
Vacation 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.

Lovely Condo minutes from beach & King bed
Kick back and relax in this calm, stylish space.Minutes away from Clearwater Famous Beach.You will be pleased with high ceilings and open floor plan.King size bed in the Bedroom with balcony and 55" smart Tv. Walk-in closet and updated bathroom. Spacious covered patio style balcony. Full-size washer and dryer inside the unit. Fully updated and equipped kitchen. Specious living room with a sleeper sofa that can sleep two quests and 65"smart Tv. Heated outdoor pool, gym, fast wifi internet, cable

The T and C Club
Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you wonāt want to leave!

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.

Dunedin 5 STAR+ Heated Pool+Near Beach
This Modern Coastal home is the perfect vacation spot! Recently renovated 3br home located just a few minutes from downtown Dunedin and some of the best Gulf Coast beaches. Take a dip in our heated saltwater pool, or relax on the screened-in patio with a cup of coffee. The open concept design creates a relaxing atmosphere with all the necessary amenities. Conveniently located near excellent dining options, shopping, Blue Jays stadium, and the waterfront. Make unforgettable memories.

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.

Private pool, steps to gulf, fishing, bike trails
Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

Gulf-View 2BR/2BA Beach Condo!
This Indian Rocks Beach Gulf Front Hamilton House building is located directly on unique Clearwater- St.Pete white sand beach with private beach access and heated pool, washer and drier in the unit. Our 3rd floor 1100 sq. feet 2 bedroom condo #207 offers a spacious balcony bordered with palm trees with northerly nice side view of the Gulf of Mexico and white sand beach that goes on for miles. Two assigned parking spaces (one under the building and second uncovered).

Tropical Paradise
Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

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.

Ocean Breeze ⢠Easy - Heated Pool Access
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and itās 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

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

Literally: 15 steps to the Pool, GroundFloor Condo
Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!
Popular amenities for Oldsmar rentals with a pool
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Heated Pool, 10 min to Beach, Close to Restaurants

Villa Paradise

Pet-friendly Beach Home with Heated Pool & Spa

The Palm Haus ⢠Heated Pool ⢠Near Beach ⢠Games

NEW Heated Salt Pool & Spa on Waterfront Canal

Entire residential home, Tampa. 3/2, Pool.

FREE Heated Pool & Spa l Book your Winter Vacation
Condo rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Amazing main floor condo at Avalon

Bright and Spacious 1Bed/1Bath condo.

Tropical Beachfront Penthouse-Beach Cottages

Spectacular beach to bay views from this resort.

Royal Orleans at Redington Beach ( Studio 203 )

Modern Waterfront Condo - Captivating Sunset Views
Other vacation rentals with a pool

Wonderful Condo at Avalon - Fully Renovated

The Coastal Calm - Entire Unit

Valencia Manor, your Favorite Florida Pool Home!

Condo Conveniently located to Clearwater Beach

Heated pool, hot tub, game room, 10 min to beach

Relaxing Retreat Near Clearwater Beach

2 Bed 2 Bath Remodeled House Palm Harbor

ā¤Amazing Waterfront View/Near Downtown& Airport āš¬
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $273 CAD | $299 CAD | $307 CAD | $273 CAD | $282 CAD | $270 CAD | $270 CAD | $276 CAD | $237 CAD | $267 CAD | $277 CAD | $273 CAD |
| Avg. temp | 17 °C | 18 °C | 20 °C | 23 °C | 26 °C | 28 °C | 29 °C | 29 °C | 28 °C | 25 °C | 21 °C | 18 °C |
Quick stats about vacation rentals with a pool in Oldsmar

Total vacation rentals
Explore 90 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at $27Ā CAD per night before taxes and fees

Verified guest reviews
Over 1,870 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
90 of Oldsmar vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guestsāaveraging 4.8 out of 5!
Destinations to explore
- SeminoleĀ Vacation rentals
- Central FloridaĀ Vacation rentals
- MiamiĀ Vacation rentals
- St Johns RiverĀ Vacation rentals
- OrlandoĀ Vacation rentals
- Gold CoastĀ Vacation rentals
- Miami BeachĀ Vacation rentals
- Fort LauderdaleĀ Vacation rentals
- TampaĀ Vacation rentals
- Four CornersĀ Vacation rentals
- KissimmeeĀ Vacation rentals
- Key WestĀ Vacation rentals
- Fitness-friendly rentalsĀ Oldsmar
- Rentals with a hot tubĀ Oldsmar
- Hotel roomsĀ Oldsmar
- Rentals with a firepitĀ Oldsmar
- Pet-friendly rentalsĀ Oldsmar
- Family-friendly rentalsĀ Oldsmar
- Rentals with a fireplaceĀ Oldsmar
- Rentals with beach accessĀ Oldsmar
- Waterfront rentalsĀ Oldsmar
- Rentals with outdoor seatingĀ Oldsmar
- House rentalsĀ Oldsmar
- Rentals with a washer and dryerĀ Oldsmar
- Rentals with a patioĀ Oldsmar
- Rentals with poolsĀ Pinellas County
- Rentals with poolsĀ Florida
- Rentals with poolsĀ United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Dunedin Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island
- Busch Gardens
- The Don CeSar
- Gulfport Beach Recreation Area
- Lakewood National Golf Club




