Family-friendly holiday rentals in Oldsmar

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

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.

Great value!! We loved the pool area and very quiet neighborhood!

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.

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!

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.

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!!

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.

great location far enough away from the chaos, but close enough to be enjoyable. great place for morning walks too.

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.

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!!

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.

What an excellent little place with so many well thought out details! We enjoyed our stay and nothing was lacking! Will definitely look to stay at your properties in the future!

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!

Everything was great! I loved the decorations! Thank you for having me!

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!

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.

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!

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.

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!

This was a great space, loved the outside space, the hosts were very responsive to any questions we had! We loved our stay here.

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.

Lina's place was wonderfully decorated and we felt very at home. The beach was only 2 blocks away and the host provided umbrellas, chairs, cooler and wagon, making our beach day a breeze. There's also pickleball and park nearby. Overall we enjoyed our stay and hope to be back again.

Mathew's place was exactly what I needed. Calm, quiet and very peaceful. I didn't hear the neighbors the whole time I was there. The beach was literally right out the window. So getting down there was very easy. Having a beach chair, cooler and bag in the condo was very convenient. The condo was very clean and homey. I liked being able to cook for myself and never having to leave the complex. I will definitely stay here again!!