
Holiday 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.
Holiday 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

*1Der Stays* #1 Cozy 3 bedrooms home with pool.

Entire house in Tampa w/ Heated POOL!

Private pool, Golf Cart, Completely Renovated!

Lizard Lodge - Remodeled with Pool & Florida Room

Tropical Getaway w/Heated Pool & King Beds

Luxurious House with private Pool.

Lavish Heated Saltwater Pool Home Mins. to Beach

Heated Pool | 2BD 2BA | Home near Beaches
Apartment rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

Seaside Paradise at Clearwater - Resort Style

Royal Orleans and Redington Beach ( Studio )

Modern and Cozy Condo 6 Minutes from the Beach !

Boho Beach Condo

Tropical Serenity-Water View, Heated Pool Tiki Bar

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

Easy Pool access, No stairs. King Bed
Other holiday rentals with a pool

Paradise by the Park

The Coastal Calm - Entire Unit

Pool~Waterfront~Central~Tiki Bar~Tampa, FL

Sunny's Retreat

Zen Boho 3BR/2BA Pool, Ping Pong, BBQ,Near Airport

Coastal Cottage

East Lake Gem On The Green

Tampa Tropical-Saltwater Pool-10 Min to TPA
Quick stats about holiday rentals with a pool in Oldsmar
Total rentals
80 properties
Nightly prices starting at
£15 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
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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- Rentals with outdoor seating Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with a firepit Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with beach access Oldsmar
- House rentals Oldsmar
- Waterfront rentals Oldsmar
- Hotel rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Weeki Wachee Springs
- John's Pass
- Dunedin Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Coquina Beach
- Anna Maria Public Beach
- Cortez Beach
- Amalie Arena
- Vinoy Park
- Gulfport Beach Recreation Area
- Jannus Live
- North Beach
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- Honeymoon Island Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- North Beach At Fort DeSoto Park
- Fred Howard Park
- Busch Gardens