Oldsmar Vacation Packages
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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.
Top Oldsmar Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,738
per person
Nov 25 - Nov 30
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
Very clean place, great staff but had bathroom issues which they will fix! But overall good.
Reviewed on Oct 16, 2026
Anna Maria Beach Resort
CA $4,670
per person
Nov 24 - Nov 29
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (423 reviews)
We loved the Anna Maria Beach Resort and plan on returning for another vacation!
Reviewed on Oct 15, 2026
Sunrise Garden Resort
CA $2,203
per person
Nov 24 - Nov 29
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
4/10 (2 reviews)
The hotel was conveniently located near the beach and restaurants. The interior and exterior were immaculately clean, and the pool was a lovely feature. It was a peaceful and relaxing getaway.
Reviewed on Oct 15, 2026
Ready to book your vacation to Oldsmar?
Oldsmar Hotel Deals
Courtyard by Marriott Tampa Oldsmar
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
CA $139
CA $157 total
Oct 19 - Oct 20
includes taxes & fees
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $291
CA $385 total
Oct 28 - Oct 29
includes taxes & fees
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $337
CA $437 total
Oct 18 - Oct 19
includes taxes & 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.
Stay near popular Oldsmar attractions
Oldsmar Flea Market
8.2/10 (64 reviews)
You can find the perfect gifts to bring home at Oldsmar Flea Market during your stay in Oldsmar. Stroll along the beautiful beaches or attend a sporting event in this family-friendly area.
beach near Veterans Memorial Park
Why not spend a lazy afternoon at beach near Veterans Memorial Park during your trip to Oldsmar? While in this family-friendly area, you can savor the top-notch restaurants.
What to do in Oldsmar
Starlite Infinity Evening Yacht Cruise Clearwater
CA $51
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $39
per adult
94% of travellers recommend
Tarpon Springs: Evening Dolphin Cruise
CA $40
per adult
100% of travellers recommend
Frequently asked questions
How much does an Oldsmar vacation package cost?
You can snap up a vacation package to this top destination from CA $1,676 on Expedia. However, how much your vacation to Oldsmar costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Oldsmar?
If you're looking to book a cheap Oldsmar vacation package, consider planning a trip in September, October and November. You're likely to find better rates on hotels and airfares during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Oldsmar?
Oldsmar vacations can be short or long, but to get a true feel for this place, we reckon 2 days is about right. With this timeframe, you can fit in top sights like Westchase Golf Course and Oldsmar Flea Market and seek out some hidden gems. Don't miss out on neighbourhoods such as Timberlane Woodlake and Tampa Shores either. If you plan wisely, you may even be able to take a day trip from Oldsmar too.
Is it worth booking a vacation package to Oldsmar?
During your Oldsmar vacation, you can count on experiencing some excellent nature and history. Leave enough time in your itinerary to visit major attractions like Oldsmar Flea Market and Oldsmar Historical Society Museum.
How to find the best Oldsmar package deals?
Use Expedia's filters to help you find some fabulous Oldsmar package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Oldsmar package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book an Oldsmar vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still have the freedom to create a tailored Oldsmar vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Oldsmar?
If you have your Oldsmar travel dates finalized, book early to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Oldsmar?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Oldsmar.
- Plan your budget wisely: On top of the price of your stay, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may come up during your trip to Oldsmar.
- Decide how many days away: Start by compiling a list of the attractions and activities you'd like to get to in Oldsmar. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Oldsmar vacation package.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
