
Oldsmar Vacations from $574
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oldsmar Vacation
There's no better way to head off on a break than with one of our vacation packages to Oldsmar. The lively atmosphere and welcoming locals are just two of the countless reasons you'll want to visit this fascinating city. Eager to start exploring your surroundings? Big Cat Rescue, Westfield Citrus Park and Tampa Bay Downs are just three of the best places to visit during a trip to Oldsmar. No matter your travel plans or the size of your budget, organizing your ultimate tailored Oldsmar vacation is a walk in the park with Expedia.
The Latest Oldsmar vacation packages
Price found within the past 48 hours. Click for updated prices.




Crystal Palms Beach Resort
Sunshine Beach
Price was $1,251, price is now $795 per person
$795
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,409 reviews)
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating
Reviewed on Nov 7, 2026

Stay near popular Oldsmar attractions
What to do in Oldsmar

Starlite Infinity Evening Yacht Cruise Clearwater
$37
per adult
90% of travellers recommend

Clearwater Beach: Dolphin & Island Sandbar Cruise
$28
per adult
96% of travellers recommend

1.5-hour Dolphin Sightseeing Cruise from Tampa
$31
per adult
80% of travellers recommend
Oldsmar Hotel Deals

Courtyard by Marriott Tampa Oldsmar
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Nov 22 to Nov 23
$105 total
Nov 22 - Nov 23
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Not the courtyard experence you are expecting. Very limited and useless market, bistro and bar are closed,and overall you can tell they are suffering from lack of maintanem e and customers. For the price, I would not stay here again. At best they should be charging cheap motel or hotel pricing, for ..."
Reviewed on Nov 13, 2026

Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$240 nightly
The price is $271 total per night from Dec 13 to Dec 14
$271 total
Dec 13 - Dec 14
Total with taxes and fees

Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$267 nightly
The price is $301 total per night from Dec 8 to Dec 9
$301 total
Dec 8 - Dec 9
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Oldsmar Vacation Packages
Oldsmar Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tampa Intl. Airport (TPA) |
Population | 14,200 |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | ZooTampa at Lowry Park, Ben T. Davis Beach and Big Cat Rescue |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Hotels in Oldsmar
- Private Vacation Homes in Oldsmar
- Budget in Oldsmar
- Motel 6 Hotels in Oldsmar
- 4 Star Hotels in Oldsmar
- Pet Friendly in Oldsmar
- Hotels in Safety Harbor
- Bed and Breakfast in Safety Harbor
- Hilton Hotels in Oldsmar
- 5 Star Hotels in Oldsmar
- Aparthotels in Oldsmar
- Westchase Hotels
- Hotels in Dunedin
- Cottages in Safety Harbor
- Hotels in Palm Harbor
- Town 'n' Country Hotels
- Flights to Safety Harbor
- Flights from Philadelphia (PHL) to Clearwater (CLW)
- Delta Air Lines Atlanta (ATL) to Tampa (TPA) flights
- Flights to Oldsmar
- Flights from Tampa (TPA) to Clearwater (CLW)
- JetBlue Airways Jamaica (JFK) to Tampa (TPA) flights
- Flights to Dunedin
- Flights to Palm Harbor
- Flights to Tampa Intl.
- Flights to Clearwater
- Visit Palm Harbor
- Dunedin All Inclusive Vacation Packages
- Dunedin Vacations
- Where to stay in Oldsmar
- Visit Rocky Point
- Clearwater Vacations
- Caladesi Island State Park All Inclusive Vacation Packages
- Where to stay in Clearwater Beach
- Visit Downtown Dunedin
- Clearwater Beach Vacations
- Honeymoon Island State Park All Inclusive Vacation Packages
- Where to stay in Tampa
- Visit Tarpon Springs
- Pier 60 Park
- Keystone All Inclusive Vacation Packages
- Where to stay in Tarpon Springs
- Visit Clearwater
- Raymond James Stadium
- Clearwater Beach All Inclusive Vacation Packages
- Where to stay in Largo
- Visit Honeymoon Island State Park
- George M. Steinbrenner Field
- Tampa All Inclusive Vacation Packages
- Where to stay in Dunedin
- Beach Walk
- Tarpon Springs Vacations
- Tampa Vacations
- Palm Harbor Vacations
- Indian Rocks Beach Vacations
- Largo Vacations
- Downtown Tampa Vacations
- Madeira Beach Vacations
- Visit Town 'n' Country
- South Tampa All Inclusive Vacation Packages
- Where to stay in Indian Rocks Beach
- Visit Clearwater Beach
- Northwest Tampa All Inclusive Vacation Packages
- Where to stay in Northwest Tampa
- Visit Largo
- Honeymoon Island State Park All Inclusive Vacation Packages
- Where to stay in Caladesi Island State Park
- Visit Dunedin
- Clearwater-St. Pete Beaches All Inclusive Vacation Packages
- Where to stay in South Tampa
- Visit Ozona
- Things to do in Palm Harbor
- Things to do in Oldsmar
- Things to do in Clearwater
- Things to do in Tarpon Springs
- Things to do in Clearwater Beach
- Things to do in Dunedin
- Things to do in Largo
- Things to do in Tampa
- Things to do in Belleair Beach
- Things to do in Indian Rocks Beach
- Things to do in New Port Richey
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















