Holiday rentals with a kayak in Clearwater Beach

Guest house 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

5.0 out of 5 average rating, 102 reviews

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

4.83 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

Enjoy best of Florida in this Updated and Newly Furnished 4 bed, 3 bath with PRIVATE SCREENED HEATED SALT WATER POOL and HOT TUB + FLORIDA ROOM+ GAME ROOM located short 3 miles to the beach. This home is in the quiet neighborhood, close to shopping, restaurants, grocery shops and beach. House accommodates up to 10 guests and has 1 KING BED and 3 QUEEN BEDS and 1 Bunk Bed for sleeping arrangements Both Living room and Florida room have Large Sectional Sofas Grill is available in the backyard

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.

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

You’ll have the Entire 500sq ft Cottage & private entry, deck and fishing dock, charcoal grill, 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 drapes, luxury quality hair products, high thread count linens. Fully stocked kitchen, reverse osmosis drinking water, k-cup/drip coffee machine. The lake has bass, complimentary fishing poles/tackle box. Rentable Canoe & Kayaks.

Apartment 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

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.

4.85 out of 5 average rating, 158 reviews

Flat in Clearwater Beach

Waterfront Escape | Steps to Clearwater Beach

Ultimate Waterfront Escape – Adventure Awaits! 🏄‍♂️ + Pet Friendly! Welcome to the "Lily Pad" Unit! Your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on our kayaks or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Check out our Island Dolphin Jet ski tours that leave right from our campus + on-site offices for local recommendations!

4.93 out of 5 average rating, 102 reviews

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

🌊 Salty Air Retreat | Walk to Indian Rocks Beach | Hot Tub + Kayak & Paddle Board ~ Managed by Sandy Feet Vacation Rentals Welcome to Salty Air Retreat, a spacious and family-friendly Indian Rocks Beach vacation home just a short walk from the Gulf Coast’s beautiful white sand beaches! Enjoy the best of Florida beach living with a private backyard, hot tub, beach gear, kayak, paddle board, and a location close to restaurants, parks, and attractions.

Bungalow in Indian Rocks Beach

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.

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

4.97 out of 5 average rating, 234 reviews

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

Enjoy this South Tampa waterfront pool home, centrally located off Westshore. Close proximity to Clearwater, downtown Tampa, and Orlando. Featuring brand new contemporary finishes and breathtaking views. This home Is monitored on video surveillance on the exterior corners of the home as well as the back yard and front door ring camera. Device will record during reservations. No parties of any kind will be permitted.

Apartment in St. Petersburg

An inviting balcony view overlooks a spacious pool area and the intercoastal waters, framed by palm trees. A light-filled living area features comfortable furnishings and a television, while the dining space and kitchen are visible, providing a warm atmosphere for relaxation and enjoyment.

Breathtaking Waterview & Pool View Condo

Waterfront condo with pool view. The view of the intercoastal is fantastic. Especially beautiful sunsets! Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking intercoastal or stay indoors and enjoy puzzles and games.

4.86 out of 5 average rating, 335 reviews

Popular amenities for kayak rentals in Clearwater Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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|

4.91 out of 5 average rating, 190 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

4.93 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!

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, 199 reviews

Piece of paradise in Indian Rocks Beach.

4.86 out of 5 average rating, 118 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, Bikes-Kayaks-SUP

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

5.0 out of 5 average rating, 48 reviews

Home in Crystal Beach

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

5.0 out of 5 average rating, 71 reviews

Aerial view of the property highlights a private dock with a kayak, surrounded by lush tropical landscaping. A tiki dining hut is situated on the spacious lawn, providing a serene outdoor space. The waterway can be seen flowing alongside the home, enhancing the natural setting.

Home in Largo

Largo Waterfront Oasis: Pool, Dock, Manatees

Cottage rentals with a kayak

Superhost

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.

Cottage in Pass-a-Grille Beach

Sunny PaG Island rental w/bikes-just steps2beach

4.81 out of 5 average rating, 316 reviews

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

4.9 out of 5 average rating, 152 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

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

Superhost

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

4.9 out of 5 average rating, 40 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

4.69 out of 5 average rating, 158 reviews

Cottage in Ruskin

1839 2 Bedroom

A serene view of a calm body of water is captured at dusk, with the moon reflecting softly on the surface. Lush greenery, including palm trees, is visible along the shoreline, creating a tranquil natural backdrop.

Cottage in Ruskin

Amazing on river cottage with dock to fish, kayak!

Other holiday rentals with a kayak

Apartment in Indian Shores

A spacious living area features a comfortable brown sectional sofa adorned with patterned cushions. A round coffee table sits at the center. Natural light fills the room through large glass doors leading to a balcony. A cozy hanging chair and a dining area with bar stools are visible in the background.

Beautiful boho 2br townhome- pool, walk to beach!

4.92 out of 5 average rating, 127 reviews

Superhost

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

Dolphin Cove Waterfront St. Pete Beach w/ Pool

4.76 out of 5 average rating, 217 reviews

4.87 out of 5 average rating, 15 reviews

Flat in Indian Shores

Beachfront Island Studio · Walk to Sand #5

Apartment in Indian Shores

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.

Oceanfront · Steps to Sand · Free Kayaks

4.99 out of 5 average rating, 86 reviews

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

5.0 out of 5 average rating, 54 reviews

Flat in Indian Shores

Spacious Beach Condo - Mariner's Pointe

Apartment in Indian Rocks Beach

2BR/2BA WFRT Condo with Dock near beach #3

4.96 out of 5 average rating, 24 reviews