
Holiday rentals with a kayak in Clearwater
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Clearwater

Total holiday rentals
Explore 70 holiday rentals in Clearwater

Nightly prices starting at
Clearwater holiday rentals start at $69 NZD per night before taxes and fees

Verified guest reviews
Over 5,170 verified reviews to help you choose

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Clearwater holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Clearwater rentals

4.8 Average rating
Clearwater stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Clearwater's top spots, include Clearwater Marine Aquarium, Pier 60, and Clearwater Jolley Trolley
Top-rated Accommodation with a Kayak in Clearwater
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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

Hidden Oasis W Screened Heated Salt Pool / Hot Tub
Enjoy best of Florida in this Updated and Newly Furnished 4 bed, 3 bath with PRIVATE SCREENED HEATED SALT WATER POOL and HOT TUB + FLORIDA ROOM+ GAME ROOM located short 3 miles to the beach. This home is in the quiet neighborhood, close to shopping, restaurants, grocery shops and beach. House accommodates up to 10 guests and has 1 KING BED and 3 QUEEN BEDS and 1 Bunk Bed for sleeping arrangements Both Living room and Florida room have Large Sectional Sofas Grill is available in the backyard

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.

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks
Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

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.

Steps from the Sand - Clean, Stylish 2-BR Condo
AQUA BEACH CONDO - Only 90 steps from the beach, this beautifully updated and perfectly located beach condo offers you the very best of Indian Rocks Beach, a charming and intimate beach town located between Clearwater and St. Pete Beach. Two bedrooms with en-suite bathrooms and large walk-in closets, as well as the lofty living area and modern open kitchen will make you feel like at home. This condo is better equipped than your average vacation rental. Continue to read for more...

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

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.

Waterfront Coastal Condo 2 Blocks to Beach
🌊 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! 🌅🏝️🚤

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront
☀ Bay View Duplex ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music

Your private Waterfront Pool home!
Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422
Popular amenities for Clearwater kayak rentals
Holiday House Rentals with a Kayak

Peaceful Pet friendly 2 BR cottage with hot tub.

Heated saltwater pool|Spacious 4BR/3BA|

Lux Mid-Century Downtown Courtyard+Parking

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Canal-front Sanctuary | Manatees, Pool, Hot Tub

Harbor Villa | Waterfront Pool & Spa | Firepit

Tranquil Bay: Waterfront Home w/ Heated Pool
Cottages with a kayak

Pink Gulfside Cottage, Steps to Beach, Pets OK

Steps2Beach-Walk everywhere-Bikes & gear Included

Little piece of Heaven 2

Little Manatee River Cottage

Escondido Boutique Bungalow in Crystal Beach

Elegant Crystal Beach cottage within sea glimpse

Seaside Cottage- Gulf Waterfront with heated pool

Happy Camper Cottage | Cozy Oasis with Hot Tub
Other holiday rentals with a kayak

Cottage in Paradise.

Oceanfront · Steps to Sand · Free Kayaks

Waterfront Home Golf Cart Walk to Beach

Billy's Beach Bungalow

Gulf-to-Bay Island Apt · Steps to Beach #1

Waterfront Paradise-Steps from the Beach

Waterfront 3/3 Home 3 Blocks to the Beach!

2BR/2BA WFRT Condo with Dock near beach #3
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $269 NZD | $283 NZD | $347 NZD | $250 NZD | $250 NZD | $261 NZD | $275 NZD | $212 NZD | $204 NZD | $209 NZD | $250 NZD | $244 NZD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
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- Rentals with a kayak Pinellas County
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
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- Amalie Arena
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