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House holiday rentals in Oldsmar

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Popular amenities for house rentals in Oldsmar

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 stars2 weeks 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
Top guest favourite
Home in St. Petersburg
5 out of 5 average rating, 163 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

AriannaRating, 5 stars2 days ago
Wonderful home and host, we had a great stay!
Superhost
Home in Oldsmar
4.83 out of 5 average rating, 23 reviews

Sunny's Retreat

VanessaRating, 5 stars4 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 Palm Harbor
4.94 out of 5 average rating, 66 reviews

Private pool, Golf Cart, Completely Renovated!

StephanieRating, 5 stars1 week 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 Tarpon Springs
4.96 out of 5 average rating, 363 reviews

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

DavidRating, 5 stars1 week ago
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.
Top guest favourite
Home in Tampa
4.98 out of 5 average rating, 159 reviews

Tropical Getaway, Perfect Home & Great Location

MillenaRating, 5 stars1 week ago
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.
Superhost
Home in Oldsmar
4.86 out of 5 average rating, 93 reviews

Modern & Spacious Retreat with Private Pool!

KieferRating, 5 stars1 week ago
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
Top guest favourite
Home in Tampa
4.98 out of 5 average rating, 159 reviews

The T and C Club

MonicaRating, 5 stars2 weeks ago
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

Top guest favourite
Home in Palm Harbor
5 out of 5 average rating, 12 reviews

Palm Harbor Renovated Hideaway!

CherisseRating, 5 stars4 weeks ago
Great location. A quick 35 min ride into Tampa or St Pete. Great host
Superhost
Home in Palm Harbor
4.85 out of 5 average rating, 61 reviews

Valencia Manor, your Favorite Florida Pool Home!

RikkeRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Tampa
4.93 out of 5 average rating, 60 reviews

Beautiful in Tampa

MyaiRating, 5 stars2 days ago
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.
Top guest favourite
Home in Clearwater
5 out of 5 average rating, 63 reviews

Clearwater retreat: Luxury Spa & Comfort Stay

LauraRating, 5 stars3 days ago
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!
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 Palm Harbor
5 out of 5 average rating, 3 reviews

Luxe Retreat Paradise

JoshRating, 5 stars1 week ago
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!
Guest favourite
Home in Oldsmar
4.93 out of 5 average rating, 57 reviews

Amazing Private Beach Home

AngelineRating, 5 stars1 week ago
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
Top guest favourite
Home in Clearwater
5 out of 5 average rating, 20 reviews

Townhouse in Clearwater

FranRating, 5 stars4 months ago
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

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

Nice Sparkling Clean Home with Pool.

ShendaRating, 5 stars3 weeks ago
Great host! Felt like home. Fantastic accommodations.
Superhost
Home in Palm Harbor
4.92 out of 5 average rating, 25 reviews

Renovated Centrally located w/ big fenced backyard

AmirRating, 5 stars1 month ago
Great place and location! Easy check in and extremely easy checkout! Responsive host! Couldn’t ask for more!
Guest favourite
Home in Palm Harbor
4.96 out of 5 average rating, 27 reviews

The Coastal Calm - Entire Unit

TracieRating, 5 stars1 month 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.
Top guest favourite
Home in Tampa
4.98 out of 5 average rating, 65 reviews

Tampa Retreat: Heated Salt Pool & Private Backyard

AshleyRating, 5 stars1 week ago
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!
Guest favourite
Home in Tampa
4.85 out of 5 average rating, 41 reviews

your home close to everything

sofiaRating, 5 stars1 week ago
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 :)
Top guest favourite
Home in Palm Harbor
5 out of 5 average rating, 13 reviews

Lake Tarpon Waterfront-Private

KarenRating, 5 stars1 week ago
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.
Superhost
Home in Palm Harbor
New place to stay

Nautical Landings - The Mainsail

WaleskaRating, 5 stars1 week ago
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!
Superhost
Home in Tampa
4.95 out of 5 average rating, 40 reviews

3BR Waterfront House I Raymond James Stadium

LorenaRating, 5 stars9 months ago
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

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