Holiday 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.

%{current} / %{total}1 / 1
Top Guest favourite
A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.
Home in Palm Harbor
5 out of 5 average rating, 126 reviews

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Superhost
A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.
Guesthouse in Palm Harbor
4.87 out of 5 average rating, 163 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

Superhost
A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.
Home in Tampa Heights
4.9 out of 5 average rating, 255 reviews

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

Guest favourite
The sleeping area features a cozy bed adorned with neutral-toned linens and decorative pillows. Three framed botanical prints are displayed on the wall above the bed. A bedside table with a lamp and a small potted plant is positioned next to the bed.
Apartment in Tampa
4.88 out of 5 average rating, 180 reviews

Private 1 Bed Apt with Pool and water front.

Enjoy the use of the onsite pool and Private 1-bedroom apartment in a peaceful waterfront community! Equipped with your own kitchenette and separate living area. Enjoy the serenity of swimming in your own pool on your vacation or relaxing work stay. Lounge chairs will make your stay even more relaxing. Close to the Veterans expressway and easy access to local restaurants, beaches, 10 minutes from the airport, 20 minutes from the river walk, and entertainment. This apartment is 300 square feet

Guest favourite
A screened-in pool area is featured, with a sparkling swimming pool shaped to enhance relaxation. Comfortable seating is arranged nearby, including lounge chairs and a shaded area. The inviting water reflects the blue sky above, with tropical plants adding a touch of greenery to the space.
Home in Safety Harbor
4.91 out of 5 average rating, 106 reviews

Modern Paradise home near Clearwater Dunedin Beach

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

Top Guest favourite
A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.
Home in Palm Harbor
4.99 out of 5 average rating, 144 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

Guest favourite
A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.
Home in Oldsmar
4.7 out of 5 average rating, 108 reviews

Private Pool Home Near Clearwater & Tampa

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

Top Guest favourite
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, 225 reviews

Rooms with a Pool

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

Top Guest favourite
A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.
Condo in Clearwater
4.99 out of 5 average rating, 142 reviews

Seasalt Breeze, by the pool, NO PETS

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

Top Guest favourite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 147 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Guest favourite
The exterior of a two-story condo building is featured, surrounded by tropical palm trees and well-maintained greenery. A paved walkway winds through the landscape, leading to the entrance of the building. The facade includes large windows, allowing natural light to fill the interiors.
Condo in Clearwater
4.87 out of 5 average rating, 130 reviews

Cozy 1 bedroom condo.

Enjoy Clearwater from this beautiful 700 SFT, 1 bedroom condo with year-round access to a heated pool and only a 15 minute drive from Clearwater Beach. 2nd story condo with a single flight of stairs not shared by any other apartments. Safe and quiet gated community. Gym next to the pool. Parking is unassigned with plenty of spots next to the buildings. Beach chairs, umbrella, towels, cooler and other items available for your use.

Guest favourite
A spacious living area is presented with a large grey sectional sofa adorned with various cushions. A wooden coffee table sits in front, with two ceiling fans above providing airflow. The open layout connects seamlessly to a modern kitchen visible in the background.
Home in Indian Rocks Beach
4.97 out of 5 average rating, 111 reviews

Dolphin Dreamer-6-Seat Golf Cart!

6-seater Lithium golf cart, BIG 75" TV, oversized queen over queen bunk bed, and 2 king beds. Dolphin Dreamer is the perfect beach house to get your toes in the water in under a two minute walk, the perfect beach community to walk to local cuisine, and the perfect beachy interior! Dolphin Dreamer is carefully planned out for families/groups that want to have fun together in the heart of an exciting beach community.

Popular amenities for Oldsmar rentals with a pool

When is the best time to visit Oldsmar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$306 AUD$335 AUD$344 AUD$306 AUD$316 AUD$303 AUD$303 AUD$309 AUD$266 AUD$306 AUD$309 AUD$312 AUD
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

Quick stats about holiday rentals with a pool in Oldsmar

  • Total holiday rentals

    Explore 80 holiday rentals in Oldsmar

  • Nightly prices starting at

    Oldsmar holiday rentals start at $31 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Oldsmar holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oldsmar rentals

  • 4.8 Average rating

    Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Oldsmar
  6. Rentals with pools