Holiday rentals with a kayak in Tarpon Springs

4.98 out of 5 average rating, 103 reviews

A warm glow from a fire pit illuminates the backyard, surrounded by lush greenery and palm trees. A deck adorned with string lights can be seen in the background, under a night sky featuring soft clouds and a bright moon.

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

LocationOutdoor spacesParking

4.96 out of 5 average rating, 130 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

LocationValueAccuracy

4.95 out of 5 average rating, 197 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 spacesLocationAmenities

4.99 out of 5 average rating, 159 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.

ValueOutdoor spacesView

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.

4.96 out of 5 average rating, 108 reviews

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

ValueOutdoor spacesView

4.91 out of 5 average rating, 170 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.

ValueLocationGetting around

4.99 out of 5 average rating, 350 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).

Outdoor spacesLocationComfort

4.96 out of 5 average rating, 111 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.

LocationOutdoor spacesCleanliness

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, 618 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, pond, fire pit, hammocks, greenhouse, and we even have rabbits! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

LocationOutdoor spacesBackyard

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, 106 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.

LocationOutdoor spacesParking

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.

4.94 out of 5 average rating, 251 reviews

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.

ValueLocationBiking

5 out of 5 average rating, 169 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

ValueOutdoor spacesAccess

Popular amenities for Tarpon Springs kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.99 out of 5 average rating, 101 reviews

The outdoor area is illuminated by soft lighting, showcasing a spacious lawn with lounge chairs and a red umbrella. The cozy patio area features seating, creating an inviting space for relaxation. A small dog is seen enjoying the yard, adding a touch of life to the scene.

Home in Hudson

Angele's House, Waterfront with direct Gulf access

LocationValueDecor

5 out of 5 average rating, 12 reviews

Anclote River House Retreat

LocationNearbyComfort

5 out of 5 average rating, 131 reviews

The kitchen features light turquoise walls and dark wood cabinetry. Open shelving displays dishware and decorative items. A stainless steel stove and microwave are installed, with a large sink beneath a window. Counter space is available for meal preparation and dining.

Home in Hudson

Rachel's Place

LocationOutdoor spacesView

5 out of 5 average rating, 30 reviews

Best Family Vacation at the Beach or the Pool.

LocationWalkabilityNearby

A serene lake view is captured at sunset, with soft colors reflecting on the water's surface. Lush greenery borders the edge, framing the scene and creating a peaceful atmosphere. The silhouettes of trees are visible against the evening sky, enhancing the tranquil setting.

4.88 out of 5 average rating, 48 reviews

Cozy Beach Home w/Lake view and Kayak!

LocationOutdoor spacesFamily

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.

4.95 out of 5 average rating, 82 reviews

*NEW* Riverside Retreat w/Pool

ValueOutdoor spacesCheckout

A charming coastal home is set among greenery, featuring a well-kept front yard with various plants and trees. A paved driveway leads to the entrance, which includes a door framed by decorative green shutters. Natural sunlight enhances the inviting atmosphere.

4.96 out of 5 average rating, 45 reviews

Tarpon Springs Beach Bungalow

Outdoor spacesLocationCondition

5 out of 5 average rating, 25 reviews

Waterfront Experience | Boatlift & Boat Rental

LocationOutdoor spacesParks

Cottages with a kayak

Cottage in Clearwater Beach

4.77 out of 5 average rating, 172 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

Outdoor spacesValueQuiet

4.95 out of 5 average rating, 20 reviews

Cottage in Aripeka

Aripeka Island Retreat Driftwood Cottage

LocationOutdoor spacesBathroom

4.98 out of 5 average rating, 267 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

ValueLocationAccess

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

4.71 out of 5 average rating, 150 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

LocationValueAmenities

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, 5 reviews

Riverfront Home w/ Putting Green & Boat Dock!

LocationOutdoor spacesHospitality

4.86 out of 5 average rating, 21 reviews

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

Water Front Nautical Haven

Outdoor spacesLocationKitchen

4.9 out of 5 average rating, 40 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

LocationAccuracyFamily

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 holiday 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, 69 reviews

Hibiscus Hideaway

Outdoor spacesValueBeach

4.97 out of 5 average rating, 39 reviews

Waterfront Escape, H/Pool, Boat Dock, Gulf Access

Outdoor spacesLocationBarbecue

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.

4.99 out of 5 average rating, 91 reviews

Nature Lovers Retreat

Outdoor spacesLocationHospitality

4.99 out of 5 average rating, 77 reviews

A serene waterfront view is presented with calm waters reflecting a clear blue sky. Two kayaks in vibrant green and blue are positioned along the shore, while multiple boats are docked nearby. A neatly arranged stone path leads towards the water, surrounded by green grass and landscaping.

Home in New Port Richey

Beautiful Home with a Pontoon!

ValueLocationQuiet

4.97 out of 5 average rating, 78 reviews

A spacious living area is furnished with two comfortable sofas and a coffee table, complemented by a decorative rug. Artwork featuring seashells adorns the walls, and a large television provides entertainment. Natural light flows through the numerous windows, enhancing the open atmosphere.

Home in New Port Richey

Waterfront Getaway w/ Dock & Kayaks – Dog Friendly

Outdoor spacesLocationGetting around

A screened-in green room features two wooden chairs positioned around a small table, surrounded by various indoor plants. Natural light streams through the slatted roof, illuminating the view of the river visible through the openings in the walls.

4.83 out of 5 average rating, 93 reviews

Riverside Home with Kayaks

Outdoor spacesLocationTV

5 out of 5 average rating, 5 reviews

Lake House w/ Kayaks, Fishing & Heated Comm Pool

Outdoor spacesLocationCondition