Vacation rentals with a kayak in Clearwater Beach

4.95 out of 5 average rating, 188 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

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, 102 reviews

Waterfront studio great for Pasco scallop season!

Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size bed and pullout sofa. 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.

4.96 out of 5 average rating, 100 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!

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

4.98 out of 5 average rating, 168 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.

5 out of 5 average rating, 127 reviews

Guest suite in Largo

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks

Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

4.98 out of 5 average rating, 263 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.

4.91 out of 5 average rating, 162 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.

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.

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.

4.95 out of 5 average rating, 223 reviews

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...

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.

4.98 out of 5 average rating, 601 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

4.96 out of 5 average rating, 134 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

Apartment in Clearwater Beach

A living area features a comfortable blue sofa and a wooden coffee table. A round dining table with four chairs is positioned nearby. Large windows offer natural light and a view of the outdoors, while a ceiling fan adds to the room's functionality.

4.88 out of 5 average rating, 155 reviews

Beachy Bayfront Condo Walk 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—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

Apartment in Indian Rocks Beach

5 out of 5 average rating, 110 reviews

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

☀ Bay View Duplex ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music

Popular amenities for Clearwater Beach kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.89 out of 5 average rating, 171 reviews

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

Home in St. Petersburg

Hibernate in our Bear Creek Home

4.89 out of 5 average rating, 160 reviews

Azule|Waterfront | Walk to Beach-Dock-Bikes-Kayaks

4.92 out of 5 average rating, 136 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

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

4.99 out of 5 average rating, 193 reviews

Piece of paradise in Indian Rocks Beach.

5 out of 5 average rating, 9 reviews

Beach in 90 Seconds w/ Hot Tub, Coffee Bar & Games

4.99 out of 5 average rating, 106 reviews

Beach, golf cart, pool and pickleball at Oasis

4.94 out of 5 average rating, 160 reviews

Home in Apollo Beach

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

4.94 out of 5 average rating, 247 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

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

An inviting dining space displays a wooden table paired with white chairs, complementing light blue walls. A small sideboard houses essentials, while natural light streams through a large window. The open layout connects to a cozy living area with a television and tasteful decor.

4.81 out of 5 average rating, 309 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Clearwater Beach

4.77 out of 5 average rating, 168 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Cottage in Pass-a-Grille Beach

4.89 out of 5 average rating, 188 reviews

Steps2Beach-Walk everywhere-Bikes & gear Included

4.9 out of 5 average rating, 147 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

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

4.72 out of 5 average rating, 139 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

4.94 out of 5 average rating, 98 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

Cocos Cottage Cottage-Summer fun! 10%off 6/1-8/30

4.9 out of 5 average rating, 39 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

Elegant Crystal Beach 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

Other vacation rentals with a kayak

4.88 out of 5 average rating, 122 reviews

A sunlit dock area features several wooden chairs positioned under a large blue canopy. Water stretches out into the distance, dotted with small islands under a clear blue sky. The calm waves create a serene atmosphere.

Condo in Dunedin

Nautical Landings West-Honeymoon Island!

A four-person outdoor dining table is set with plates and glasses of red wine, overlooking the waterway. A double kayak is visible on the shore, and boats are docked in the background under a blue sky with a few clouds.

4.92 out of 5 average rating, 79 reviews

Waterfront | King Bds | Htd Pool | BBQ | 2 Kayaks

5 out of 5 average rating, 71 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

Summer Sale Ocean Front | Stunning Views | HGTV

5 out of 5 average rating, 11 reviews

Home in Indian Shores

Walks on the Shores • Private Beach Front Access

Apartment in Indian Shores

5 out of 5 average rating, 4 reviews

Gulf-to-Bay Island Apt · Steps to Beach #1

5 out of 5 average rating, 8 reviews

Harbor Haven: Heated Pool Home w/ Golf Cart

4.96 out of 5 average rating, 23 reviews

Home in Redington Shores

Billy's Beach Bungalow