
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

Hot Tub, Heated Pool, 2 Master Suites, Beach

Tropical casita

Comfort In Holiday

Rooms with a Pool

Tropical Paradise

Private Pool, Jacuzzi, Walk to Beach.

Centrally Located Cozy 1-bed Private Cottage!

Breathtaking Waterview & Pool View Condo
Family- and pet-friendly home rentals

Modern and Comfortable One Bedroom Studio

Midtown Mod w/King Bed+Fooseball

Taste Of Florida-10 mi from Tampa Airport

Villa cashita, private accommodation,

Wonderful family friendly home in Dunedin FL

Modern & Spacious Retreat with Private Pool!

Private apartment perfectly located in Citrus park

“The Tiny Paradise”
Family-friendly home rentals with a pool

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

Heated Pool, 10 min to Beach, Close to Restaurants

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

Private pool suite in heart of Tarpon Springs!

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
$139 NZD 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
- Miami Holiday rentals
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Destin Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Pet-friendly rentals Oldsmar
- Rentals with pools Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with a fireplace Oldsmar
- House rentals Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with beach access Oldsmar
- Waterfront rentals Oldsmar
- Rentals with outdoor seating Oldsmar
- Hotel rentals Oldsmar
- Rentals with a patio 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
- 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