
Vacation rentals with a pool in Clearwater
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Clearwater

Total vacation rentals
Explore 2,020 vacation rentals in Clearwater

Nightly prices starting at
Clearwater vacation rentals start at R168 ZAR per night before taxes and fees

Verified guest reviews
Over 72,900 verified reviews to help you choose

Family-friendly vacation rentals
1,090 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 580 rentals that welcome pets

Rentals with dedicated workspaces
1,100 properties have a dedicated workspace

Wi-Fi availability
1,950 of Clearwater vacation 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 Countryside 12
Top-rated rentals with a pool in Clearwater
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Clearwater Gameroom- Pool/Mini golf/Home Theatre
Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

JOJO'S Beachside 1Acre Estate-New Heated Pool
LUXURY CUSTOM HOME WITH NEW HEATED SALTWATER POOL ONLY 1.5 MILES TO BEAUTIFUL WHITE SAND REDINGTON BEACH ON 1 ACRE OF LAND. HOME HAS JUST BEEN TOTALLY RENOVATED WITH TASTEFUL FINISHES. THIS AREA IS VERY QUIET AND UNIQUE FOR PINELLAS COUNTY WITH LARGER LOTS AND HOMES. 2300 SQUARE FEET WITH HIGH VAULTED CEILINGS. LARGE OPEN KITCHEN, T.V.'S IN EVERY RROM. GREAT LOCATION JUST MINUTES FROM: COFFEE SHOPS , GROCERY STORE, SHOPPING, RESTAURANTS, MOVIE THEATERS AND PARKS. LARGE PAVER DECK BY POOL AREA.

Spacious Home+Guest House w/Huge Pool/Big parking
Enjoy this tastefully decorated home with a separate guest house, perfect for families or groups. Over 2500 sq ft with a huge backyard and pool, just minutes from beaches, theme parks, restaurants & shops. ✨ Highlights: Main house (3+2) + guest house (1+1) Huge backyard & private pool Family-friendly, perfect for gatherings Close to beaches, Splash Harbor Water Park, restaurants Large parking for 7+ cars/RV Convenient location Book your stay and enjoy comfort, style, and fun in one place! :))

Beach Front Madeira Beach
PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

Amazing views on beachfront
This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

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

Specious home W/ Heated Pool ! ! ! Great Location.
Cozy, spacious home 🏡 w/ heated swimming 🏊♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Birthday • Events • Pool • Projector • Volleyball • 10 minutes to the beach
Welcome to your own private resort in the heart of Clearwater! Unlike most vacation rentals, we welcome birthdays, family reunions, and special celebrations for groups up to 22 guests. Located just 10 minutes from world-famous Clearwater Beach, this luxurious 5-bedroom lakefront home offers the privacy, space, and resort-style amenities to create unforgettable memories. Tastefully updated and designed for comfort, this is the ultimate celebration destination for your family!

*Shore Thing* Walk to Beach | Intercoastal Views
🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

Family/Group Getaway w/ Pool Near Clearwater Beach
🏖️ Private pool + 4BR | 9 mins to Clearwater Beach Bring the whole group to this spacious 4-bedroom home designed for relaxing and entertaining. Enjoy a private pool, oversized backyard, and plenty of room for families and friends to spread out. ✔ Sleeps large groups comfortably ✔ Private pool + outdoor space ✔ Fully equipped kitchen + fast WiFi Just minutes from Clearwater Beach, dining, and attractions—your ideal home base for a fun, easy Gulf Coast getaway.

Heated Pool & Spa—Pergola Swings—Palms—Sleeps 10
"Pool was clean and the hot tub was amazing." Viewtop lives up to it. This single-story Clearwater pool home has a heated pool and attached spa, with a wood pergola hung with two porch swings. Coffee in the pergola swings at sunrise, dip in the spa, dinner under the candelabra chandelier, then a movie on the 65-inch Roku. King master, two queens, a queen, and two queen sleeper sofas in the second living room. Eleven minutes by car to Clearwater Beach.

Ocean Breeze • Easy - Heated Pool Access
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport
Popular amenities for Clearwater rentals with a pool
House rentals with a pool

The Palm House | Free Heated Pool!

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Paradise palms oasis Clearwater

Dunedin 5 STAR+ Heated Pool+Near Beach

Clearwater Pool Home w/ King Bed, BBQ & Fire Pit!

The Palm Haus • Heated Pool • Near Beach • Games

Piece of paradise in Indian Rocks Beach.

3 BR/2B pool home WiFI and Brand new furnishings
Condo rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Modern and Cozy Condo 6 Minutes from the Beach !

Free Parking Pool & Water Front

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Brand New, Beautiful and Specious Waterfront Condo

Beachfront Condo in Exclusive Resort
Other vacation rentals with a pool

Fantastic Condo at Avalon - Fully Renovated

Beachfront Oasis / Pool, Beach Access & Ocean View

Largo Palms Duplex-2BR/2BA + Heated POOL Unit A

Clearwater Mediterranean Retreat • Pool & Fire Pit

Luxury Clearwater Home • Heated Pool + Near Beach

Clearwater Vacation Rental Condo/Heated Pool

Tranquil Bay: Waterfront Home w/ Heated Pool

Beautiful One Bedroom Avalon At Clearwater
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,194 ZAR | R3,867 ZAR | R4,337 ZAR | R3,581 ZAR | R3,009 ZAR | R3,060 ZAR | R3,177 ZAR | R2,757 ZAR | R2,589 ZAR | R2,572 ZAR | R2,875 ZAR | R2,976 ZAR |
| 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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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
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