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.
Hibiscus Suites - Gateway to Siesta Key
CA $831
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.6/10 Excellent! (2,434 reviews)
The room and property were clean but they need to fumigate. I understand it’s Florida so I will still give them a 4 star. The bed and pillows were not that comfortable. Bed was very hard and pillows way too thick.
Reviewed on Sep 14, 2026
voco Sarasota by IHG
Central Sarasota
CA $1,325
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,004 reviews)
The hotel is well-located, and well-maintained. The room was clean and spacious. I took advantage of the hotel's relatively small pool, which was fine. The dining area was being renovated, and was only open on weekends (I chose not to dine there). I did not take advantage of the hotel's shuttle to beaches and other nearby amenities. Hotel staff are well-trained and very accommodating. The hotel is walking distance from the commercial area of the downtown, and there are numerous restaurants to choose from. Hotel management, according to staff upon my checkout, apparently would have been gracious in offering to reduce and refund my prepaid reservation by one night of my four night stay due to my airline's extremely delayed plane departure causing a missed airplane connection (and thus a forced overnight stay at the connecting city instead of my reserved day of initial arrival at voco Sarasota). But unfortunately Hotels.Com was unwilling to accommodate my request for the one-night refund.
Reviewed on Sep 13, 2026
Ready to book your vacation to Oldsmar?
Oldsmar Hotel Deals
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
3990 Tampa Rd Oldsmar FL
Fully refundable
CA $135
CA $152 total
Sep 30 - Oct 1
includes taxes & fees
9.4/10 Exceptional! (1,399 reviews)
"All was good except the bed and pillows. The bed was too low, and both bed and pillows were too soft"
Reviewed on Sep 13, 2026
Courtyard by Marriott Tampa Oldsmar
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
CA $130
CA $147 total
Sep 20 - Sep 21
includes taxes & fees
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
CA $215
CA $244 total
Sep 17 - Sep 18
includes taxes & fees
8.6/10 Excellent! (1,578 reviews)
"E"
Reviewed on Sep 13, 2026
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
Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $39
per adult
96% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
CA $51
per adult
90% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
CA $51
per adult
96% 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 $831 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.
