Vacation rentals with a kayak in Dunedin

5.0 out of 5 average rating, 102 reviews

Guesthouse in Clearwater

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

4.96 out of 5 average rating, 135 reviews

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

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

4.96 out of 5 average rating, 205 reviews

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

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

4.96 out of 5 average rating, 111 reviews

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

Paradise!Renovated waterfront pool home.Sunsets!

Sunsets to die for! Remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard & and spotting 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. Fishing rods.Bonfire pit.Grill.Heated pool for a fee. Portable crib,stroller, high chair. Come,relax&enjoy No hurricane damage!

Apartment in Clearwater Beach

Clearwater Coastal Condo | Walk to beach + Bikes!

Ultimate Waterfront Escape – Stay and Play Clearwater Beach! Welcome to your beach home away from home! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard straight out of your backyard, then cruise around town on our complimentary beach bikes. Jet ski island tours, Boat Charters, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories!

4.87 out of 5 average rating, 186 reviews

4.97 out of 5 average rating, 174 reviews

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

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.

Condo in Indian Rocks Beach

An aerial view captures the Aqua Beach Condo location, highlighting proximity to both the Intracoastal Waterway and the beach. Lush greenery and the vibrant blue waters contrast with the nearby buildings, while the sandy shoreline stretches along the coast under a clear sky.

Steps from the Sand - Clean, Stylish 2-BR Condo

AQUA BEACH CONDO - Only 90 steps from the beach, this beautifully updated and perfectly located beach condo offers you the very best of Indian Rocks Beach, a charming and intimate beach town located between Clearwater and St. Pete Beach. Two bedrooms with en-suite bathrooms and large walk-in closets, as well as the lofty living area and modern open kitchen will make you feel like at home. This condo is better equipped than your average vacation rental. Continue to read for more...

4.95 out of 5 average rating, 232 reviews

A spacious living area features a large sectional sofa, complemented by decorative tables and potted plants. Expansive windows provide views of the water and outdoor seating, while natural light brightens the modern, open layout.

5.0 out of 5 average rating, 100 reviews

Walk to Beach! Waterfront Lux Retreat w/Kayaks

As seen on the Emmy award-winning show, Staycation. Experience the serene beauty of a waterfront Indian Rocks Beach Home. Wake up to breathtaking views of the water, right from your window. Enjoy the luxury of kayaking or fishing off your private boat dock. Spend evenings gathered around the fire pit or showcase your culinary skills with our grill. Just a 7-minute walk and you'll find yourself on the pristine white sands of Indian Rocks Beach. Kayaks and boat lift available.

Apartment in Tarpon Springs

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.

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.

5.0 out of 5 average rating, 107 reviews

4.89 out of 5 average rating, 165 reviews

Luxury waterfront | Walk to beach • Private dock

Welcome to Villa Azule, a spacious luxury waterfront retreat where the beach and boating lifestyle come together. Walk to Indian Rocks Beach in about 10 minutes, then return to your private waterfront setting with a dock, boat, and WaveRunner lifts. This 4-bedroom home sleeps up to 10 and includes complimentary kayaks, bikes, fishing and beach gear. With generous indoor-outdoor living and beautiful water views, Villa Azule is made for an unforgettable Florida getaway.

4.9 out of 5 average rating, 176 reviews

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

Peaceful Pet friendly 2 BR cottage with hot tub.

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.

4.96 out of 5 average rating, 135 reviews

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

Home in Dunedin

Heated saltwater pool|Spacious 4BR/3BA|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches.

Popular amenities for Dunedin kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.97 out of 5 average rating, 145 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

4.93 out of 5 average rating, 152 reviews

A screened-in patio features a heated swimming pool, surrounded by white decking. The pool offers a view of the canal with palm trees and neighboring properties beyond. The tranquil outdoor space is complemented by a backyard with swings and a dock visible in the background.

Home in Town 'n' Country

Waterfront Resort with HEATED POOL!

4.83 out of 5 average rating, 136 reviews

A spacious pool area features a heated saltwater pool and a hot tub surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a grill is visible, providing an inviting outdoor space. The screened enclosure offers a sense of privacy and comfort.

Home in Belleair Bluffs

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

4.93 out of 5 average rating, 102 reviews

Salty Air Retreat - Hot Tub | Walk to the Beach!

4.92 out of 5 average rating, 122 reviews

An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.

Home in Holiday

Lakefront Paradise with Heated Saltwater Pool

4.88 out of 5 average rating, 104 reviews

Home in Holiday

Family Coastal Home w/ EV Charger, Bikes &Kayaks

4.92 out of 5 average rating, 171 reviews

A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.

Home in Tampa

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

5.0 out of 5 average rating, 48 reviews

A wooden dock stretches over calm water, framed by white railings. One black Adirondack chair is positioned to enjoy views of the water and distant shoreline against a backdrop of a pastel sky at dusk.

Home in Palm Harbor

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Cottage rentals with a kayak

4.98 out of 5 average rating, 270 reviews

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

Bay Lake Cottage, Private Dock, Romantic, Fishing

4.97 out of 5 average rating, 145 reviews

A serene lakefront view is framed by tall trees draped with Spanish moss. A wooden dock extends into the calm water, providing a space for relaxation. Soft shadows are cast across the lush green lawn, inviting guests to enjoy the peaceful surroundings.

Cottage in Lutz

A little piece of Heaven

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

4.89 out of 5 average rating, 193 reviews

4.96 out of 5 average rating, 73 reviews

The exterior of a bright green cottage is framed by lush greenery and ornamental plants. A welcoming porch features seating arrangements, and hanging flower baskets add a touch of vibrancy. Sunlight filters through the trees, creating a cheerful and inviting entrance.

Cottage in Crystal Beach

Escondido Boutique Bungalow in Crystal Beach

4.9 out of 5 average rating, 40 reviews

A cozy outdoor space is framed by lush greenery and bamboo, containing several chairs arranged around a circular table. A BBQ grill is positioned against the exterior wall of the cottage, and colorful inflatables are placed nearby, creating a relaxed environment.

Cottage in Crystal Beach

Coastal cottage within sea glimpse

Cottage in Tarpon Springs

An aerial view showcases the peninsula of Seabreeze Island, surrounded by tranquil blue waters. The landscape is dotted with homes and docks, with greenery visible in the background. The horizon presents a soft gradient of colors as the sun sets, creating a peaceful atmosphere.

Seaside Cottage- Gulf Waterfront with heated pool

A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.

Cottage in Crystal Beach

Happy Camper Cottage | Cozy Oasis with Hot Tub

4.67 out of 5 average rating, 159 reviews

A comfortable living area features light-colored leather seating arranged around a softly textured rug. Natural light fills the space through large windows, complemented by a ceiling fan and neutral wall tones. A dining area and kitchen are visible in the background.

Cottage in Port Richey

Riverfront Home w/ Putting Green & Boat Dock!

5.0 out of 5 average rating, 5 reviews

Other vacation rentals with a kayak

4.83 out of 5 average rating, 64 reviews

A light-filled living area features a comfortable leather sofa, a glass coffee table, and a stylish armchair. A large painting adds color to the wall, while sliding glass doors overlook greenery. A dining table with chairs is visible through the opening.

Apartment in Ozona

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona

4.62 out of 5 average rating, 26 reviews

Apartment in Dunedin

Sunset Studio Retreat | Beso Del Sol Dunedin

4.96 out of 5 average rating, 54 reviews

Home in Clearwater

Escape, explore, tranquility, frappé

4.96 out of 5 average rating, 54 reviews

A private saltwater pool is framed by a paved patio, featuring two lounge chairs positioned for relaxation. Surrounding greenery offers a sense of seclusion, while a white privacy fence delineates the outdoor space. The home is partially visible in the foreground.

Home in Palm Harbor

Affordable Family Escape w/ Saltwater Pool

5.0 out of 5 average rating, 13 reviews

Home in Clearwater

Calumet by the Creek | Free kayaks & bikes | 8 pp

Townhouse in Clearwater Beach

A swimming pool is surrounded by white lounge chairs, set against a tranquil waterfront. Lush palm trees are visible, with docks and boats visible in the background. The clear blue sky reflects off the water, creating a serene outdoor space.

Waterfront Penthouse Rooftop Casita 5-min to Beach

4.88 out of 5 average rating, 33 reviews

4.83 out of 5 average rating, 29 reviews

An aerial view captures a stunning waterfront landscape, with lush green areas framing the calm waters. The covered boat dock is visible at the forefront, providing access to various water activities, while neighboring homes and boats dot the shoreline under a bright blue sky.

Home in Tarpon Springs

Boat house on the gulf 4B/3B