
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 & 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

"Chic/cozy Petite Studio •"Spa-Inspired Shower. 1”
Welcome to your serene hideaway in Citrus Park, where modern comfort meets thoughtful design. Just 11 minutes from Tampa International Airport, and free parking on premises this stylish and private studio is the perfect spot for couples, solo travelers, or business guests seeking a peaceful and rejuvenating stay. Located in a quiet, safe, and central neighborhood, you’ll enjoy a private entrance, free on-site parking, and easy access to restaurants, grocery stores, and major Tampa attractions.

Monterey Suite at Citrus Park
You will enjoy a sparkly clean Studio Suite with a private patio area and a peaceful lake view, comfortable adjustable queen bed, full bathroom, cute kitchen and computer station with high speed internet. Conveniently located ,14 minutes to airport/toll , walking distance to Super Walmart. Minutes to Citrus Park Mall , AMC Theaters , Publix, Costco, Sprouts, Airport, Busch Gardens, Raymond James Stadium, NY Yankees Training Camp, Upper Tampa Bay Trail were you can rent bikes and many more.

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

cozy small apartment in the middle of tampa
Centrally located in the heart of Tampa Fl. This apartment has been recently renovated with WIFI, TV and Netflix included in the Bedroom. The apartment is just 10 minutes from Tampa International Airport, 10 minutes from the Tampa bucs Stadium, 12 minutes from Downtown Tampa, 10 minutes from Busch Gardens Tampa Bay, 10 minutes from the Zoo and just 35 minutes from Clearwater Beach and so much more ! You will love staying minutes from finest restaurants Tampa Bay has to offer.

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’

Entire Guest House near Tampa airport
Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

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

Tiny House Oasis | Best Location | Outdoor Shower
Despite its size, this tiny home has all you need! This ideal and quiet space is located in downtown Safety Harbor literally around the corner from Main Street. This light, private and airy gem comes completely equipped to hang out for a while. See what all the tiny home excitement is about! Now with new AC mini split for quieter and more comfortable air.

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.

BeachBunkies Cottage 1. Four miles to the beach!
Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities.
Popular amenities for Oldsmar family-friendly rentals
Family-friendly home rentals with a hot tub

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

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

Peaceful Pet friendly 2 BR cottage with hot tub.

The perfect lake house getaway near the airport.

Rooms with a Pool

FREE Heated Pool & Spa l Book your Winter Vacation

Centrally Located Cozy 1-bed Private Cottage!

Grove Keepers Cottage
Family- and pet-friendly home rentals

Modern and Comfortable One Bedroom Studio

The Coastal Retreat

Taste Of Florida-10 mi from Tampa Airport

Bay Lake Cottage

Cottage on Pinellas Bike Trail

Charming Guest House in Tampa

Modern & Spacious Retreat with Private Pool!

Private apartment perfectly located in Citrus park
Family-friendly home rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool

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

Seasalt Breeze - Easy pool access, Free parking.

Dunedin 5 STAR+ Heated Pool+Near Beach

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

Tropical Oasis Retreat w/ Heated Pool

Heated SW Pool - Near Beaches, Golf, Trail & Food

Literally: 15 steps to the Pool, GroundFloor Condo
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,611 GYD | G$48,093 GYD | G$51,020 GYD | G$41,820 GYD | G$40,775 GYD | G$38,474 GYD | G$39,311 GYD | G$40,775 GYD | G$36,383 GYD | G$37,638 GYD | G$40,775 GYD | G$40,775 GYD |
| 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 G$10,455 GYD per night before taxes and fees

Verified guest reviews
Over 2,520 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
60 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 guests—averaging 4.8 out of 5!
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- Family-friendly rentals Pinellas County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Splash Harbour Water Park
- Busch Gardens
- North Beach At Fort DeSoto Park
- The Don CeSar
- Lakewood National Golf Club
- Fred Howard Park




