
Family-friendly vacation 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

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!
Beautiful townhouse and accommodations were excellent! Very clean, close to the beach and surrounding stores and restaurants. Loved that we were able to use their wagon and beach chairs as well as the bikes to get around. Would definitely stay here again!

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.

Bay Shores Yacht & Tennis Club Indian Shores FL
Great location! Easy walk to the beach. Property has desired amenities. Inside had everything we needed.
Family- and pet-friendly home rentals

Beach 5-Min (Near Tampa & Clearwater)
This is our second year renting this house. Loved the brand new kitchen! The addition of the dishwasher was greatly appreciated. Nice private back yard with new gas grill and lounge chairs.

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.

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!!

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!!

Tiny House Downtown St.Pete: Surprisingly Spacious
Great stay at Alex's place. It was exactly as described. Walkable, safe area. I initially was concerned about the street parking, but Alex explained it completely and it was never a problem. I would definitely stay again.

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

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.

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach
We just had the best family beach vacation at Mindy's place! The location cannot be beat. A very short walk to the beach with ice cream on the way. The pool was so nice to use every day as well. We really appreciated the outdoor shower by the pool to rinse off after the beach as well. The beds were soft and cozy and had everything we needed. We have small kids and so we really appreciated the beach wagons, toys, life jackets, and umbrellas and couldnt have done the beach without them since we flew in. The house is so cute and tropical and really felt like we were on vacation! My kids favorite part was the pool! Mindy went above and beyond to make sure we had everything for our stay and we really appreciated it! Cannot recommend this place enough!

Charming Bungalow w/ Heated Pool - 10 min to beach
Our stay was great! We knew what to expect with a handy binder that was inside the home, info was given to get in the home the day before with clear instruction. It’s an older home but very clean and maintained. There are restaurants and grocery stores very close and makes this convenient for needs during your stay as well.

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 vacation rentals that are family-friendly in Oldsmar
Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ294 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
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Ben T Davis Beach