Vacation rentals with a kayak in Palm Harbor

5.0 out of 5 average rating, 101 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

Outdoor spacesLocationBiking

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!

🌴 Escape to this luxurious waterfront retreat in the peaceful community of Tampa Shores ☀️ an outdoor lover’s dream with direct bay access to the Intracoastal. Enjoy fishing, dolphin 🐬and manatee 🌿🦭 watching, or simply relax on your private dock surrounded by nature. Start your morning with coffee ☕️ on the second-story screened patio, offering breathtaking canal views and overlooking the heated private swimming 🏊‍♀️ pool below. The possibilities are endless! Lay back and enjoy your stay!

LocationValueBiking

4.98 out of 5 average rating, 106 reviews

A wooden deck is set up with tall bar stools around a circular table, surrounded by tropical plants. Palm fronds provide shade, while the open space creates a relaxed outdoor dining area. The vibrant green lawn enhances the tropical atmosphere.

Home in Port Richey

Waterfront home w/dock-Kayaks & Jon Boat included!

Escape to this charming two-bedroom waterfront duplex, complete with a floating dock offering direct access to the Gulf of Mexico. Spend your days exploring the area's picturesque mangroves and scenic waterways using the provided battery-powered Jon boat or kayaks. Step outside to a backyard that feels like your own tropical retreat. A surround-sound music system extends throughout the property, creating the perfect atmosphere for entertaining, lounging, or simply soaking in the vacation vibes

Outdoor spacesValueWifi

4.96 out of 5 average rating, 134 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

ValueOutdoor spacesFamily

4.96 out of 5 average rating, 204 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

Outdoor spacesValueCondition

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!

Outdoor spacesLocationKitchen

4.99 out of 5 average rating, 106 reviews

A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.

Guesthouse in Westchase

Cottage in Paradise.

Relax and unwind at our 2 bedroom, 1.5 bath, GUEST HOUSE (ONLY). Enjoy the pool, Beautifully landscaped grounds with Koi pond & mini golf. See birds, butterflies and more in our 1 acre botanical gardens. Free use of Golf Cart. Kayaks are available (with transport fee. I live in the main house and I'm happy to ensure that you have everything you need for an amazing vacation, while still giving you plenty of privacy. Check in & out times are not set & very flexible for your convenience.

ValueOutdoor spacesPool

4.98 out of 5 average rating, 173 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.

ValueLocationHospitality

4.97 out of 5 average rating, 117 reviews

Home in Hudson

45% OFF- Pet friendly, waterfront, kayaks, fishing

• Private boat dock & floating dock – Bring your boat and keep it secured in the water! • Kayaks included – Explore the scenic canals and nearby waterways. • Tiki hut – Kick back in the shade with a cool drink. • Fenced in backyard - Paved and fenced in backyard. • Fishing right from the backyard – Cast a line and see what you can catch! • Spacious outdoor seating – Enjoy sunset views and coastal breezes. • Immediate access to the Gulf of Mexico - A short boat ride away.

LocationValueCondition

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.

5.0 out of 5 average rating, 107 reviews

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.

ValueOutdoor spacesSolo travel

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.

4.9 out of 5 average rating, 174 reviews

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.

LocationValueSleep quality

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.

ValueLocationCheck-in

Popular amenities for Palm Harbor kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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

LocationValueBathroom

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

LocationValueAir conditioning

4.95 out of 5 average rating, 104 reviews

Home in New Port Richey

Hidden Treasure @ Treasure Island NPR, RV friendly

ValueLocationBackyard

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.

5.0 out of 5 average rating, 48 reviews

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Outdoor spacesLocationBiking

5.0 out of 5 average rating, 47 reviews

Home in Crystal Beach

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

ValueOutdoor spacesBeach

An aerial view of a spacious backyard featuring a heated swimming pool surrounded by lush greenery. A seating area with comfortable chairs and an umbrella provides shade, while a paved patio adds to the outdoor space. The area is enclosed by tall white fencing for privacy.

5.0 out of 5 average rating, 34 reviews

Pool home minutes from the beach.

Outdoor spacesLocationPool

4.95 out of 5 average rating, 57 reviews

Pirate’s Cove

LocationOutdoor spacesGrill

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.

5.0 out of 5 average rating, 86 reviews

Charming Coastal Home Near Top Beaches

Outdoor spacesLocationComfort

Cottage rentals with a kayak

4.98 out of 5 average rating, 269 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

ValueLocationLong stay

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

ValueLocationComfort

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

LocationOutdoor spacesLaundry

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

4.9 out of 5 average rating, 40 reviews

Coastal cottage within sea glimpse

LocationGetting aroundNearby

Superhost

A large, partially covered deck offers a view of the canal, accented by palm trees and a clear blue sky. Outdoor seating areas include a wooden rocking chair and several dining chairs, inviting relaxation by the water's edge.

Cottage in Hudson

4.86 out of 5 average rating, 21 reviews

Water Front Nautical Haven

LocationOutdoor spacesBiking

Superhost

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.

Cottage in Tarpon Springs

Seaside Cottage- Gulf Waterfront with heated pool

LocationParksComfort

4.86 out of 5 average rating, 159 reviews

A welcoming porch is framed by light blue walls and features a table with two chairs. A round mirror hangs on the wall, and a decorative lantern is attached beside the entrance. A set of steps leads down to the front yard.

Cottage in Hudson

My Happy Place!

LocationValueFamily

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

4.7 out of 5 average rating, 156 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

Outdoor spacesLocationCheckout

Other vacation rentals with a kayak

Bungalow in Tarpon Springs

The exterior of a charming house is presented, featuring a welcoming porch with two potted plants. A large tree provides shade, and the facade showcases a blend of orange shingles and gray walls. Steps lead up to the entrance, enhancing the inviting appearance.

4.93 out of 5 average rating, 71 reviews

Hibiscus Hideaway

Outdoor spacesLocationBeach

A modern kitchen showcases sleek cabinetry and a spacious island with seating for four. Stainless steel appliances are complemented by a blue tile backsplash. Natural light fills the area through skylights and large windows, highlighting the contemporary design and inviting atmosphere.

4.93 out of 5 average rating, 76 reviews

Tranquil Fully Renovated Modern Home Palm Harbor

LocationOutdoor spacesView

4.94 out of 5 average rating, 31 reviews

A tranquil view features a swimming pool set against a stunning sunset over the water. The horizon glows with warm orange and yellow hues, while the reflection dances on the calm surface. Lush green grass surrounds the pool area, enhancing the serene atmosphere.

Apartment in Palm Harbor

Amazing Gulf front Sunsets from private apartment

Outdoor spacesLocationKitchen

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.

4.83 out of 5 average rating, 29 reviews

Boat house on the gulf 4B/3B

LocationOutdoor spacesSleep quality

4.95 out of 5 average rating, 85 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 Holiday

*NEW* Riverside Retreat w/Pool

ValueLocationQuiet

5.0 out of 5 average rating, 32 reviews

Best Family Vacation at the Beach or the Pool.

LocationSleep qualityPool

A cozy front porch is shown, featuring two white seated chairs and a glass table on a patterned rug. Decorative welcome signage and lighting are present, along with potted plants that enhance the welcoming atmosphere.

4.94 out of 5 average rating, 52 reviews

Lake Tarpon Waterfront-Private. Spend Labor Day !

LocationOutdoor spacesCheck-in