
Vacation rentals with a pool in Oldsmar
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oldsmar
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 Oldsmar rentals with a pool
House rentals with a pool

Heated & Screened in Pool-All Essentials Provided

Near Beach, Heated Pool, Backyard Games, Fire Pit

Clearwater retreat: Luxury Spa & Comfort Stay

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

your home close to everything

Luxurious House with private Pool.

Rooms with a Pool

Angelita's Lake Home 3br3ba w/heated pool
Condo rentals with a pool

Tampa Events & Suite w/WtrFrt Bay & Sunset Views

Seasalt Breeze private cozy unit

Very cozy quality condo close to Clearwater Beach

Lakeside 2- Bed Apartment Near Clearwater Beaches

Bright and Spacious 1Bed/1Bath condo.

Rocky Point paradise

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Quick stats about vacation rentals with a pool in Oldsmar
Total rentals
70 properties
Nightly prices starting at
$27 CAD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Anna Maria Island
- Weeki Wachee Springs
- Dunedin Beach
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- John's Pass
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- Busch Gardens Tampa Bay
- Raymond James Stadium
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- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Ben T Davis Beach