
Holiday rentals with a kayak in Clearwater Beach
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Clearwater Beach
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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!

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.

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

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.

A little piece of Heaven
2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

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.

Tampa Bay Gem - Spectacular Beachfront Views
Escape to the tranquil shores of Rocky Point Island and bask in the awe-inspiring beauty of the ocean view. Our impeccable condo boasts stunning sunsets over Tampa Bay, perfect for a stylish getaway. Just steps away from Ben T Davis Beach and delicious restaurants, plus the Tampa Int'l Airport, Raymond James Stadium, downtown, Amalie Arena, Straz Center, Historic Ybor City, Hyde Park, Soho, Riverwalk, and the Port of Tampa. Book now for an unforgettable experience filled with adventure.

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.

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).

Breathtaking Beachy Houseboat on Clearwater Island
🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴♂️🏄♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤 NO PETS ALLOWED.

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.
Popular amenities for Clearwater Beach kayak rentals
Holiday House Rentals with a Kayak

Waterfront | King Bds | Htd Pool | BBQ | 2 Kayaks

Azule|Waterfront | Walk to Beach-Dock-Bikes-Kayaks

Peaceful Pet friendly 2 BR cottage with hot tub.

Fabulous Beach House 3BR, SPACIOUS, Beach breezes!

Cambria Beach House Clearwater Beach

Backyard Oasis on The Cove Near Indian Rocks Beach

Lake Tarpon Waterfront-Private

St Pete Luxe TreeTop Beach Home
Cottages with a kayak

Sunny PaG Island rental w/bikes-just steps2beach

Pink Gulfside Cottage, Steps to Beach, Pets OK

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Little Manatee River Cottage

Sleep 7 Steps to Beach Pets OK Real Beach Cottage

Happy Camper Cottage | Cozy Oasis with Hot Tub

Alafia River Cottage

Elegant Crystal Beach cottage within sea glimpse
Other holiday rentals with a kayak

Nautical Landings West-Honeymoon Island!

Beautiful Tampa Pool/ Hot Tub Home- Spacious Yard

Flamingo Flair & Waterfront Air — Pure Paradise!

Riverfront Hideaway Near Downtown

Waterfront Oasis! Kayaks,Hot Tub

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Private Guest Suite w/Water View, Pool &Hot Tub

Pirate’s Cove
Quick stats about holiday rentals with a kayak in Clearwater Beach

Total holiday rentals
Explore 30 holiday rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach holiday rentals start at $123 AUD per night before taxes and fees

Verified guest reviews
Over 2,900 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Clearwater Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Clearwater Beach rentals

4.8 Average rating
Clearwater Beach stays are highly rated by guests—averaging 4.8 out of 5!
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- Anna Maria Island
- Weeki Wachee Springs
- John's Pass
- Raymond James Stadium
- Dunedin Beach
- Busch Gardens Tampa Bay
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Lido Key Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Gulfport Beach Recreation Area
- Jannus Live
- ZooTampa at Lowry Park
- North Beach
- Adventure Island
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Splash Harbour Water Park
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Busch Gardens