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House vacation 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 favorite
A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.
Home in Port Richey
4.99 out of 5 average rating, 235 reviews

Heated & Screened in Pool-All Essentials Provided

TimRating, 5 stars5 days 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 favorite
A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.
Home in Holiday
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 favorite
A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.
Home in St. Petersburg
5 out of 5 average rating, 161 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

PatriciaRating, 5 stars1 week ago
This Airbnb was amazing! The house was clean and well organized. Ruta thought of everything from kitchen utensils and cookware to recreational games and equipment. There were plenty of chilled waters available to us in the refrigerator as well as extras in the garage refrigerator. The rooms are very spacious. The beds are extremely comfortable and complimented by multiple choices of pillows and blankets. The pool area is very nice with clean refreshing water and an intimate setting. There is plenty of living space to spread out as well as a game room with a pro-sized pool table. There is a variety of card games and even a poker set. Additionally a pack and play is provided by the host. I would definitely book this home again and will refer it to friends and family. Ruta really thought of everything.! 🤗🎊🥳🙌🏽
Top guest favorite
A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.
Home in Tarpon Springs
4.96 out of 5 average rating, 362 reviews

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

DavidRating, 5 stars2 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 favorite
A playground structure is shown with a slide and a small platform, set on green grass. Beyond the playground, a screened-in pool area is visible, with water reflecting the surrounding trees and sky. The tranquil backyard environment offers space for relaxation.
Home in Tampa
4.98 out of 5 average rating, 156 reviews

Tropical Getaway, Perfect Home & Great Location

AliciaRating, 5 stars3 weeks ago
Sure! Here’s a sample positive review you can use or customize: ⸻ I had a wonderful stay! The space was incredibly clean, well-maintained, and exactly as described in the listing. It felt cozy and comfortable from the moment I walked in. The host was also fantastic—very friendly, responsive, and made sure I had everything I needed for a smooth and enjoyable stay. I really appreciated the little thoughtful touches and the warm welcome. I would definitely stay again if I visit Tampa in the future. I highly recommend it to anyone looking for a clean, quiet, and pleasant place to stay!
Superhost
A private pool is surrounded by a spacious concrete deck, featuring several lounge chairs and tropical landscaping. The clear blue water is set against a backdrop of a blue sky and a white fence, creating an inviting outdoor retreat.
Home in Tampa
4.85 out of 5 average rating, 104 reviews

Luxurious House with private Pool.

CollinRating, 5 stars3 days 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 favorite
A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.
Home in Tampa
4.92 out of 5 average rating, 211 reviews

Rooms with a Pool

About1AriesRating, 5 stars2 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!!
Top guest favorite
A spacious swimming pool area is enclosed by large glass panels, allowing ample natural light. Two comfortable chairs are positioned beside a small table, offering a relaxing view of the clear water. The pool deck features patterned stone tiles, enhancing the area’s openness.
Home in Tampa
4.96 out of 5 average rating, 128 reviews

Welcome to villa marcelo

EvyrRating, 5 stars4 days ago
Our stay was wonderful! We needed ample space for a bachelorette vacay, and Franddy did not disappoint. Ample space, great amenities, super responsive and flexible. If you need a chill spot that’s not too far from attractions in Tampa, definitely recommend 100%

Weekly house rentals

Top guest favorite
A selection of woven storage baskets is displayed on a countertop, featuring neatly arranged napkins and two water bottles. A decorative sign reading 'HOME SWEET HOME' adds a personal touch to the arrangement, blending function with a welcoming aesthetic.
Home in Palm Harbor
5 out of 5 average rating, 12 reviews

Palm Harbor Renovated Hideaway!

CherisseRating, 5 stars2 weeks ago
Great location. A quick 35 min ride into Tampa or St Pete. Great host
Top guest favorite
A spacious living area features a large grey sectional sofa adorned with orange and blue accent pillows. A marble coffee table sits in front, while a ceiling fan is visible above. Light enters through large windows, illuminating the open layout connecting to a dining area.
Home in Palm Harbor
5 out of 5 average rating, 26 reviews

The Coastal Calm - Entire Unit

TracieRating, 5 stars2 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 favorite
A corner duplex villa is seen with a two-car garage and a welcoming entrance. Mature trees provide shade over the driveway, and a landscaped front yard features greenery along the home’s facade, creating a serene atmosphere.
Home in Palm Harbor
4.88 out of 5 average rating, 24 reviews

Beachhouse Inspired Villa Close Honeymoon Island

KaitlynRating, 5 stars3 days 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
A well-maintained exterior of a single-story home is surrounded by lush greenery and palm trees. A spacious driveway leads to the entrance, with a manicured lawn showcasing vibrant grass and tropical plants. The home's facade is light-colored, reflecting the sunny atmosphere.
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 favorite
A narrow outdoor space is lined by white fencing, featuring two black metal chairs with colorful cushions positioned on a gray brick path. Soft lighting is provided by string lights overhead, creating an inviting atmosphere. A small potted plant is situated between the chairs.
Home in Tampa
4.95 out of 5 average rating, 57 reviews

Beautiful in Tampa

NestorRating, 5 stars3 weeks ago
Excellent stay. For us the location was perfect. The place is nice and clean. The host is very friendly and helpful.
Superhost
The outdoor space features a heated pool surrounded by a smooth concrete deck. Several lounge chairs are positioned nearby for relaxation. Lush landscaping includes palm trees, and soft lighting adds ambiance to the area, creating an inviting environment for leisure.
Home in Oldsmar
4.86 out of 5 average rating, 91 reviews

Modern & Spacious Retreat with Private Pool!

MoriahRating, 5 stars3 weeks ago
Our stay was exactly as the pictures showed and more! Access to getting into the house was super easy and addressed ahead of time before arrival, and leaving was just as easy requiring little to no pick up, I would recommend this place to anyone. I would say the only downside was that one of the bathrooms made a squealing noise when toilets were being flushed, but it was something that was easy to block out after a while. Best stay we’ve had in a long time ! :)
Top guest favorite
The spacious living room is furnished with a light grey sofa and a pullout couch, accompanied by a modern coffee table. Natural light is welcomed through multiple windows, while a ceiling fan adds comfort. Artwork adorns the walls, creating an inviting ambiance.
Home in Palm Harbor
5 out of 5 average rating, 9 reviews

The Retreat at Palm Harbor - RV & Work-Friendly

DavidRating, 5 stars2 weeks ago
We enjoyed our week here! Pouria's home is in a great location on a quiet street. The king size bed was comfortable and we had plenty of space to spread out. The backyard is large and private. This was a perfect stay and we highly recommend this home if you're in the area.
Guest favorite
A well-appointed sleeping area showcases a spacious bed with neutral bedding and decorative pillows. A bright yellow accent chair enhances the room, while a mirror reflects the stylish decor. Vertical blinds allow natural light to filter in, creating a warm ambiance.
Home in Tampa
4.85 out of 5 average rating, 26 reviews

Mari’s Cozy Getaway

AleighaRating, 5 stars2 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

Superhost
A spacious sleeping area features a dark bedframe with a decorative blue and white patterned comforter. A well-equipped kitchenette is visible, showcasing modern appliances and a stylish bar area with two stools. Natural light illuminates the room, highlighting clean, neutral tones.
Home in Tampa
4.69 out of 5 average rating, 230 reviews

Tampa Bay Cozy apartment

JoniusRating, 5 stars3 weeks ago
Great place will definitely stay here again and very friendly and peaceful definitely a place I will recommend
Guest favorite
The exterior of a single-story house is presented, featuring a two-car garage and a well-maintained lawn. Lush green shrubs frame the entrance, and a small American flag is placed near the mailbox. A partly cloudy sky adds depth to the welcoming scene.
Home in Safety Harbor
4.89 out of 5 average rating, 82 reviews

Nice Sparkling Clean Home with Pool.

KalinRating, 5 stars2 weeks ago
Stayed here two years in a row, both times me and my family enjoyed every minute of our stay!
Top guest favorite
An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.
Home in Palm Harbor
4.94 out of 5 average rating, 64 reviews

Private pool, Golf Cart, Completely Renovated!

JamesRating, 5 stars4 days ago
This home is beautiful decorated. Comfortable. It is our 2nd time staying in 2025. We love the location. We especially love having full access to the golf cart to go to many of our favorite restaurants. The pool is beautiful. 4 of us stay here and we will return again when we are in the area. It is central to all the places we love to go. Jarrett is a great and responsive host.
Guest favorite
A dining area is featured with a dark wooden table surrounded by four light-colored chairs. A large artwork depicting a beach scene is mounted on the wall, complemented by ambient lighting. Doorways leading to other rooms are visible, enhancing the space's openness.
Home in Tampa
4.89 out of 5 average rating, 37 reviews

your home close to everything

KellieRating, 5 stars1 week ago
Great place, pool was very nice. Rooms were nice. We stayed with our young kids and there weren’t plastic plates/ cups, but they were careful with the glassware. Fridge was very updated and nice as well as tvs in all the rooms and living room. Great lounging couch. Overall we would stay again.
Top guest favorite
A cozy living area showcases a vibrant green couch paired with a wooden coffee table. A wall of bookshelves filled with colorful books serves as a backdrop, while decorative items are placed on a shelf above. Bright patterned area rugs and light from the window enhance the space.
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.
Top guest favorite
An open-concept living area is visible, featuring a light-colored sectional sofa and a large flat-screen television mounted on the wall. A dining table sits to one side, next to a modern kitchen with stainless steel appliances and a spacious island. Large windows provide views of the outdoor space.
Home in Palm Harbor
5 out of 5 average rating, 28 reviews

Minutes from the Beach

StevenRating, 5 stars2 days 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.
Guest favorite
A modern kitchen area is visible, featuring stainless steel appliances and a light wood dining table. Soft teal tiles create a refreshing backsplash behind the stove, with ample storage and preparation space. The adjoining living area includes a comfortable sofa, mounted television, and large windows allowing natural light.
Home in Palm Harbor
4.98 out of 5 average rating, 57 reviews

Oasis near beaches & golf courses-Fire pit & bikes

AlexisRating, 5 stars3 days ago
Great place. Very kid friendly. Loved the location which was close to downtown Palm Harbor and only 10 minutes from the beach! Would highly recommend!
Superhost
The exterior view of the home reveals a spacious backyard, framed by lush green grass and shaded by trees. A screened-in pool area is visible, providing a safe and inviting space for relaxation and recreation.
Home in Oldsmar
5 out of 5 average rating, 6 reviews

Shore Drive Sunshine

NicoleRating, 5 stars1 month ago
Melody was so friendly and responsive throughout our entire stay. We’re Tampa locals and stayed here while our house was renovated, and let’s just say, we felt right at home! This was one of the most organized and clean Airbnbs I’ve ever stayed at. Everything was labeled and easy to find throughout the house. It was a great experience for our family. I would highly recommend staying here!

Quick stats about house rentals in Oldsmar

  • Total rentals

    90 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 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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  4. Pinellas County
  5. Oldsmar
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