
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

Sea Breeze

Private pool, Golf Cart, Completely Renovated!

Luxury Waterfront w/ Private Heated Pool

Beautiful Home, near Honeymoon Beach, Garden Games

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Private Coastal Getaway to Connect and Celebrate

Casa St.George, Centrally Located, Pool, Game Room

Minutes from the Beach
Condo rentals with a pool

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

Seasalt Breeze private unit No hidden fees

Tiki Themed Waterfront Condo on Tampa Bay

Modern and Cozy Condo 6 Minutes from the Beach !

Centrally Located/Pickleball/Pool/Washer/Dryer/Fun

POOL VIEW IN A MODERN CONDO - Feel at Home

Tampa Bay Breeze - Gentle Winds, Stunning Views

Modern Waterfront Condo - Captivating Sunset Views
Other holiday rentals with a pool

The Gallery - Modern Home

Safety Harbor Retreat

NEW Cozy Family Retreat, Tampa: Private Pool Oasis

The Hen House Retreat

Coastal Cottage

East Lake Gem On The Green

Luxe Retreat Paradise

Designers Villa @ Saddlebrook
Quick stats about holiday rentals with a pool in Oldsmar
Total rentals
80 properties
Nightly prices starting at
$31 AUD 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
- Seminole Holiday rentals
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- Pet-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with a patio Oldsmar
- Rentals with a fire pit Oldsmar
- House rentals Oldsmar
- Hotel rentals Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with beach access Oldsmar
- Waterfront rentals Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with pools Pinellas County
- Rentals with pools Florida
- 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
- 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
- Fort De Soto Park