
Family-friendly holiday rentals in Oldsmar
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Top-rated family-friendly rentals in Oldsmar
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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.
This was our 2nd stay and it was just as pleasant as the first time! The extremely short walk right across the street to the beach, quiet neighborhood, less crowded section of the beach, along with the close proximity to restaurants makes it the perfect little getaway! It's probably the most well stocked home with everything you can think of needing (including both a hot pot and tea pot for your tea, beach towels, beach chairs, wagons, boogie boards ECT) It's a clean, comfortable place that makes us feel right at home. We also love the option of the hot tub to relax in for the evening. The hosts are very kind/helpful. It's the perfect little beach getaway. Thank you again! This place has a special place in our hearts. Happy memories made!

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

Historic Bungalow with Private Pool in Ybor City
Great location, great character, great value. Pool was an excellent space to hang out at during the day and nice central location for everything else. Would stay again.

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!

Pool + Park + Private = Perfect Place
This is the second time we've been able to book this home and if it's available I will book it again when we return. There is a park and walking trails across the street. The trails go along the Hillsborough River where you can see all the fun Florida birds. The accommodations are fantastic. It is clear the hosts care about details, including fluffy towels and sample shampoos and conditioners in the bathroom. I also appreciate the water pressure and quickness of the hot water tank to heat the water in the shower. This kitchen has everything you need if you want to cook. There are beach towels to use for the pool, as well comfortable deck chairs and floats. The hosts were very responsive, and asked if they could come over to clean the pool after an unusually heavy rain. Our family would love to stay there again when we visit Tampa.

Waterfront Beach House Steps Away from #1 Beach!
We absolutely loved this space! We do an annual girls trip to Florida and we were so incredibly happy with the house, layout, amenities, cleanliness and location. Instructions were clear and posting is exactly as described. Can walk to everything in Clearwater from here. We cannot wait to go back!!

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

Tiny rental +patio+BBQ+2bikes+Parking- great area!
It was exactly what I needed while checking out the area

Beach 5-Min (Near Tampa & Clearwater)
great location far enough away from the chaos, but close enough to be enjoyable. great place for morning walks too.

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!!

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!

Studio Zen
I thought the place was perfect for me and my family and would stay there again in a heartbeat

Serene French Country Cottage near everything
We were in Dunedin for a family party, the place had plenty of spots for the seven of us to have a little alone time when needed. We all enjoyed the eclectic decor too!

Private & Cozy Tiny Home/Cottage
Everything was great! I loved the decorations! Thank you for having me!

Waterfront Coastal Condo 2 Blocks to Beach
We had a great time staying here. I caught myself saying that every time I’m in town, I’d try to stay here. Waking up and sitting by the dock with some coffee was pretty great. The guys working the office and the water sports were very nice also. Definitely recommend staying here for small groups!
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.

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.

Renovated Condo! Across the Street From The Beach
being 7 months pregnant this place was perfect for a quick baby moon! the beach is just a walk across the street, plenty of restaurants less than a 5 minute drive and had everything we needed for the beach as well.

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.

☼ BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES
We enjoyed our stay here ! There was a lot of room for the 5 of us. Everything you will need is in the home. The gated community felt safe. The area is perfect only a 7 minute drive to beach ! The pool was beautiful and nice. Do note this condo is on the 3rd floor and has stairs only. It was not a issue for us ! Parking was not a issue , plenty of spaces. Check in and out was easy no issues. We would definitely book with Agnes and Paul again in the future :)

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
₹6,923 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
- Cortez Beach
- 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
- North Beach At Fort DeSoto Park
- Ben T Davis Beach