
Family-friendly holiday rentals in Oldsmar
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oldsmar
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub

Harbor Oasis | Hot Tub | Private | Lush Backyard

Hot Tub, Heated Pool, 2 Master Suites, Beach

Tropical casita

Rooms with a Pool

Charming Tampa Retreat: 2BD/2BA Centrally Located

Waterfront condo on top floor @ Boca Ciega Resort

Tropical Paradise

Private Pool, Jacuzzi, Walk to Beach.
Family- and pet-friendly home rentals

Modern and Comfortable One Bedroom Studio

The Coastal Retreat

Wonderful family friendly home in Dunedin FL

Modern & Spacious Retreat with Private Pool!

Private apartment perfectly located in Citrus park

Fountain House On Timberbay Lake

Cozy suite, full amenitie's, pet friendly

Tropical Paradise
Family-friendly home rentals with a pool

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

Heated & Screened in Pool-All Essentials Provided

J&M Homestead

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Tropical Oasis Retreat w/ Heated Pool

POOL VIEW IN A MODERN CONDO - Feel at Home

Coastal Escape: heated saltwater pool & beaches

Modern Waterfront Condo - Captivating Sunset Views
Quick stats about holiday rentals that are family-friendly in Oldsmar
Total rentals
80 properties
Nightly prices starting at
₹7,047 before taxes and fees
Total number of reviews
2.3K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Rentals with a washing machine and dryer Oldsmar
- Rentals with a firepit Oldsmar
- Rentals with a fireplace Oldsmar
- Hotel rentals Oldsmar
- Waterfront rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Fitness-friendly rentals Oldsmar
- House rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with beach access Oldsmar
- Rentals with pools Oldsmar
- Rentals with outdoor seating Oldsmar
- Family-friendly rentals Pinellas County
- Family-friendly rentals Florida
- Family-friendly rentals 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
- River Strand Golf and Country Club
- Honeymoon Island Beach
- Tampa Palms Golf & Country Club
- North Beach At Fort DeSoto Park
- Fred Howard Park
- Lakewood National Golf Club