
Holiday rentals with a pool in Oldsmar
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oldsmar
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Oldsmar rentals with a pool
House rentals with a pool

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

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.

Private Pool 2BR/2B 3.5 mi Tarpon & Beaches
Absolutely loved this place. It was very comfortable and my kids loved the pool. The only negative was not being able to take a bath in the large jetted tub. There wasn’t a stopper provided to be able to fill the tub and relax in the bath. All else was amazing and my kids and I loved it!

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.

tu hogar cerca de todo
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 :)

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!

NEW Heated Salt Pool & Spa on Waterfront Canal
Great stay! Mark’s place was beautiful—exactly as pictured. The pool was stunning and right next to the river, which made for a peaceful and relaxing environment. Would definitely stay here again!
Apartment rentals with a pool

Seasalt Breeze private cozy unit
We had a good time. The apartment had everything you needed.

Very cozy quality condo close to Clearwater Beach
Marta is a pro host, she is attentive and quick to address any issues. Things happen and how those things are handled is what makes the difference between an ok experience and a great experience. I would absolutely stay at Marta's place again. Her place is equipped with all that you need to be comfortable and to feel right at home. The place is an excellent value!

Waterfront condo with sunset views of Tampa Bay.
We really enjoyed relaxing by the pool and having the Big Bamboo bar / restaurant on the premises made it so convenient. The bed was comfortable and shower pressure good. We also appreciated the coffee bar.

Bright and Spacious 1Bed/1Bath condo.
Daniel‘s condo was the perfect little stay for us. It is quiet and private. The people at the pool were so friendly. It’s one of the most comfortable beds in the world. We found a very nice authentic restaurant Mexican close by and shopping was within walking distance. The condo was neat and clean and had everything we needed.

Rocky Point paradise
It was a very clean place and a great location. We were there to attend an event at Raymond James which was only a short drive, and close enough to the beach to enjoy that as well. The balcony was nice and private. We loved being able to just sit and enjoy the peaceful water view!

Centrally Located/Pickleball/Pool/Washer/Dryer/Fun
Stayed for 2 nights with my wife and daughter. Condo was very clean and our bed was comfortable and my daughter said she slept well on drop down sleeper couch. Henrique was quick to respond to any questions and was super flexible for check in/out. If in Tampa area would stay again. Great clean place.

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES
The location was close to the places we attended for a wedding. Host was very informative and provided recommendations of places to go and things to do. We will be repeat guests.

POOL VIEW IN A MODERN CONDO - Feel at Home
We loved our stay! The hosts were great at communicating with us. Very clear instructions. Place was just like the photos. Very enjoyable stay!
Quick stats about holiday rentals with a pool in Oldsmar
Total rentals
70 properties
Nightly prices starting at
₹1,735 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
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
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- 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