Vacation rentals with a kayak in Clearwater

Condo in Indian Rocks Beach

A well-maintained outdoor area features a putting green surrounded by lush green turf. Comfortable lounge chairs are positioned nearby, with a table and chairs set against a backdrop of the Intracoastal waterway. A clear blue sky and vibrant foliage contribute to the serene atmosphere.

4.79 out of 5 average rating, 139 reviews

2BR: Intercoastal Views, 3 Min Walk to Beach

LUXURY AWAITS in this 2 BR/1 BA full kitchen condo with unobstructed PANORAMIC WATER VIEWS of the SPARKLING Intracoastal WATERWAY!! Just minutes to the Gulf of Mexico by BOAT or FOOT! Enjoy the SUNRISE off the PRIVATE DOCK or take a 3 minute walk to the beach to ENJOY BREATHTAKING SUNSETS!! The Intracoastal has many advantages including very calm water for: Fishing, Boating, Paddle Boarding, Kayaking, and More! We are also a 3 minute walk to pickleball, basketball, and a fenced in playground!

4.99 out of 5 average rating, 143 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

4.8 out of 5 average rating, 318 reviews

A tranquil outdoor space features a private pool surrounded by lush greenery and lounge chairs. The vibrant sunset casts pink and orange hues over the water, with a boat docked in the background. Potted plants add a touch of nature to the serene setting.

Guest suite in Riverbend

The Riverfront Suite at Casa del Alma

The riverfront suite @ Casa Del Soul has something for everyone. Whether you’re traveling for business, on vacation exploring Tampa Bay, or wanting to get out of the house for a weekend stay-cation look no more. Casa del Soul is centrally located in trendy/ eclectic neighborhood of Seminole Heights just minutes away from Ybor, Hard Rock, Downtown, South Tampa, Hyde Park , Lowry Park Zoo, Busch Gardens, Adventure Island, the Amphitheater, Arena, International Mall, Stadium, Restaurants & More.

4.98 out of 5 average rating, 120 reviews

The exterior of a newly constructed barn loft apartment is shown, featuring a wraparound deck accessed by wooden stairs. Beneath the deck, picnic tables and seating areas are visible among the surrounding greenery and trees. The property is set in a spacious outdoor environment.

Barn in Odessa

Cypress Lakes Barn Retreat

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

4.97 out of 5 average rating, 145 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.

4.97 out of 5 average rating, 228 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

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.

Tiny home in Ybor City Historic District

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

4.99 out of 5 average rating, 536 reviews

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

4.94 out of 5 average rating, 233 reviews

The exterior of a two-story home is featured, set in a lush, green environment near a tranquil lagoon. Tall trees and hanging moss frame the structure, which is elevated slightly above the water. The calm water reflects the house and surrounding foliage.

Home in Tarpon Springs

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

Guesthouse in South Seminole Heights

4.87 out of 5 average rating, 947 reviews

Seminole Heights Riverside Paradise w/Pool

Whether you're traveling for business, seeking a FL adventure or a short getaway staycation, the stunning waterfront views, pool & incredible amenities with convenient proximity to downtown Tampa, airport & area attractions, the guesthouse at Isla de Dij is the perfect accommodation. You'll fall in love with the massive live oaks that line the brick paved streets, the glassy waters of the Hillsborough River and the brilliant sunsets that paint the evening sky.

4.98 out of 5 average rating, 188 reviews

A spacious backyard is highlighted by a hammock suspended between two trees, inviting relaxation. A black dog and a tan dog can be seen exploring the grassy area, surrounded by tall trees adorned with Spanish moss. A guesthouse is visible in the background.

Farm stay in Odessa

Farm and lake stay at Malfini Cay

PRIVATE GUESTHOUSE...Lakefront -full kitchen living room-very large bedroom-full bath-2.5 acres. Newly decorated/remodeled. 2 flat screen TVs-Roku (Netflix and Spectrum app)-WIFI -laminate flooring-high thread count sheets-comfy queen bed. IKEA sleeper sofa in livingroom. All kitchen appliances with coffee bar/Keurig-W/D. Wooded setting-beautiful views of ski lake. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

5 out of 5 average rating, 146 reviews

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

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

Vacation home in Clearwater Beach

A living area features a navy blue sofa and wooden coffee table, with a decorative fish wall art and plants adding a coastal touch. A television is situated on a sleek white console. Light wood flooring enhances the spacious feel, complemented by a welcoming 'Welcome' sign.

4.87 out of 5 average rating, 156 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

🌊 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. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

Popular amenities for Clearwater kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.91 out of 5 average rating, 137 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.

4.88 out of 5 average rating, 100 reviews

Aerial view of a beach with soft white sand and turquoise waters, showcasing several beachgoers relaxing under the sun. Residential buildings are visible in the background, indicating a serene coastal community. The shoreline curves gently, inviting exploration and enjoyment of the beach.

Home in Indian Shores

Fabulous Beach House 3BR, SPACIOUS, Beach breezes!

4.92 out of 5 average rating, 124 reviews

A view of the beach is captured through swaying palm trees, framed by a white picket fence. Nearby, a pathway leads to the sand, while parked cars line the road. The clear blue sky complements the vibrant coastal scenery.

Home in Clearwater Beach

Cambria Beach House Clearwater Beach

4.91 out of 5 average rating, 192 reviews

A serene outdoor space is featured, showcasing a circular arrangement of Adirondack chairs surrounding a fire pit. Soft string lights illuminate the area, with a hammock positioned nearby. The backdrop includes the water, a boat dock, and trees under a colorful sunset sky.

Home in Tampa

Luxurious "Riverfront Oasis" - Waterfront w/pool

Home in Indian Rocks Beach

5 out of 5 average rating, 41 reviews

Dolphin Blue Beach House-Waterfront, Pet friendly

Home in Indian Rocks Beach

A waterfront view showcases a heated pool and hot tub, surrounded by smooth white tiles. Lush green plants frame the area, while the calm water reflects the blue sky. The Belleair Bridge can be seen in the distance, enhancing the scenic landscape.

5 out of 5 average rating, 23 reviews

New Waterfront house pool hot tub golf cart kayaks

4.85 out of 5 average rating, 550 reviews

A well-appointed bathroom features a freestanding soaking tub surrounded by natural stone walls. A double vanity with modern fixtures is situated near the window, allowing for natural light. A glass-enclosed shower and stylish fixtures enhance the functional layout.

Home in Tampa

Urban River Edge Loft w/Soaking Tub and King Bed

5 out of 5 average rating, 4 reviews

Home in Seminole

5BR~Heated Pool~Private Retreat~Bike to Beach!

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.

4.8 out of 5 average rating, 291 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Clearwater Beach

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

4.78 out of 5 average rating, 157 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

4.91 out of 5 average rating, 125 reviews

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

Little Manatee River Cottage

Cottage in Clearwater Beach

A charming pink cottage displays a welcoming façade with colorful accents. Outdoor seating areas are present, including a swing and bicycles parked nearby. The property is surrounded by lush greenery, enhancing its beachside appeal and inviting relaxation.

4.66 out of 5 average rating, 158 reviews

Sleep 7 Steps to Beach Pets OK Real Beach Cottage

4.84 out of 5 average rating, 107 reviews

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

4.93 out of 5 average rating, 87 reviews

A cozy living space features a dark leather couch and a decorative wooden coffee table. Natural light streams through large windows adorned with blue patterned curtains. A flat-screen TV is mounted on the wall, and a wooden cabinet displays nautical-themed decor.

Cottage in Riverview

Alafia River Cottage

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

4.89 out of 5 average rating, 36 reviews

Elegant Crystal Beach cottage within sea glimpse

Two comfortable chairs with light cushions are positioned under a large umbrella on a wooden deck. Lush greenery, including palm trees and shrubs, surrounds the area, creating a serene outdoor space with ample natural light.

Cottage in Indian Rocks Beach

1 Bd Immaculate Gulf front BOHO Beach Cottage

Other vacation rentals with a kayak

5 out of 5 average rating, 47 reviews

The image showcases a serene beach scene framed by lush green trees. Soft sand meets gentle waves under a bright blue sky. Vibrant coastal vegetation leads to the sandy shoreline, where silhouettes of beachgoers can be seen in the distance, enjoying the tranquil setting.

Condo in Indian Shores

Stylish Beachfront Condo, Stunning Views

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.

5 out of 5 average rating, 85 reviews

Waterfront studio w/Hot Tub and Putting Green

4.98 out of 5 average rating, 47 reviews

A cozy living area showcases a blue sofa paired with a decorative pillow and a wooden coffee table. Sliding glass doors lead to a bedroom. A wall-mounted television is positioned above an electric fireplace, contributing to a comfortable setting.

Guesthouse in Odessa

Breathtaking Lakefront Glass Cottage

5 out of 5 average rating, 15 reviews

A decorative mermaid statue is positioned beside a small table set with two wine glasses and a bottle, overlooking the river. The outdoor decking features a mix of wood and stone materials, while lush greenery is visible in the background under a bright blue sky.

Guest suite in Ruskin

The little house!

5 out of 5 average rating, 10 reviews

A clear swimming pool rests within a screened enclosure, surrounded by tropical greenery. Comfortable lounge chairs are positioned by the water's edge, inviting relaxation. The pool features a connected hot tub, offering options for leisure and enjoyment.

Villa in Wimauma

Coastal Farmhouse & Pool

5 out of 5 average rating, 8 reviews

Condo in Indian Shores

Peaceful Penthouse Escape | Oceanfront View & Pool

5 out of 5 average rating, 10 reviews

An aerial view captures the canalfront property, showcasing the large pool and spa surrounded by tropical landscaping. The private dock accommodates a boat, while a beach area is visible with lounge chairs and palm trees enhancing the waterfront setting.

Home in Apollo Beach

*New* Waterfront Retreat: Pool, Spa, Dock & Views