
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.

Coastal Escape: heated saltwater pool & playground
★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ 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, 42” 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 - 65” 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 Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Taste Of Florida-10 mi from Tampa Airport
Welcome to our Taste of Florida! This wonderful, private little Coastal gem (nestled in Beautiful Carrollwood and only 10 miles from the airport) is perfectly located and equipped for vacationers, business travelers and those who just want to get away from the hustle and bustle. Whether you are visiting any of the nearby premier hospitals, theme parks, outlet malls or college campuses, this private in-law suite studio is sure to allow you to relax during your stay in the Tampa Bay 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.

California
Hi there , this beautiful studio apartment is a very romantic and peaceful place to stay., very central in one of the best areas in Tampa , also near Tampa internacional airpor, Publix , Walmart a few minutes away. The apartment has also a Murphy bed and a laundry both locked for a an extra charge (AS REQUEST FOR AN EXTRA CHARGE), So if you want to have a real good time in a comfortable studio apartment this is the place to stay -Second bed- 30 per day - Landry- ——$ 20

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 ‘ Raymond James Stadium 11 miles 18’ Citrus Park Mall 1.9 miles, 6 ‘ Busch Garden 11 miles, 33 ‘ Adventure Island 11 miles, 28’

Corner Bay Apartment
Welcome to our cozy apartment, your perfect getaway. Situated just minutes from Tampa International Airport, and popular attractions like Clearwater and St Pete beaches; the Buccaneers (Raymond James Stadium); the famous Yankees Stadium, Tropicana Field, BushGardens, Zoo Tampa at Lowry Park and the Florida Aquarium. This cozy retreat is ideal for couples or solo travelers looking to explore the Tampa area. Enjoy a morning coffee before venturing out to explore the bay.

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

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, Chili’s 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 Oldsmar’s 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.
Popular amenities for Oldsmar family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy AF Tiny-House Oasis

Tropical casita

La Casita, 1 of 4 rentals on-site. Heated Pool!

Rooms with a Pool

Waterfront condo on top floor @ Boca Ciega Resort

Centrally Located Cozy 1-bed Private Cottage!

HOT TUB & Free Wine !, Ping-Pong, Outdoor Theatre

Tiny Lime House, Cozy Modern Bright Garden Retreat
Family- and pet-friendly home rentals

Luxe Apartment | Water Views | Covered Balcony

Modern and Comfortable One Bedroom Studio

Farm and lake stay at Malfini Cay

Wonderful family friendly home in Dunedin FL

Bay Lake Cottage

Charming Guest House in Tampa

Tropical Oasis Retreat w/ Heated Pool

Modern & Spacious Retreat with Private Pool!
Family-friendly home rentals with a pool

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

Tiki Themed Waterfront Condo on Tampa Bay

The Pearl at Ridgewood Park

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

Private pool suite in heart of Tarpon Springs!

Tropical Getaway, Perfect Home & Great Location

Modern Waterfront Condo - Captivating Sunset Views

Clearwater Gameroom- Pool/Mini golf/Home Theatre
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $345 NZD | $399 NZD | $423 NZD | $347 NZD | $338 NZD | $319 NZD | $326 NZD | $338 NZD | $302 NZD | $312 NZD | $338 NZD | $338 NZD |
| 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 holiday rentals that are family-friendly in Oldsmar

Total holiday rentals
Explore 90 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $87 NZD per night before taxes and fees

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oldsmar rentals

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




