
Vacation rentals with a pool in Clearwater
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Clearwater
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Clearwater rentals with a pool
House rentals with a pool

Tootsie’s Beachside Retreat

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Your Dream Kitchen at the Beach! Pool & golf cart!

Palm Oasis | Heated Pool | Near Beaches

FL Gem! XL Pool | Pickleball | B-Ball & More!

Iconic PINK Beach Retreat!

Palm Paradise - Family Amenities+Central Location
Condo rentals with a pool

Spotless 2 BR/2 BA Retreat w/ A+ Pool, 3m to Beach

Relax in a Newly Renovated Beach Front Paradise

Beach Haven in South Clearwater Beach

Modern and Cozy Condo 6 Minutes from the Beach !

Resort living in paradise

Beachfront Condo with Centerline Sunsets

Spectacular beach to bay views from this resort.

2025 Renovated Suite On The Beach - Heated Pool
Other vacation rentals with a pool

Brand new! Ground Pool Side Condo Clearwater!

SEPT DEAL 10%OFF | Newly Remodeled | Walk to Beach

Avalon. Clearwater. Cozy condo. Pool view.

Welcome to your vacation home

Pool | Patio | Kitchen | Gym | Self Checkin | WiFi

Sonrisa 1 - | Beachfront Condo in Belleair Beach

Clearwater retreat: Luxury Spa & Comfort Stay

CHARMING CLEAN CLEARWATER! Steps to WALMART!!
Quick stats about vacation rentals with a pool in Clearwater
Total rentals
1.8K properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
64K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
420 properties allow pets
Rentals with dedicated workspaces
960 properties have a dedicated workspace
Destinations to explore
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- Rentals with a hot tub Clearwater
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- Rentals with pools Pinellas County
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- Rentals with pools United States
- Anna Maria Island
- Weeki Wachee Springs
- Dunedin Beach
- John's Pass
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Anna Maria Public Beach
- Amalie Arena
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- Jannus Live
- North Beach
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Fred Howard Park
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