
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

Multi-Award Winning & Top 5% Rated on Airbnb 2025
Great location, Jason’s eye to detail was perfect. He was responsive to every call. The house was absolutely beautiful. It was a peaceful time and minutes from the stadium and Ybor

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.
We had a great time staying here in Clearwater. SO close to the beach. Their place was clean and was ready for a family to stay. We look forward to coming back.

Spacious Home Solar-Heated Pool and Spa
Great value!! We loved the pool area and very quiet neighborhood!

Crescent Beach House Pet friendly
This was the perfect location for our family. We loved the proximity to the beach and restaurants. The place was clean and well stocked. Would love to come back.

Ultra Modern Pool Home w/ rooftop private HOT TUB
Great place to stay if you are heading to a BAESBALL game or an EVENT at RAYMOND JAMES STADIUM ! This is the PERFECT spot ! An easy walk

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209
Just like the photos! Beautiful and comfortable for our stay… Love the location, close to everywhere we wanted to go! Comfortable bed, the couch could use some updating. The pool is very warm, but a nice spot to hang out. Didn’t get to see any dolphins 😞 Overall, enjoyed our stay, will definitely be back!

Beach Front Condo 3 bathrooms 3 bedrooms/5 beds
I loved the apartment very well equipped for everything you need to cook. The apartment has an amazing view, location is great, close to everything from restaurants, grocery stores, pharmacies, etc. I loved it!

The Oasis
Russell’s place was just as described. The bay of the bay was beautiful! This condo was within short driving distances of many great local beaches and restaurants. It had all the amenities, linens, and other items needed to make our stay perfect. Russell checked in with us prior to our stay, during and after.
Family- and pet-friendly home rentals

Adorable Dog-Friendly Cottage in Quaint Dunedin
We absolutely love staying at this property! It is our third time booking. The cottage is always impeccably clean and in a very safe area. It is stocked with everything you need. We love Coral Cottage! And Barbara is very friendly and so responsive. Dunedin is an amazing, quaint little town with so many wonderful food choices. Cafe' Alfresco is our personal favorite. Barbara's cottage is just a couple blocks from downtown Dunedin and only a 15 minute drive to Honeymoon Island State Park or Clearwater beach. I always pick up a piece of jewelry as a memento when we go on a trip. Just kitty-corner from the Airbnb is a charming jewelry store filled with beautiful, unique pieces that are reasonably priced. Romantique Jewelers. Just ask for Kimber, she's a doll! Don't hesitate to book this property for your next trip!!!

Downtown Dunedin B&B - Rustic Cabin with Pool
Great place with a huge pool and the walk to downtown and surrounding shops was a stones throw away. The host answered with any questions we had promptly and provided my girlfriend and I was an outstanding stay! I would love to stay with you guys again as soon as I can! Thanks for a great weekend in Dunedin! What an awesome little town!!

Waterfront, Sunsets & Heated Pool & Pet Stay Free!
My fiancé and I along with our dogs had a great time staying at Elaine’s place! The house & views were beautiful. We will definitely be back.

Seminole Heights Riverside Paradise w/Pool
We felt at home-didn’t need anything extra-that had taken care of the details including every kitchen utensil/ item you would need. Ryan was great with communication and asked in advance if we had any needs. Such a peaceful property right on the river. We enjoyed the pool most afternoons-refreshing! Central location too! We will be visiting again for sure!

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!
My stay at Stephanie's property was very pleasant. I never had to call her. Everything at her property is excellent. The house is spectacular, the pool was GREAT!!!, and the fire pit was the best. I have no hesitation in recommending her property. Thank you, Stephanie!

Private Beach Bungalow 1BR *Heated POOL**PETS ok
We recently wrapped up an AMAZING stay at The Lobster Beach Bungalow. Everything was as described- charming ‘old Florida’ feel and close proximity to the beach (50 steps). It felt like a miniature resort. We got to meet other vacationers staying at the other bungalows, which was pretty cool. We were even able to enjoy the pool on a day where the gulf waters were a little rougher. There are a lot of eateries within walking distance. We tried a different coffee shop every morning- yum! The bungalow itself was comfortable and had everything we needed for a great stay. The kitchen had we could have desired should we have decided to eat in. Too many yummy local eateries for that for us though! We also loved being able to have our fur babies with us, as no vacation is complete without our whole family. We look forward to returning next year with some extended family to experience this peaceful paradise. Thank you, Liz, for creating a place that feels like home away from home!

Baby Bungalow close to Downtown!
This adorable bungalow was perfect for a long weekend getaway! They have all of the amenities, it is centrally located, it's clean, and they communicated very well. I will definitely come again and recommend your place!!

First-Rate Location! Just Steps to Exquisite Beach
Short walk to the beach, food and coffee.
Family-friendly home rentals with a pool

SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA
Perfect location, 4 minutes walk to beach. Nice, clean and worn swimming pool. Quiet area. Room was clean and comfortable. All needed for beach life. Fully equipped convenient kitchen.

Carriage House in North St. Pete
We had a wonderful stay here! It was very close to everything we wanted to do and their hospitality was phenomenal. We hope to come back and stay again sometime!

Tampa Events & Suite w/WtrFrt Bay & Sunset Views
Such an awesome place to stay with amazing views. Clean and had extra essentials which makes it nice. Loved the fan and TV above the bed and the large shower. I traveled alone and felt completely safe. I would definitely stay again.

Gulf view Condo with pool in Clearwater/St. Pete
I stayed for 5 nights at this Airbnb, it was easy to find and get into with the pictures and thorough instructions! When I walked in everything was just like the pictures and it was very clean and comfortable. It is small like she says but it worked perfectly for my friend and I. The walk to the beach is super close and the trolley system is really helpful if you can’t or don’t want to drive to nearby places. The host was very friendly and responsive, I would definitely recommend staying here and would go back!

1920s Bungalow Cottage with Saltwater Pool!
This was a great space, loved the outside space, the hosts were very responsive to any questions we had! We loved our stay here.

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach
We were looking for a quick family vacation at the Gulf of America and we found this little gem at Indian Rocks Beach. The location was perfect and only 30 min from the airport. With all equipment provided to be at the beach and only a short walk across the street, it was just what we needed. There's a cool little ice cream and sandwich shop right across the street Kooky Coconuts offering the best Cuban sandwich in Florida and great ice-cream. Sleeps 4 comfortably and has a great tiki bar in the back. If your looking for relaxation, great restaurants and beach, this is the place. Owners are awesome and where always available if we needed anything. Definitely will be back!

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/
Great location, and host provided everything we could need whether it’s at the apartment or at the beach.

Waterfront Modern Chic #1 Clearwater Beach
My family and I had such an amazing time staying at Lina's place! The apartment is even more beautiful than the picture suggest. It was absolutely spotless and we had such a nice time hanging in the pool as well as sitting out back and watching the boats go by. The beach is a quick 5 minute walk away as well as several other dining spots. Would love to come back again soon!
Quick stats about holiday rentals that are family-friendly in Oldsmar
Total rentals
80 properties
Nightly prices starting at
$134 NZD before taxes and fees
Total number of reviews
2.2K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Public Beach
- Dunedin Beach
- John's Pass
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
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- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
- Adventure Island
- Splash Harbour Water Park
- Tampa Palms Golf & Country Club
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- Ben T Davis Beach