
Family-friendly vacation 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.

Coastal Escape: heated saltwater pool & beaches
â Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 â Heated saltwater pool â Screened-in lanai â BBQ grill â Large backyard w/ playground â Outdoor dining area â 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds â Renovated kitchen and bathrooms â Open living space - great for family gatherings, movie nights â Children toys and games

Home away from home
Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42â tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65â smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Peteâs, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Guest House in prime location!
This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Soothing Breeze
This is a private studio suit located at Carrollwood community. Easy access to Supermarket, Veterans Express Way. There is a fridge, microwave, coffee maker. TV with Roku , Netflix and spectrum channels with wireless internet.There is a queen size bed, individual futon, full bathroom, small dinning room. Nearby Places: TPA Airport 12 miles, 15 â Raymond James Stadium 11 miles 18â Citrus Park Mall 1.9 miles, 6 â Busch Garden 11 miles, 33 â Adventure Island 11 miles, 28â

Sunset studio.
MY APARTMENT IS LOCATED IN GREAT POSITION OF ACCESS TO DIFFERENT PLACES OF THE TAMPA BAY. 1-TAMPA INTERNATIONAL AIRPORT --- 6.8 MILES --10 MIN. 2 -TAMPA BAY PORT ---- 12 MILES .-- 25 MIN 3 -DOWNTOWN TAMPA --- 11 MILES --- 19 MIN 4- YBOR CITY ----13 MILES----21 MIN 5 - RAYMOND JAMES STADIUM.---- 6.5 MILES -14 MIN 6-WHISKEY JOE'S BEACH .....6.2 MILES---10 MIN 7- CLEARWATER BEACH ---22 MILES--35MIN 8- BUSH GARDEN, ADVENTURE ISLAND --12 MILES---25 MIN

Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Welcome to your cozy studio!
This charming furnished studio apartment is the perfect blend of comfort and convenience, offering everything you need for a delightful living experience: *Fully Furnished *Comfortable Sleeping Area *Equipped Kitchenette *On-Site Laundry Room *Private Parking Space *Private Patio Prime Location: Conveniently located close to shops, restaurants, parks and just 10 minutes away from the breathtaking Clearwater Beach

Private apartment perfectly located in Citrus park
A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

Apart Citrus 15 min from Airport/20 min BushGarden
The apartment is located in the community of Carrollwood Meadows, the neighborhood is quiet and peaceful. 5 minutes from Citrus Park Mall, Chiliâs Grill and Bar, Olive Garden, and other restaurants 15 minutes from the Airport of Tampa and Raymond James Stadium 20 minutes from Bush Garden Parks and Recreation. 40 minutes from Clearwater Beach 20 minutes from Downtown Tampa

Louisa's Cottage
This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmarâs main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

Private Studio-1 Exquisite space/King Bed/Near TPA
Enjoy your stay in Tampa in this cozy, newly remodeled studio! This studio is located at the center of Town and Country and is a short drive from Tampa International Airport (7 miles, which is 14 minutes away from the studio).
Popular amenities for Oldsmar family-friendly rentals
Family-friendly home rentals with a hot tub

Tropical casita

Cozy AF Tiny-House Oasis

Comfort In Holiday

Peaceful Pet friendly 2 BR cottage with hot tub.

Rooms with a Pool

NEW Heated Salt Pool & Spa on Waterfront Canal

Centrally Located Cozy 1-bed Private Cottage!

Cozy Camper + outdoor shower, fire pit & hottub!
Family- and pet-friendly home rentals

Modern and Comfortable One Bedroom Studio

Bay Lake Cottage

Renovated chic Parisian studio

*Special Pricing* Studio Apt, 3 mi from beach

Modern & Spacious Retreat with Private Pool!

Cuddle Sack near RayStadium, TPA, Busch Gar, beach

Beautiful Private entry & yard, non shared space.

Fountain House On Timberbay Lake
Family-friendly home rentals with a pool

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

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

Studio with Pool

Seminole Heights Riverside Paradise w/Pool

Private pool suite in heart of Tarpon Springs!

Tropical Oasis Retreat w/ Heated Pool

By The Pool, No Stairs, NO hidden fees.

Modern Waterfront Condo - Captivating Sunset Views
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,368 ZAR | R3,893 ZAR | R4,130 ZAR | R3,385 ZAR | R3,301 ZAR | R3,114 ZAR | R3,182 ZAR | R3,301 ZAR | R2,945 ZAR | R3,047 ZAR | R3,301 ZAR | R3,301 ZAR |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about vacation rentals that are family-friendly in Oldsmar

Total vacation rentals
Explore 90 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at R846Â ZAR per night before taxes and fees

Verified guest reviews
Over 2,460 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guestsâaveraging 4.8 out of 5!
Destinations to explore
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- Hotel rooms Oldsmar
- House rentals Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with beach access Oldsmar
- Rentals with a patio Oldsmar
- Rentals with pools Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with a washer and dryer Oldsmar
- Pet-friendly rentals Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a hot tub Oldsmar
- Family-friendly rentals Pinellas County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Anna Maria Island
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Cortez Beach
- Vinoy Park
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Busch Gardens
- Don CeSar Hotel




