docked at the private launch area, with steps leading up from the water to the screened lanai. The spacious cottage, with its large windows, features colorful decor and a playful sculpture. Lush trees frame the peaceful waterway.

Cottage in Spring Hill

5 out of 5 average rating, 143 reviews

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

Top guest favorite

The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.

Home in Milton

4.96 out of 5 average rating, 185 reviews

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.