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

Waterfront Townhome w/Game Room & Boat Slip! Walk
PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Neptune's Nest | Amazing Htd Pool | Steps to Beach
An original early 1900 Indian Rocks Beach bungalow, updated with all the comforts of home. Grill on your private patio or relax in the pool area in our tropically landscaped grounds. Cross Gulf Boulevard to 8th Ave beach access to the beautiful turquoise waters and white sandy beaches of the Gulf of Mexico. Enjoy swimming, shelling and fishing as you live the island life. Splash Harbour water park, shops and restaurants are within walking distance. Come for an unforgettable stay! City tax#1479

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

Private Beachfront 2BR BUNGALOW*POOL*PETS ok
DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

Beachfront in exclusive resort
This upper floor, 3-bedroom modern chic condo hotel suite offers sweeping views of the Gulf of Mexico from private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the shrimp trawlers making their way out to sea. Enjoy a cocktail while watching the sunset over the open water of the Gulf of Mexico. This suite can sleep 8, with King or Queen-size beds in each of the three bedrooms, a comfortable full-sized sofa bed in the living room & 3-1/2 bathrooms.

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6
🌴 Your Clearwater Beach Escape Starts Here Wake up to peaceful water views, sip coffee on your private patio, and end your day watching the sunset just minutes away on the beach. This spacious 2BR/2BA condo perfect for families, couples, or small groups looking for a relaxing getaway.Quiet location while still being close to everything Waterfront patio with serene views (yes, dolphins are often spotted 🐬) Walk to Clearwater Beach, restaurants, and shops Pool for relaxing after the beach

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Relax in a Newly Renovated Beach Front Paradise
Immerse yourself in the stunning beauty of the Gulf Coast at this hidden gem, perfectly nestled in the charming Indian Shores. This property exudes a coastal ambiance, providing a tranquil sanctuary to bask in the sugar-white sands and sparkling turquoise waters. Beach chairs & towels are thoughtfully provided. All you need to bring is a swimsuit & toothbrush. Exciting updates include new furniture & bedding added in '25 as well as a beautifully renovated walk-in shower in '24.

3 Bedroom Waterfront Paradise Sleeps 8
Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach on the intercostal! The 3 floors of custom interior decoration and high end furnishings await you. Located on Clearwater Bay with an easy stroll (5-10 min) to Clearwater Beach, Beach Walk, Pier 60, restaurants, and shopping. You are centrally located to everything in Clearwater with luxury accommodations ! !! You have a 2 car garage, community pool, hot tub, grill steps from your back door.

*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.

Newly Reno Luxury Condo 30 Steps to Paradise
Welcome to our serene top-floor beach condo. This is a two-bedroom, two-bathroom condo in the heart of Clearwater Beach. This ocean-side condo is steps from the country's #1-rated beach and less than a five-minute walk from top restaurants and shopping. Clearwater Beach is renowned for its award-winning beaches, incredible restaurants, and lively nightlife. We have made every effort to make this condo a home away from home! We hope you enjoy our piece of paradise.

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.
Popular amenities for Clearwater Beach rentals with a pool
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Paradise palms oasis Clearwater

Casa Flamingo - Private - Outdoor Bar+TV - Games

Private pool, Golf Cart, Completely Renovated!

Stunning views! Spot dolphins from the pool!

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Clearwater Gem! XL-Pool | Courts & More!

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach
Condo rentals with a pool

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

COASTAL CHIC! Luxury Apartment with Oceanviews

Rincón Divino MB 2 Balconies, Ocean & Marina Views

Beach Across the St | No Stairs |Parking in Front!

Beautiful condo on the beach with heated pool!

Beachfront Condo with Centerline Sunsets

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Sandy Feet Retreat
Other vacation rentals with a pool

Beachfront Oasis / Pool, Beach Access & Ocean View

2/2 located at JW Marriott on Clearwater Beach 710

Private Oasis ~ Pool & Hot Tub ~ 5 Min to Beach

Waterfront Oasis 3BR/4 beds~few min walk to beach.

Four Bedroom Presidential, Clearwater A820

Waterfront with Dock, Heated Pool, Kayaks, Games

Luxury Ocean Front Duplex

Beachfront Getaway with Resort-Style Pool
When is the best time to visit Clearwater Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $279 CAD | $361 CAD | $427 CAD | $339 CAD | $272 CAD | $286 CAD | $290 CAD | $243 CAD | $231 CAD | $228 CAD | $251 CAD | $272 CAD |
| 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 |
Quick stats about vacation rentals with a pool in Clearwater Beach

Total vacation rentals
Explore 1,100 vacation rentals in Clearwater Beach

Nightly prices starting at
Clearwater Beach vacation rentals start at $69 CAD per night before taxes and fees

Verified guest reviews
Over 42,630 verified reviews to help you choose

Family-friendly vacation rentals
550 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 260 rentals that welcome pets

Rentals with dedicated workspaces
590 properties have a dedicated workspace

Wifi availability
1,080 of Clearwater Beach vacation rentals include wifi access

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

4.8 Average rating
Clearwater Beach stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with a firepit Clearwater Beach
- Rentals with a washer and dryer Clearwater Beach
- Rentals with outdoor seating Clearwater Beach
- Beach condo rentals Clearwater Beach
- Aparthotel rentals Clearwater Beach
- Rentals with a kayak Clearwater Beach
- Rentals with lake access Clearwater Beach
- Rentals with a fireplace Clearwater Beach
- Rentals with a sauna Clearwater Beach
- Hotel rooms Clearwater Beach
- Rentals with a patio Clearwater Beach
- Waterfront rentals Clearwater Beach
- Rentals with beach access Clearwater Beach
- Luxury rentals Clearwater Beach
- Apartment rentals Clearwater Beach
- Townhouse rentals Clearwater Beach
- Beachfront rentals Clearwater Beach
- Condo rentals Clearwater Beach
- Rentals with a hot tub Clearwater Beach
- Rentals with breakfast Clearwater Beach
- Cottage rentals Clearwater Beach
- Rentals with an accessible height bed Clearwater Beach
- Pet-friendly rentals Clearwater Beach
- House rentals Clearwater Beach
- Beach house rentals Clearwater Beach
- Boutique hotels Clearwater Beach
- Family-friendly rentals Clearwater Beach
- Rentals with an accessible height toilet Clearwater Beach
- Fitness-friendly rentals Clearwater Beach
- Villa rentals Clearwater Beach
- Bungalow rentals Clearwater Beach
- Rentals with an EV charger Clearwater Beach
- Rentals with pools Clearwater
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Weeki Wachee Springs
- Coquina Beach
- Lido Key Beach
- Amalie Arena
- Vinoy Park
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- Hard Rock Casino
- St Pete Beach
- Anna Maria Public Beach
- Jannus Live
- River Strand Golf and Country Club
- ZooTampa at Lowry Park
- Tropicana Field
- University of South Florida
- Busch Gardens





