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Family-friendly holiday rentals in Oldsmar

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oldsmar family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Home in Tampa
5 out of 5 average rating, 188 reviews

Multi-Award Winning & Top 5% Rated on Airbnb 2025

TheresaRating, 5 stars1 week ago
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
Top guest favourite
Home in Clearwater Beach
4.97 out of 5 average rating, 119 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.

CynthiaRating, 5 stars1 month ago
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!
Superhost
Home in Largo
4.79 out of 5 average rating, 425 reviews

Spacious Home Solar-Heated Pool and Spa

ValerieRating, 5 stars2 months ago
Great value!! We loved the pool area and very quiet neighborhood!
Guest favourite
Bungalow in Ybor City Historic District
4.77 out of 5 average rating, 321 reviews

Historic Bungalow with Private Pool in Ybor City

StephenRating, 5 stars2 weeks ago
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.
Top guest favourite
Apartment in St. Petersburg
4.98 out of 5 average rating, 268 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

SarahRating, 5 stars1 week ago
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!
Top guest favourite
Home in Tampa
4.99 out of 5 average rating, 281 reviews

Pool + Park + Private = Perfect Place

SharonRating, 5 stars2 weeks ago
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.
Top guest favourite
Townhouse in Clearwater Beach
5 out of 5 average rating, 122 reviews

Waterfront Beach House Steps Away from #1 Beach!

MariannaRating, 5 stars2 weeks ago
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!!
Guest favourite
Flat in St. Petersburg
4.9 out of 5 average rating, 171 reviews

The Oasis

CherieRating, 5 stars1 week ago
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

Guest favourite
Tiny home in St. Petersburg
4.79 out of 5 average rating, 248 reviews

Tiny rental +patio+BBQ+2bikes+Parking- great area!

AmandaRating, 5 stars3 weeks ago
It was exactly what I needed while checking out the area
Guest favourite
Home in Seminole
4.96 out of 5 average rating, 123 reviews

Beach 5-Min (Near Tampa & Clearwater)

BrittneyRating, 5 stars6 days ago
great location far enough away from the chaos, but close enough to be enjoyable. great place for morning walks too.
Superhost
Flat in Dunedin
4.91 out of 5 average rating, 213 reviews

Downtown Dunedin B&B - Rustic Cabin with Pool

HadenRating, 5 stars1 week ago
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!!
Top guest favourite
Home in St. Petersburg
4.9 out of 5 average rating, 376 reviews

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

EdgarRating, 5 stars3 weeks ago
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!
Guest favourite
Guest house in Dade City
4.83 out of 5 average rating, 248 reviews

Studio Zen

DanielRating, 5 stars1 week ago
I thought the place was perfect for me and my family and would stay there again in a heartbeat
Guest favourite
Cottage in Dunedin
4.8 out of 5 average rating, 125 reviews

Serene French Country Cottage near everything

CheriRating, 5 stars1 month ago
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!
Guest favourite
Guest house in St. Petersburg
4.85 out of 5 average rating, 845 reviews

Private & Cozy Tiny Home/Cottage

HadleyRating, 5 stars2 weeks ago
Everything was great! I loved the decorations! Thank you for having me!
Guest favourite
Flat in Clearwater Beach
4.87 out of 5 average rating, 126 reviews

Waterfront Coastal Condo 2 Blocks to Beach

LeahRating, 5 stars3 weeks ago
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

Guest favourite
Apartment in Redington Beach
4.9 out of 5 average rating, 163 reviews

SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA

TatyanaRating, 5 stars3 weeks ago
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.
Top guest favourite
Guest house in St. Petersburg
4.9 out of 5 average rating, 326 reviews

Carriage House in North St. Pete

GraceRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Tampa
4.93 out of 5 average rating, 400 reviews

Tampa Events & Suite w/WtrFrt Bay & Sunset Views

SheilaRating, 5 stars1 month ago
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.
Guest favourite
Bungalow in Tampa
4.75 out of 5 average rating, 106 reviews

1920s Bungalow Cottage with Saltwater Pool!

HopeRating, 5 stars2 weeks ago
This was a great space, loved the outside space, the hosts were very responsive to any questions we had! We loved our stay here.
Guest favourite
Apartment in Indian Rocks Beach
4.96 out of 5 average rating, 116 reviews

Renovated Condo! Across the Street From The Beach

RachaelRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Clearwater
4.94 out of 5 average rating, 141 reviews

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

AlecRating, 5 stars2 weeks ago
Great location, and host provided everything we could need whether it’s at the apartment or at the beach.
Superhost
Flat in Clearwater
4.89 out of 5 average rating, 120 reviews

☼ BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES

TrishRating, 5 stars2 weeks ago
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 :)
Guest favourite
Flat in Clearwater Beach
4.89 out of 5 average rating, 217 reviews

Waterfront Modern Chic #1 Clearwater Beach

MichaelRating, 5 stars1 week ago
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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