Vacation rentals with a kayak in Treasure Island

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Top-rated kayak rentals in Treasure Island

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Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 138 reviews

2BR: Intercoastal Views, 3 Min Walk to Beach

LUXURY AWAITS in this 2 BR/1 BA full kitchen condo with unobstructed PANORAMIC WATER VIEWS of the SPARKLING Intracoastal WATERWAY!! Just minutes to the Gulf of Mexico by BOAT or FOOT! Enjoy the SUNRISE off the PRIVATE DOCK or take a 3 minute walk to the beach to ENJOY BREATHTAKING SUNSETS!! The Intracoastal has many advantages including very calm water for: Fishing, Boating, Paddle Boarding, Kayaking, and More! We are also a 3 minute walk to pickleball, basketball, and a fenced in playground!

Guest favorite

Condo in Indian Shores

4.9 out of 5 average rating, 136 reviews

On the Beach "Little Peace of Heaven" Beach Condo

Spacious - Complete Renovation - Come see!! Our building is on an Island and on the beach! Our unit faces East or the Inter-coastal but the beach is just downstairs. Our 8 unit building is ‘On the beach. Downstairs we have a beautiful semi-private patio area surrounded by sea grape plants. We have a table and chairs, 16 beach chairs, kayaks and paddleboards, outside shower, gas grill, & a firepit for all to enjoy. Wonderful & quiet for families & couples. No smoking in the unit. No pets.

Top guest favorite

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

4.99 out of 5 average rating, 137 reviews

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

Top guest favorite

A serene lakeside view is framed by tall trees with a lush green lawn in the foreground. A kayak is seen gliding across the calm water, reflecting the surrounding trees and blue sky. A covered dock is visible on the left, adding to the tranquil scenery.

Barn in Odessa

4.98 out of 5 average rating, 113 reviews

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.

Superhost

The cabin is viewed from the water, featuring a stylish exterior and a spacious deck. A newly constructed dock extends over the calm canal waters, surrounded by lush greenery. A clear blue sky enhances the inviting natural setting.

Home in Tampa

4.77 out of 5 average rating, 266 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Cabin. One of the last true Old Florida neighborhoods in the area. Located near charming Oldsmar. This is a Saltwater Gulf canal, only a few houses down from open the open Gulf in Tampa Bay. Great for the outdoorsy vacationer. Brand new dock. 2 kayaks (individual rider) & 2 bicycles provided. Depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Central location to Tampa & beaches!

Top guest favorite

Villa in Largo

4.97 out of 5 average rating, 142 reviews

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.

Top guest favorite

Cottage in Tampa

4.97 out of 5 average rating, 222 reviews

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.

Guest favorite

A small shed is seen with kayaks resting on its side, alongside various outdoor equipment and tools stored against the wall. The structure is surrounded by grass and a wooden fence, offering a glimpse of trees in the background under a clear blue sky.

Home in St. Petersburg

4.88 out of 5 average rating, 137 reviews

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Top guest favorite

A lakeside cabin is nestled among tall trees and palm greenery, showcasing a cozy porch with white chairs. The calm water reflects the cabin's brown exterior and nearby foliage, enhancing the serene outdoor environment.

Farm stay in Odessa

4.98 out of 5 average rating, 330 reviews

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).

Guest favorite

A person paddle boards across calm waters, surrounded by residential homes. The light clouds in the sky suggest a serene atmosphere, while palm trees are seen in the background, contributing to the coastal scenery.

Condo in Indian Rocks Beach

4.96 out of 5 average rating, 124 reviews

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam king bed & secured safe.

Guest favorite

A beach path leads to soft, white sand and the turquoise waters of the Gulf. A blue bicycle rests against a wooden railing, surrounded by grassy dunes under a bright blue sky with scattered clouds.

Home in Pass-a-Grille Beach

4.81 out of 5 average rating, 177 reviews

Steps 2 Beach-Island Cottage w/king bd+2bike+parki

Welcome to the Seashell rental, a hidden gem on Pass-a-Grille Island in St. Pete Beach! Just steps from the beach and crystal-clear waters. Relax in our well-appointed space with a King bed, living room, full kitchen. smart TVs, a step-in shower, and dining nook. Indulge in indoor or outdoor dining on the garden patios. A BBQ grill, 2 beach chairs+ 2 bikes are yours to enjoy! Unwind after beaching, shelling, fishing. Experience Pass-a-Grille's charm with us!

Top guest favorite

Home in Oldsmar

5 out of 5 average rating, 145 reviews

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