
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.

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.

Davenport Dream Suite
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. Small computer table. 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’

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.

Y&O Castle
Tu hogar lejos de casa 🏡 Disfruta de un espacio acogedor, moderno y perfectamente ubicado para tus vacaciones en Tampa. A solo minutos de restaurantes (McDonald’s, Olivos, Michael’s Kitchen y Church’s Chicken) supermercados, bancos y todo lo que necesitas. A 15 minutos del Aeropuerto Internacional de Tampa, 20 minutos de Busch Gardens y a 35 minutos de las playas más hermosas como Clearwater y Honeymoon Island. Ideal para relajarte, explorar y sentirte como en casa. 🌴☀️

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

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

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.

Cozy 1 bedroom apartment 10 min from TPA
Enjoy easy access to everything from this perfectly located home base. We are just 10 mins away from the airport. Our home is located in a quite neighborhood where you can relax and rest. This place was recently renovated so you will be enjoying modern luxury.

Cozy Red Door Studio
Keep it simple at this peaceful and centrally located place. Very cozy and private with a carport parking spot. Close to beaches, shopping, Tampa International Airport, Busch Gardens and more!
Popular amenities for Oldsmar family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy AF Tiny-House Oasis

Tropical casita

Tiki Hut Cottage

Coastal Bliss with hot tub - 4 miles to beaches

Lovely 2-bedroom private Apt. with hot tub.

Rooms with a Pool

Centrally Located Cozy 1-bed Private Cottage!

HOT TUB & Free Wine !, Ping-Pong, Outdoor Theatre
Family- and pet-friendly home rentals

Modern and Comfortable One Bedroom Studio

Studio with Pool

Villa cashita, private accommodation,

Luxury Modern Tiny Home

Modern & Spacious Retreat with Private Pool!

Private apartment perfectly located in Citrus park

Private Guest House

Tropical Paradise
Family-friendly home rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

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

Seminole Heights Riverside Paradise w/Pool

Private pool suite in heart of Tarpon Springs!

Tropical Oasis Retreat w/ Heated Pool

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Modern Paradise home near Clearwater Dunedin Beach
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $258 SGD | $299 SGD | $317 SGD | $260 SGD | $253 SGD | $239 SGD | $244 SGD | $253 SGD | $226 SGD | $234 SGD | $253 SGD | $253 SGD |
| 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 $65 SGD per night before taxes and fees

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

Pet-friendly holiday rentals
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

Wifi availability
90 of Oldsmar holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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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- 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
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- North Beach
- River Strand Golf and Country Club
- Adventure Island
- Tampa Palms Golf & Country Club
- Splash Harbour Water Park
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Busch Gardens
- Don CeSar Hotel




