Vacation rentals with a kayak in Clearwater Beach Island

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Top-rated kayak rentals in Clearwater Beach Island

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

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Top guest favorite

Guesthouse in Clearwater

5 out of 5 average rating, 100 reviews

Charming Casita Near Two Downtowns & Beaches

This charming casita is a guest house located walking distance to downtown Dunedin, the Blue Jay's stadium, and short distance to downtown Clearwater and Clearwater beach. Steps to walking along the intracoastal for a walk or bike ride on the Pinellas trail. Conveniently acccessable to anything you may need for your stay. There is no shortage of things to do; shopping, water sports, fishing, biking, local parks, museums, cruises, etc.. Lots of variety for during the day and for night life. I’m

Outdoor spacesValueQuiet

Top guest favorite

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

4.96 out of 5 average rating, 130 reviews

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

LocationValueKitchen

Guest favorite

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

4.95 out of 5 average rating, 196 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

LocationValueHiking

Top guest favorite

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

4.96 out of 5 average rating, 108 reviews

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

LocationValueGetting around

Top guest favorite

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

Villa in Largo

4.98 out of 5 average rating, 172 reviews

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

ValueOutdoor spacesAir conditioning

Top guest favorite

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

4.98 out of 5 average rating, 267 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

LocationValueParking

Guest favorite

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

Home in Palm Harbor

4.91 out of 5 average rating, 169 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today! Please note that the minimum age requirement to book is 23.

LocationValueNearby

Top guest favorite

An aerial view showcases a modern two-story house surrounded by water and greenery. A private boat dock is positioned in the foreground, along with a manicured lawn featuring a putting green and colorful kayaks. Solar panels are visible on the rooftop.

Apartment in Tarpon Springs

5 out of 5 average rating, 106 reviews

Waterfront Studio Apartment w/access to Gulf

Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size. Microwave, coffee maker, stove top, refrigerator/freezer, 62" Smart TV, gas BBQ. Hot tub (only available from Oct 1st-May 31st) Enjoy the sun, beautiful nature of Anclote River with 3 kayaks and 3 paddle boards. Daily sightings of dolphins, manatees and many species of birds passing by. Fish right off the sea wall. Beach is a short 2-miles away. Overnight boat docking.

LocationValueBiking

Superhost

Large sliding glass doors open to waterfront views, revealing a sunlit space with a modern kitchenette. A small dining table with two chairs is set near the doors, and a flat-screen TV is mounted on the wall, complementing the serene aquatic surroundings.

Houseboat in Clearwater

4.78 out of 5 average rating, 136 reviews

Breathtaking Beachy Houseboat on Clearwater Island

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

Outdoor spacesLocationFamily

Top guest favorite

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Bungalow in Indian Rocks Beach

4.97 out of 5 average rating, 230 reviews

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

ValueLocationCondition

Guest favorite

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

4.78 out of 5 average rating, 209 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Outdoor spacesValueParks

Top guest favorite

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

5 out of 5 average rating, 169 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

LocationValueDecor