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House holiday rentals in Oldsmar

Find and book unique houses on Airbnb

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Popular amenities for Oldsmar house rentals

House rentals with a pool

Top Guest favourite
Home in Port Richey
4.99 out of 5 average rating, 235 reviews

Heated & Screened in Pool-All Essentials Provided

TimRating, 5 stars1 week ago
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
Guest favourite
Home in Forest Hills
4.91 out of 5 average rating, 104 reviews

Private Pool 2BR/2B 3.5 mi Tarpon & Beaches

JessicaRating, 5 stars1 week ago
Clean place Prompt host Many amenities in the house
Top Guest favourite
Home in Dunedin
4.96 out of 5 average rating, 140 reviews

Dunedin 5 STAR! Heated POOL+10 Mins to Beach

ScottRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Tarpon Springs
4.96 out of 5 average rating, 362 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

DavidRating, 5 stars3 weeks ago
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.
Top Guest favourite
Home in Palm Harbor
4.95 out of 5 average rating, 149 reviews

Tropical Getaway w/Heated Pool & King Beds

JCRating, 5 stars4 days ago
I booked this AirBnb to stay there with my 3 kids, mom, and nephew. I work abroad and havent seen them in over a year. This airbnb and the surrounding area provided us with plenty to do and we achieved the goal of spending quality time together. Every day we would hit the beach and then when were in the house we would play games, watch movies, or swim. It was VERY relaxing with the quietness and beautiful scenery. Definitely worth the money for the memories we created. If youre on the fence about this place, book soon as possible or else you'll miss out.
Guest favourite
Home in Palm Harbor
4.95 out of 5 average rating, 120 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

IbnRating, 5 stars2 weeks ago
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.
Superhost
Home in Tampa
4.85 out of 5 average rating, 104 reviews

Luxurious House with private Pool.

CollinRating, 5 stars1 week ago
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.
Guest favourite
Home in Tampa
4.92 out of 5 average rating, 211 reviews

Rooms with a Pool

About1AriesRating, 5 stars3 weeks ago
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!!

Weekly house rentals

Top Guest favourite
Home in Palm Harbor
5 out of 5 average rating, 26 reviews

The Coastal Calm - Entire Unit

TracieRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Palm Harbor
4.88 out of 5 average rating, 24 reviews

Beachhouse Inspired Villa Close Honeymoon Island

KaitlynRating, 5 stars1 week ago
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!
Superhost
Home in Oldsmar
4.83 out of 5 average rating, 23 reviews

Sunny's Retreat

VanessaRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Tampa
4.93 out of 5 average rating, 58 reviews

Hermoso de en Tampa

NestorRating, 5 stars4 weeks ago
Excellent stay. For us the location was perfect. The place is nice and clean. The host is very friendly and helpful.
Superhost
Home in Tampa
4.93 out of 5 average rating, 27 reviews

The memories house

AmandaRating, 5 stars3 weeks ago
This was the cleanest place I have stayed. I had no issues.
Top Guest favourite
Home in Palm Harbor
4.98 out of 5 average rating, 45 reviews

Hatties Hill Florida

EmyRating, 5 stars8 months ago
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.
Superhost
Home in Oldsmar
4.86 out of 5 average rating, 92 reviews

Modern & Spacious Retreat with Private Pool!

AnnaRating, 5 stars2 weeks ago
The house was perfectly located from the airport, St Pete’s and Clearwater beach.
Guest favourite
Home in Tampa
4.85 out of 5 average rating, 26 reviews

Mari’s Cozy Getaway

AleighaRating, 5 stars3 weeks ago
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

Private house rentals

Guest favourite
Home in Safety Harbor
4.89 out of 5 average rating, 83 reviews

Nice Sparkling Clean Home with Pool.

ShendaRating, 5 stars2 weeks ago
Great host! Felt like home. Fantastic accommodations.
Guest favourite
Home in Tarpon Springs
4.96 out of 5 average rating, 80 reviews

Cozy, Quiet 2-Bedroom 2-Bath Downtown

MariaRating, 5 stars3 days ago
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!
Top Guest favourite
Home in Palm Harbor
4.94 out of 5 average rating, 66 reviews

Private pool, Golf Cart, Completely Renovated!

StephanieRating, 5 stars3 days ago
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!
Top Guest favourite
Home in Palm Harbor
5 out of 5 average rating, 61 reviews

Near Beach, Heated Pool, Backyard Games, Fire Pit

SharayahRating, 5 stars1 week ago
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!
Top Guest favourite
Home in Palm Harbor
4.98 out of 5 average rating, 42 reviews

Coastal cottage getaway! Beaches, Golf Cart Rental

JenniferRating, 5 stars1 day ago
We had a wonderful stay. House was clean and cozy. Would absolutely stay again. Neighborhood was clean and quiet.
Guest favourite
Home in Holiday
4.91 out of 5 average rating, 33 reviews

Simply Charming

AliciaRating, 5 stars1 day ago
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!
Top Guest favourite
Home in Clearwater
4.97 out of 5 average rating, 38 reviews

Casa Sea Belkis/Beach/Mini Golf/BBQ/Games/Bikes

JerryRating, 5 stars1 month ago
The house was clean and comfortable. The location was close to things we wanted to do so that was great. The neighborhood was quiet and peaceful. We communicated with our hosts using the app prior to our arrival but had no questions or problems after arrival so no need to communicate with them. We enjoyed our stay very much.
Top Guest favourite
Home in Allen's Ridge
5 out of 5 average rating, 29 reviews

Minutes from the Beach

StevenRating, 5 stars1 week ago
This place was awesome for a ton of reasons. We were in town from the East Coast because of the Metallica concert at Raymond James. I thought initially that it was too far away but the drive was seamless and was an added bonus being away from the busy downtown area. Quiet part of town but close to the beach. Great restaurants. The house was perfect. Stock fully with everything you would need in the kitchen. The house was older but the renovations looked great. Comfy beds. Pool was perfect. Great temp this time of year and little to no bugs. Provided beach chairs and it was great not to have to pack all those extra things. Host was proactive, provided great recommendations when asked. Overall this place was amazing and I would definitely stay here again.

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

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Oldsmar
  6. House rentals