
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.

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach
🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Casa Palmera! *Heated Pool!
Step into relaxation as you enter this tropical pool home, centrally located to everything one would need staying in Clearwater! This 4 bedroom, 2 bath home has been meticulously curated to give our guests the best experience imaginable during their stay on the west coast of Florida. Only 5 miles from world renown Clearwater Beach, 1 mile from the Phillies spring training site, less than 2 miles from some of the best local eateries in Safety Harbor and Dunedin. Come stay at Casa Palmera!

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.

Boho Oasis • Pool •Fire Pit • Near Beach & Airport
Welcome to my 3-bedroom, 2-bath Airbnb home in vibrant Tampa, Florida. BoHo Zen-style oasis, complete with a pool, BBQ area, and ping pong table, provides the perfect backdrop for your getaway. Just 15 minutes from the airport and the Bay Area. centrally located near major stores, convenience is at your doorstep.. Fully equipped kitchen and bedrooms are beautifully decorated, offering comfort and restful nights can't wait to host you and share this peaceful haven with you…😌☺️

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.

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.

Seasalt Breeze - Easy pool access, Free parking.
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

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!

Private apartment perfectly located in Citrus park
A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

Tropical Oasis Retreat w/ Heated Pool
Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

Private 1 Bed Apt with Pool and water front.
Hi, my name is Ivelise, and I’m happy to welcome you! I’m a friendly, respectful, and caring person who truly enjoys hosting and making guests feel comfortable and at home. I take pride in offering clean, peaceful, and well maintained space where you can relax after a long day.
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

Canal views, weekly and monthly Discounts

House of Relaxation

Dunedin 5 STAR+ Heated Pool+Near Beach

Tropical Getaway w/Heated Pool & King Beds

NEW Heated Salt Pool & Spa on Waterfront Canal

Coastal Escape: heated saltwater pool & playground
Condo rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

Relax in a Newly Renovated Beach Front Paradise

Very cozy quality place close to Clearwater Beach.

Lovely Condo minutes from beach & King bed

Bright and Spacious 1Bed/1Bath condo.

POOL VIEW IN A MODERN CONDO - Feel at Home

Modern Waterfront Condo - Captivating Sunset Views

SHEEK and Glam- heated pool Updated! 3 mi to beach
Other vacation rentals with a pool

Lake it easy

Wonderful Condo at Avalon - Fully Renovated

The Coastal Calm - Entire Unit

Valencia Manor, your Favorite Florida Pool Home!

Cozy Family Retreat, Tampa: Private Pool Oasis

Condo Conveniently located to Clearwater Beach

The Palm Haus • Heated Pool • Near Beach • Games

Heated pool, hot tub, game room, 10 min to beach
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ735 | ﺩ.ﺇ804 | ﺩ.ﺇ826 | ﺩ.ﺇ735 | ﺩ.ﺇ760 | ﺩ.ﺇ727 | ﺩ.ﺇ727 | ﺩ.ﺇ742 | ﺩ.ﺇ639 | ﺩ.ﺇ735 | ﺩ.ﺇ742 | ﺩ.ﺇ749 |
| 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 ﺩ.ﺇ73 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar vacation rentals include wi-fi access

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

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
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- Anna Maria Island
- Busch Gardens Tampa Bay
- Raymond James Stadium
- John's Pass
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Amalie Arena
- Anna Maria Public Beach
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- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- St Pete Beach
- Splash Harbour Water Park
- Busch Gardens
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- The Don CeSar
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