Vacation rentals with a kayak in Tarpon Springs

4.99 out of 5 average rating, 136 reviews

Home in Hernando Beach

Firepit, Golf Cart, Kayaks, Pedal Boat, Fishing!

Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard. Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River — perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!!

Home in Sea Ranch on the Gulf

The exterior of a freshly redone home is visible, featuring a combination of yellow siding and stone accents. A welcoming sign is positioned near the entrance, surrounded by colorful flower beds with various blooms and maintained landscaping, creating an inviting approach to the property.

4.86 out of 5 average rating, 123 reviews

Waterfront house near Gulf of Mexico

Freshly redone home that is yours to enjoy. 2 bedrooms and 2 bathrooms that can accommodate 4 guests. Enjoy the gorgeous sunsets from either the screened-in back porch or the dock on the canal. Or, jump into the kayak and paddle a very short distance (7 houses down the canal) to the Gulf of Mexico. Fishing tackle and poles are available. Friendly, quiet neighborhood that is great for walking or riding the bikes that are included with the house. Plenty of restaurants or shopping nearby.

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

4.99 out of 5 average rating, 137 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.

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, 95 reviews

Waterfront studio w/Hot Tub and Putting Green

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.

4.83 out of 5 average rating, 109 reviews

A view of the private dock features wooden posts and a boat lift, with calm water reflecting the surrounding waterfront homes. The scene captures a mix of greenery and colorful buildings in the background, under a cloudy sky that hints at a serene atmosphere.

Home in Hudson

Hudson Beach waterfront house, boat lift, Tiki Hut

**NO CLEANING or PET FEES** Visit is limited to registered guests. List price is for 1 guest: $25/ea additional guest per day (regardless of overnight) with a 6 person limit. Enjoy beautiful canals & manatees/dolphins from the spacious tiki hut. Put your boat on our lift or rent from marina down the street; launch one or all of our 3 kayaks or bring yours; fish from the dock. Walk to: 3 seafood restaurants with live music, Hudson Beach, Robert J. Strickland Park, Skeleton Key Marina

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).

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, 572 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!

4.94 out of 5 average rating, 240 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

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.

4.99 out of 5 average rating, 158 reviews

An aerial view showcases the property nestled among lush greenery along the Alafia River. A spacious yard is bordered by trees, and a covered pool area is visible. The river reflects the surrounding landscape, contributing to the tranquil setting of the retreat.

Guest suite in Riverview

The Guest House at Riverbend Retreat Fla.

True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.

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

Popular amenities for Tarpon Springs kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 51 reviews

A spacious heated pool area is surrounded by a screened enclosure, featuring clear blue water under bright sunlight. A view of the waterfront is visible beyond the pool, with palm trees and homes reflected in the water. Potted plants add a touch of greenery.

Home in Hudson

Beautiful sunsets, waterfront 2/2 pool home

4.95 out of 5 average rating, 59 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

4.98 out of 5 average rating, 83 reviews

Home in Hudson

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

4.98 out of 5 average rating, 42 reviews

The exterior of a waterfront home is visible, featuring a white dock and a boat lift. A spacious lawn with palm trees is situated in front of the house, while colorful decorations are draped across the dock. Clear blue skies reflect in the calm water.

Home in Port Richey

Blue Marina House

5 out of 5 average rating, 32 reviews

The exterior of the home features a welcoming entrance and landscaped yard, showcasing vibrant tropical plants and a decorative pathway. An inviting pool area includes seating along the deck, with loungers arranged for comfort. Scenic water views are visible from a nearby deck, with kayaks ready for use.

Home in Holiday

Gulf Access, Heated Pool, Near Islands, Beaches

4.9 out of 5 average rating, 80 reviews

Home in Holiday

Family Coastal Home w/ EV Charger, Bikes &Kayaks

5 out of 5 average rating, 14 reviews

Two orange kayaks are positioned on the grassy bank near calm waters, ready for exploration. A dock with steps leads down to the water, surrounded by lush greenery. Clear blue skies add to the inviting atmosphere for a day of paddling.

Home in Holiday

Lakeside Escape w/ Kayaks, Firepit & BBQ!

5 out of 5 average rating, 126 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 Sea Pines

Rachel's Place

Cottage rentals with a kayak

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

4.9 out of 5 average rating, 141 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

4.98 out of 5 average rating, 250 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

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

4.77 out of 5 average rating, 128 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, 5 reviews

Riverfront Home w/ Putting Green & Boat Dock!

4.89 out of 5 average rating, 19 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

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

Other vacation rentals with a kayak

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

Home in Sea Ranch on the Gulf

At night, a cozy firepit is surrounded by lush palm trees, providing a serene atmosphere. Soft lighting highlights the adjacent outdoor space of the home, where comfortable seating is arranged, creating an inviting spot for relaxation by the water.

4.87 out of 5 average rating, 70 reviews

SunWild Ventures Home *Golf Cart & Kayaks*

4.99 out of 5 average rating, 69 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!

4.93 out of 5 average rating, 30 reviews

A serene view of the Anclote River at sunrise, with a coffee cup placed on the dock's edge. The sun is seen rising above the water, reflecting golden hues on the surface. Lush trees frame the scene, creating a peaceful atmosphere.

Home in Forest Hills

Anclote Oasis-Sunsets-Pool-Kayak-Fish-Gulf Access

4.94 out of 5 average rating, 35 reviews

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.

Home in Palm Harbor

Lake Tarpon Waterfront-Private

Home in Indian Rocks Beach

A tranquil waterfront view is captured during sunset, featuring a heated pool and spacious hot tub. Surrounding palm trees add a touch of greenery, while the Belleair Bridge is visible in the distance against a colorful sky reflected in the water.

5 out of 5 average rating, 27 reviews

New Waterfront house pool hot tub golf cart kayaks

4.96 out of 5 average rating, 47 reviews

An aerial view reveals a spacious residential area with waterfront properties, showcasing a variety of rooftops and well-maintained yards. The nearby canals and waterways are visible, along with the open Gulf of Mexico in the distance, illustrating the community's scenic and accessible location.

Home in New Port Richey

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