
House holiday rentals in Oldsmar
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Top-rated house rentals in Oldsmar
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Holiday rentals for every style
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Popular amenities for house rentals in Oldsmar
House rentals with a pool

Heated & Screened in Pool-All Essentials Provided
Very clean and very well equipped. House was very responsive and even checked in on us mid stay to see if we needed anything! Would definitely rent again

Beautiful Tampa Bay Pool Home Near Gulf Beaches
Wonderful home and host, we had a great stay!

Sunny's Retreat
Great place to stay on a family vacation. Lots of restaurants in the surrounding areas. Home was very welcoming and the owners were very nice and responsive to any and all questions we had. Patio area was very nice and accommodating. Host was very nice and stayed in contact with me the entire trip. They were also willing to take care of a small issue with no hesitation and that speaks volumes to their willingness to help make sure their guests have an amazing experience. We look forward to our next trip! Thank you.

Private pool, Golf Cart, Completely Renovated!
We had a wonderful stay! The house was very clean and had everything we needed for the beach and pool. The golf cart was an amazing addition as there are many places to eat in driving distance to the house. Jarrett was very responsive and friendly. Would absolutely stay here again!

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens
Beautiful house and pool area. The back is private with plenty of space. Jeff was always responsive and everything was as described. The girls being able to get eggs every morning was an added touch of experience for them. The house was clean and we had everything we needed for the ten day stay. Tarpon Springs is an annual tradition and we weren't disappointed.

Tropical Getaway, Perfect Home & Great Location
If i could give 100 stars I would. This place is such a vibe. the house is absolutely stunning and they take care of you like you are family. There was coffee in the pantry, they have shampoo, conditioner and body wash if you want to use. The beds are very comfortable and the place is so clean. The outside was great for the kids. The house is located in a really good place close to everything. We felt like we were in our own home. Thank you so much for providing such a great experience for us.

Modern & Spacious Retreat with Private Pool!
Great stay! Honestly, I want to buy the house. Great location. Conveniently located close by Dunedin where Honeymoon Island is always a wonderful time, Clearwater and St. Pete. There's always something to do out and about when there's not, you have the pool, TONS of space, very nice bathrooms. You're even able to do your own laundry right there! I loved the office space especially, as I myself, am a real estate investor and being able to sit down at a desk and get some work done while the kids swim was VERY NICE. I'd stay here again 1000% Hopefully a couple more times before year's end...unless you guys want to sell it to me before then. :D

The T and C Club
Tom's place was perfect for our family. We especially loved the salt water pool and the pool table. Tom was very good at communicating everything clearly. He also has very friendly and helpful neighbors.
Weekly house rentals

Palm Harbor Renovated Hideaway!
Great location. A quick 35 min ride into Tampa or St Pete. Great host

Valencia Manor, your Favorite Florida Pool Home!
We had the best time at Jerzy’s place. Such a great place to stay, it really felt like home away from home. Really clean, had everything you could ever need, and a really nice pool. We loved the neighbourhood and the beaches, Honeymoon Island was especially nice. Jerzy is a great host, very easy to get a hold of. We would love to come back.

Beautiful in Tampa
It was a quick getaway for us, and we loved the place. It was a cozy, clean, and private place. Eduardo was very responsive and helpful.

Clearwater retreat: Luxury Spa & Comfort Stay
My family of 6 stayed at Brian's home for vacation. The accommodations were perfect. plenty of space, clean and decorated nicely. The backyard space was great to come home to after a day at the beach. Our family pet traveled with us as well. We felt as if it hit all of the high points we were looking for. Great place to stay. Centrally located for all the area beaches and a quick uber drive from St Pete airport. In a neighborhood that was quite and still had a very private feel to the outdoor spaces. Definitely would stay again!

Hatties Hill Florida
Susan is an amazing host! Extremely responsive, goes above and beyond for her guests. The place is very spacious, looks exactly like the photos and it feels like home. Very well equipped, it has everything one needs for short or long stays. The area offers great walks for those who want to keep active. Highly recommended if you are looking for a great place in Florida close to amazing beaches.

Luxe Retreat Paradise
Absolutely loved my stay at Anna’s house! The place was spotless, beautifully decorated, and felt extremely welcoming. I especially appreciated how private and peaceful it was—perfect for relaxing after a long day. Anna was a wonderful host and made everything easy. Highly recommend for anyone looking for a getaway!

Amazing Private Beach Home
The house is very spacious all appliances in the house are up to date. Beds were very comfy and plenty of outdoor seating for watching the wildlife that cruises the shore line. We got to see the dolphins cruising in the bay along with flamingos and egrets and the pelicans. Neighbors are quiet and keep to themselves. Drive into Clearwater is easy and quick. Well worth the stay for the family getaway

Townhouse in Clearwater
Joe was a great host, super communicative and available. His place was sparkling clean and close to everything I needed to do while there. Loved having the washer and dry and appreciated all the goodies he left throughout the house. I would absolutely stay again if I return the area. Thank you for everything!
Private house rentals

Nice Sparkling Clean Home with Pool.
Great host! Felt like home. Fantastic accommodations.

Renovated Centrally located w/ big fenced backyard
Great place and location! Easy check in and extremely easy checkout! Responsive host! Couldn’t ask for more!

The Coastal Calm - Entire Unit
This home had everything we needed for our first family beach trip! We stayed for a whole week and had plenty of included supplies. The home was even better than the photos! We look forward to our next visit here.

Tampa Retreat: Heated Salt Pool & Private Backyard
Grace was an excellent host! She was proactive and went above and beyond to make us feel at home. The house was adorable and comfortable. We were two moms with our daughters on a soccer trip and we felt safe and comfortable. I highly recommend Grace and her adorable home!

your home close to everything
Absolutely loved this booking! Alan was a great and responsive host. We had no issues the whole weekend and felt right at home. Will definitely be booking again :)

Lake Tarpon Waterfront-Private
Laura’s house was very nice and our family and dogs enjoyed staying there very much. It was extremely clean and recently updated. The neighborhood is very quiet and the canal location offered a nice place to view some wildlife. The beds were very comfortable and the kitchen is well stocked. Laura is quick to respond to any questions or information you need. Thank you Laura for sharing your get away and for allowing dogs too.

Nautical Landings - The Mainsail
Our family had a great time at this location. There is a lot to do either you want to have a relaxing time or to explore the area. The house was clean and everything was like new. We truly enjoyed our time here. The host was very attentive responding my questions right away. Highly recommended if you are looking for a great place with a lot to do!

3BR Waterfront House I Raymond James Stadium
Beautiful home. Exactly as described. Area was nice, close to everything we needed. Chelsea was a great host and responded within minutes. My parents enjoyed their stay. Would def stay again!!
Quick stats about house rentals in Oldsmar
Total rentals
90 properties
Nightly prices starting at
$38 SGD before taxes and fees
Total number of reviews
2.5K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
40 properties have a pool
Destinations to explore
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- Family-friendly rentals Oldsmar
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- Rentals with a washing machine and dryer Oldsmar
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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