
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 Oldsmar house rentals
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

Private Pool 2BR/2B 3.5 mi Tarpon & Beaches
Clean place Prompt host Many amenities in the house

Beautiful Tampa Bay Pool Home Near Gulf Beaches
We had a great time at Ruta’s airbnb. She was always very quick to respond when we needed anything which was greatly appreciated. She has everything you would need at her airbnb and she gave us great recommendations.

Dunedin 5 STAR! Heated POOL+10 Mins to Beach
Great place! We were in town for a baseball tournament and it was the perfect location close the the Blue Jays Spring Training facility. Close to the beach and lots of restaurants. The house was very clean and had everything we needed for our stay. We will definitely book here 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.

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr
We visited for my son's graduation. The house accommodated us very well. Spacious, clean, plenty of towels. The pool, grill, and fire pit was a plus.

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!!

Tropical Pool Retreat in Tarpon Springs
It's our second stay at this house. Great location and nice place with a pool. We bring jet ski and able to use the garage, which makes it very convenient. Kids and wife love it. Howard beach and Sunset beach only 5 minutes down the street. Tarpon Springs has good bakery, seafood and pizza joint, all of which just a couple of miles away. Honeymoon beach is also close if you like more of a beachy feel. Overall, we love the area and will come back next year for another week.
Weekly house rentals

Beachhouse Inspired Villa Close Honeymoon Island
First off I’d like to say that Sophia and Andrew were exceptional hosts. Unfortunately we got in really late and Sophia was still available to help with our check-in! The place was beautiful and perfect for our stay, clean, tidy, quiet and roomful. We brought our 2 doggies and the fenced in backyard was perfect for them. Very unique to see a piano, and a record player (which we definitely used.) All in all we would 100% stay again and recommend anyone looking in the area to book!

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.

Cozy, Quiet 2-Bedroom 2-Bath Downtown
Sean's place is such a pleasant place, very comfortable, clean, well located We're happy staying there. It was a short time but we're able to do some of the sightseeing the town offers We had been in Greece two years ago, the chance of visiting again is remote, so Tarpon Springs brought us some good memories of the wonderful trip we had once. Thank you Sean, Sarah and Shannon!

Beautiful in Tampa
Excellent stay. For us the location was perfect. The place is nice and clean. The host is very friendly and helpful.

The memories house
This was the cleanest place I have stayed. I had no issues.

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.

Mari’s Cozy Getaway
I had a great stay, definitely quiet! Would stay here again, was very close too where I needed too go and everywhere was 7-10 minutes away! Definitely recommend

Newly Listed & Beautifully Renovated Studio Condo.
Myrele was wonderful to communicate with, and even offered me an early check in and late check out. Place was modern and clean and super quiet. Definitely would stay In Myrele condo again.
Private house rentals

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.

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.

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!

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!

your home close to everything
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

Simply Charming
We came in town for a baby shower and this place was perfect! It was as described and very comfortable! Would definitely stay here again if we have to come back down to Florida!

The Weekender- Lake Access, Bikes, Outdoor Living
This place was absolutely amazing. From the moment I walked in, the house was clean and welcoming. Everything I needed was exactly where Kimberleigh said it would be. Kimberleigh has everything you could possibly need, from make up remover wipes to hair ties and straighteners in case you forgot your own. The home was sparkling clean and quite comfortable, with extra throw blankets and pillows. Every detail you can think of for a peaceful getaway has been executed. Kimberleigh, thank you for the clear communication and quick responses to everything and having such a beautiful getaway spot you’re willing to share with the world. I didn’t want to leave but I will certainly be back.
Quick stats about house rentals in Oldsmar
Total rentals
90 properties
Nightly prices starting at
$46 AUD 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
- Rentals with a washing machine and dryer Oldsmar
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- Rentals with pools Oldsmar
- Pet-friendly rentals 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