Holiday rentals with a kayak in Dunedin

4.96 out of 5 average rating, 109 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 Barrington Hills

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. Happy holidays from our family to yours

4.98 out of 5 average rating, 164 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

4.97 out of 5 average rating, 157 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, 249 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.

4.75 out of 5 average rating, 161 reviews

Condo in Ruskin

Little Harbor Resort #109 Tampa Bay FL Beach, Pool

Little Harbor Resort is a paradise packed with amenities. Enjoy 2 pools, Jacuzzi, Beach on Tampa Bay (not Gulf), 2 restaurants, Tiki Bar, tennis, pickleball, basketball, playground, fishing charters, sightseeing cruises, and Freedom Boat Club. The Inn at Little Harbor River Delight Studio is a ground-floor, non-smoking studio which features a kitchenette, fridge, microwave, sink, in counter hotplate, dishwasher, coffee maker with two luxurious queen beds, and captivating island decor.

4.95 out of 5 average rating, 148 reviews

Home in Apollo Beach

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

4.99 out of 5 average rating, 338 reviews

A spacious cabin is gently illuminated by string lights, creating a warm glow against the evening sky. Surrounding the home are trees and a hammock, with a grassy area leading up to the porch where seating is visible.

Farm stay in Odessa

Farm and lake stay at Maison de L'eau Douce

LAKEHOUSE PRIVATE cabin-farmhouse décor-full kitchen/living room-cozy bedroom/full bath-W/D- 2.5 acres-2 flat screen TVs with Roku (Netflix, Spectrum cable app, and more)-bamboo hard wood flooring- high thread count sheets-very comfy queen bed. IKEA Sleeper sofa in livingroom. Kitchen: gas range-dishwasher-microwave-Keurig machine. Wooded setting-large deck with views of the lake. WIFI. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Condo in Independence Square

The open-concept living area features a modern kitchen with stainless steel appliances and a granite countertop. A seating area includes a light gray sofa adorned with blue and pink pillows, and a wooden coffee table. Natural light fills the space through shuttered windows, enhancing the homey feel.

4.94 out of 5 average rating, 216 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.

4.99 out of 5 average rating, 571 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

4.91 out of 5 average rating, 151 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 and experience the tranquility of country living!

4.96 out of 5 average rating, 118 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 beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

5 out of 5 average rating, 154 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

Popular amenities for Dunedin kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.88 out of 5 average rating, 153 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

4.72 out of 5 average rating, 171 reviews

The image showcases a heated in-ground pool bordered by light-colored pavers, overlooking a calm canal. Docked boats and palm trees line the water's edge, reflecting under a clear blue sky. The well-kept lawn adds a touch of green to the serene waterside setting.

Home in New Port Richey

Gulf Harbors Getaway Home with Pool

4.95 out of 5 average rating, 57 reviews

Adirondack chairs are arranged on a pebbled area facing a tranquil canal, with a sunset casting a warm glow over the scene. The serene water reflects the colorful sky, surrounded by lush greenery and residential homes lining the opposite bank.

Home in Forest Hills

Holiday fun canal home

4.99 out of 5 average rating, 86 reviews

A patio area is visible featuring a round table with chairs, surrounded by decorative plants. Kayaks are propped against the railing, while the shimmering water of the canal flows in the background, framed by palm trees and bright blue skies.

Home in Holiday

Nature Lovers Retreat

4.98 out of 5 average rating, 113 reviews

A serene waterfront view captures a canal lined with homes and docks. The still water reflects the soft hues of the sunset, while palm trees and boats add to the tranquil atmosphere.

Home in Bay Crest Park

Canal views, weekly and monthly Discounts

4.88 out of 5 average rating, 102 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, 132 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

Home in Indian Rocks Beach

4.96 out of 5 average rating, 128 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

Cottages with a kayak

Cottage in St. Pete 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, 302 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Clearwater Beach

4.78 out of 5 average rating, 162 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Cottage in St. Pete Beach

4.89 out of 5 average rating, 184 reviews

Steps2Beach-Walk everywhere-Bikes & gear Included

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

4.79 out of 5 average rating, 127 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

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

5 out of 5 average rating, 4 reviews

Riverfront Home w/ Putting Green & Boat Dock!

4.89 out of 5 average rating, 37 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

A bright living area is furnished with a comfortable sectional sofa and a circular coffee table atop a textured rug. A flat-screen TV is positioned on a light-colored console. Natural light filters in through a large window with wooden blinds, creating a welcoming atmosphere.

Cottage in Port Richey

Nature, Comfort, and Calm – All on the Bayou

Other holiday rentals with a kayak

Home in Indian Rocks Beach

A spacious waterfront home is showcased with a pool and lounging area. The outdoor space features comfortable seating arrangements and a patio alongside the water. The second level balcony overlooks the backyard, enhancing the setting with a relaxed vibe.

5 out of 5 average rating, 8 reviews

Amazing Waterfront Home 2BLKS 2 Beach & Restraunts

4.94 out of 5 average rating, 89 reviews

A serene view of Tampa Bay is showcased, featuring calm waters reflecting a soft sky. Two private docks, one at an angle, provide access to the water, framed by distant greenery along the horizon.

Home in Ruskin

Silverking Keys Retreat!

Home in Indian Rocks Beach

A private pool is featured, with a sun shelf and loungers positioned alongside it. Two large umbrellas provide shade over the loungers. The calm waterfront is visible in the background, framed by palm trees and dock structures.

5 out of 5 average rating, 21 reviews

WTFR home heated pool, golf cart, kayaks, SUP

Condo in Indian Rocks Beach

4.94 out of 5 average rating, 47 reviews

Beach Villa 2 Bedroom. *Updated Kitchen & Bath*

4.88 out of 5 average rating, 17 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, 80 reviews

A bright living area is shown, featuring a comfort-focused seating arrangement with soft, light-colored furniture. A large TV occupies one wall, and the kitchen area is visible in the background, showcasing updated appliances and a light, airy design.

Home in Palm Harbor

Charming Coastal Home Near Top Beaches

4.96 out of 5 average rating, 68 reviews

A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.

Home in Forest Hills

*NEW* Riverside Retreat w/Pool