
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.

Coastal Escape: heated saltwater pool & playground
★ 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

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.

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.

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.

Waterfront Pool Oasis •Kayak, Games & Sunset Views
Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

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.

Luxury Blue Haven - Stunning Tampa Bay Views!
Experience breathtaking waterfront views from your private balcony at Sailport Waterfront Suites, Tampa. This stunning 1BR/1BA condo is beautifully renovated and offers direct water views, providing the perfect balance of relaxation and adventure for you and your group. Enjoy easy access to exciting local attractions while indulging in the peace and tranquility of this desirable location. With an array of amenities, your stay is sure to be comfortable and memorable.

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, by the pool, NO hidden fees
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

NEW Heated Salt Pool & Spa on Waterfront Canal
🏠 Welcome to this incredible, stunning & fully updated heated pool & spa home located on a serene waterfront canal of Tampa Bay! Enjoy the dock for fishing & relaxing. Fast WIFI, Samsung Smart TVs, a game room with an air hockey table, ping pong & pool table, and even a Pac-Man machine will make your stay memorable & fun! Most importantly, dive into this amazing heated pool & spa right in front of the canal!

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.
Popular amenities for Oldsmar rentals with a pool
House rentals with a pool

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

NEW Cozy Family Retreat, Tampa: Private Pool Oasis

Canal views, dock, Manatees, pool and more

Dunedin 5 STAR+ Heated Pool+Near Beach

East Lake Gem On The Green

Luxury Clearwater Home • Heated Pool + Near Beach

The Palm Haus • Heated Pool • Near Beach • Games

Boaters Paradise- Waterfront Heated Pool King Beds
Condo rentals with a pool

Tampa Events & Suite w/WtrFrt Bay & Sunset Views

Tiki Themed Waterfront Condo on Tampa Bay

Tropical Waterfront Escape

Royal Orleans at Redington Beach ( Studio )

Rocky Point paradise

Amazing views on beachfront

Modern Waterfront Condo - Captivating Sunset Views

Waterfront condo on top floor @ Boca Ciega Resort
Other vacation rentals with a pool

Wonderful Condo at Avalon - Fully Renovated

Villa Luxe~Heated Saltwater Pool~Near Beaches

Relaxing home with palm trees & pool awaits you

Lovely Condo minutes from beach & King bed

Private pool, Golf Cart, Completely Renovated!

Private Coastal Getaway to Connect and Celebrate

Tampa Tropical-Saltwater Pool-10 Min to TPA

Casa St.George, Centrally Located, Pool, Game Room
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 80 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 1,930 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
80 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- House rentals Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a washer and dryer Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with beach access Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with a hot tub Oldsmar
- Hotel rooms Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Busch Gardens Tampa Bay
- John's Pass
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park
- Busch Gardens
- North Beach At Fort DeSoto Park
- Don CeSar Hotel




