
Vacation 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.
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Popular amenities for Oldsmar rentals with a pool
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

Near Beach, Heated Pool, Backyard Games, Fire Pit
Karolina was a wonderful host and was quick to respond to any inquiries we had. The home exceeded our expectations. It was beautifully decorated, CLEAN (a huge plus for us), well stocked with everything we needed, and more! The grounds were beautifully landscaped, which made spending time outdoors even more enjoyable. We especially loved spending time by the pool and in the game room. We all loved how comfortable the beds were. Karolina has created a space that is warm, inviting, comfortable, tranquil, and fun. It truly felt like home away from home. We hope to come back one day!

Clearwater retreat: Luxury Spa & Comfort Stay
Had a great stay at Brian’s place! The home was spotless, comfortable, and exactly as described. Check-in was smooth, communication was clear and responsive, and the kitchen was well-stocked with everything we needed. The guidebook was a nice touch and helped us explore the area. Highly recommend and would definitely stay again!

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens
Overall our stay was great! Jeff was very responsive, and left us a lot of recommendations for local restaurants. The house was very clean and the pictures accurately reflected how to house looked. The only downsides were the large bugs that somehow got in the home. There were 3 occasions this happend but they seemed harmless. The net around the pool had a tear in it allowing spiders and lizards inside of the pool area but they stayed around the outside of the pool so we could avoid them.

tu hogar cerca de todo
Such an amazing stay with an even more incredible host Alan was always available to answer all our questions made great suggestions for local restaurants A definite must stay again next time we are in Tampa

Luxurious House with private Pool.
The house was perfect for my wife, my dad, my good friend, and myself for the Metallica weekend. I have season tickets for the Bucs, but typically make the 2hr drive back home. Now we have a place to go back to for an extended trip. The pool is great! The house was clean and as advertised. If you are heading to either Raymond James Stadium or Steinbrenner Field, it's about a 15 minute drive depending on traffic. We will definitely be back.

Rooms with a Pool
my husband and I took our 3 kids here for memorial day weekend. the house in a nice quiet and clean neighborhood which we loved. we only had one problem when we arrived which was the AC was out and in Florida that can be a huge problem. but we let the host know right away and they called someone to fix it. we cooled off in their beautiful pool until it was fixed and before we went to bed we had a cool house. so thank you for your prompt response in getting that fixed. other than that the house is truly a gem. very clean, great amenities and the guidebook was a wonderful addition! my kids really enjoyed the pool and hot tub and the place is very spacious where we had our room. they pretty much had everything you could think of product wise so we didn't need to get much for our stay. we are from Florida but we don't visit Tampa often but this is a place we know we will come to visit again for sure!!! thank you Aaron and Sophie for making my family vacay and wonderful one!!

Angelita's Lake Home 3br3ba w/heated pool
I’ve stayed at a lot of airbnbs but this is probably the best one so far! The place was spotless. They had everything you needed. Comfortable furniture and beds. Definitely not cheap IKEA stuff. The pool was amazing and spotless. Floats were very clean. Outdoor dining furniture was very nice. So pretty at night with all the solar lights. Close to Tarpin Springs and Tampa. What really topped it off was there wasn’t 2 hours of work we had to do to check out! This place is amazing! 6 stars.
Condo rentals with a pool

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.

Seasalt Breeze private cozy unit
Beautiful, very clean condo, very clean pool. Great location only a short drive to Clearwater beach. Margaret was very responsive to our questions and was an excellent host. Would highly recommend staying at this location.

Very cozy quality condo close to Clearwater Beach
The condo was wonderful - spacious, spotless and super quiet which made for a relaxing stay. I liked having a washer and dryer, dishwasher and beach supplies. Marta was a thoughtful and responsive host who checked in on me during my stay, which I appreciated.

Lakeside 2- Bed Apartment Near Clearwater Beaches
Beautiful condo. Comfortable beds. Great restaurants near by. Beautiful beaches near by. The swimming pool was clean and the kids really enjoyed it. Would definitely stay again.

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!

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views
Great area. Great view. Awesome pool/ bar area!

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Airbnb has anything you might have forgot. Henrique was very responsive. Changed out an air filter to help with my allergies. Would stay again.
Quick stats about vacation rentals with a pool in Oldsmar
Total rentals
70 properties
Nightly prices starting at
G$4,183 GYD 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
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
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- 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