
Holiday rentals with a kayak in Hillsborough County
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Hillsborough County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Private Island Old FL Waterfront Heaven on Earth
Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

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

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.

Cheerful Country Home 5 min Amphitheater/Fairgroun
We are back to Market! Ask how to get 10% night rate discount!!! Bring the whole family to our great home. Spacious house to relax and have fun. Perfect location central to all Tampa attractions. 2 miles to Hard Rock Casino, MidFlorida Amphitheatre, & Florida Fairgrounds. 10 min to Bush Gardens, Adventure Island, Tampa Riverwalk and Ybor City. Enjoy a peaceful country feel and safe neighborhood. Tampa Bay beaches are minutes away, 45 min to Clearwater and St. Pete. 55 miles to Disneyworld.

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.

River Oasis w/ Swim Spa & Hoop Court walk to Zoo
Stay in this spacious 3 bed 2.5 bath 2-story home right across from the Hillsborough River and mins from Lowry Park Zoo & natural springs. Perfect for families or groups wood floors, large family room w/ fireplace. Stainless steel appliances fully stocked kitchen art deco cabinets, this home is as stylish as it is comfortable offering a one-of-a-kind stay. Step outside to enjoy a 24-foot heated swim spa, your own painted half-court basketball court, and a fenced backyard for total privacy

Luxurious "Riverfront Oasis" - Waterfront w/pool
Luxurious, riverfront home with a coastal-farmhouse design, creating the ultimate Florida getaway or staycation! Spend your vacation relaxing in our private heated, waterfall pool, around the fire pit, or dining on the lit up boat dock. Beautifully furnished and professionally designed with lots of additional amenities, including bathrobes, aromatherapy diffusers, TWO fully stocked kitchens, bluetooth speaker, fishing poles and more! Plus, spectacular views of the Downtown Tampa Skyline!

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.

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.

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

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

Ocean Dreaming: Waterfront Home with Heated Pool,
Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.
Popular amenities for kayak rentals in Hillsborough County
House rentals with a kayak

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

Lux Mid-Century Downtown Courtyard+Parking

Bayside Retreat your tropical oasis

Casa Coquina: waterfront, pool, hot tub, boat lift

Luxury Waterfront Oasis With Heated Pool (option)

Amazing Experience Imperial Key - Tampa FL

Waterfront Mid - Century Modern Cottage

Silverking Keys Retreat!
Cottage rentals with a kayak

Little Manatee River Cottage

A little piece of Heaven

Cocos Cottage Summer fun! 10% off 6/1-8/31, 2026

Sunny PaG Island rental w/bikes-just steps2beach

Serene Island Cottage Waterfront Haven

Escondido Boutique Bungalow in Crystal Beach

Coastal cottage within sea glimpse

Seaside Cottage- Gulf Waterfront with heated pool
Other holiday rentals with a kayak

Cypress Lakes Barn Retreat

Lakeside Villa

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

The '59 Flamingo | Pool, Hot Tub & Cold Plunge

Waterfront Condo with Boat Slip & Fishing Dock

*New* Waterfront Retreat: Pool, Spa, Dock & Views

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Lakefront Pool Retreat • Kayaks • 8 Miles to Beach
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- Rentals with a kayak Florida
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Reunion Resort Golf Courses - Palmer & Watson
- Bean Point Beach
- Amalie Arena
- Hard Rock Casino
- LEGOLAND Florida Resort
- University of South Florida
- Dunedin Beach
- ChampionsGate Golf Club
- Vinoy Park
- Epperson Lagoon
- John's Pass
- Tropicana Field
- Southern Dunes Golf and Country Club
- Island H2O Live!
- MidFlorida Credit Union Amphitheatre
- Weeki Wachee Springs State Park
- Sand Key Beach
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