Oldsmar Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Oldsmar

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
The price is S$228 per night from 29 Aug to 30 Aug
S$228
29 Aug - 30 Aug
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Overall, it was a great place to stay, clean, comfortable, parking garage, private Bay access, jet ski rentals, Starbucks in the lobby, and nice staff. Things to note - hotel is right by interstate so you can hear traffic/cars, there is no pool available, or an outdoor shower. They currently have ..."

Reviewed on 5 Aug, 2025

The Westin Tampa Bay
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is S$292 per night from 10 Aug to 11 Aug
S$292
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Place was clean and nice !"

Reviewed on 7 Aug, 2025

Grand Hyatt Tampa Bay
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is S$284 per night from 18 Aug to 19 Aug
S$284
18 Aug - 19 Aug
includes taxes & fees
8/10 Very Good! (2,095 reviews)
"Great location"

Reviewed on 8 Aug, 2025

Hilton Clearwater Beach Resort & Spa
See all 15,152 properties in Oldsmar
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.

Popular places to visit

Raymond James Stadium

Raymond James Stadium

Catch an event at Raymond James Stadium during your trip to Tampa. Attend a football match or simply enjoy the top-notch restaurants while you're in the area.

Raymond James Stadium
Florida Aquarium featuring modern architecture and marine life

Florida Aquarium

Embark on a colorful exploration of Florida’s ecosystems and aquatic habitats at this popular aquarium.

Florida Aquarium
Lowry Park Zoo which includes a park, zoo animals and land animals

ZooTampa at Lowry Park

Hands-on animal activities, a manatee hospital and children’s rides are among the top attractions at this popular animal park.

ZooTampa at Lowry Park

What to do in Oldsmar

Self-Guided Driving Bundle of Florida Tours

Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle

S$51
per traveller
100% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
Step into the shadows and discover the haunting tales of our city's past.

Tampa Terrors Ghost Tour By US Ghost Adventures

S$33
per adult
100% of travellers recommend
Tampa Terrors Ghost Tour By US Ghost Adventures
Tampa Bar Crawl

Tampa Bar Crawl on a 2023 Street Legal Golf Cart

S$46
per adult
100% of travellers recommend
Tampa Bar Crawl on a 2023 Street Legal Golf Cart
See all activities in Oldsmar

Frequently asked questions

How much does an Oldsmar holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Oldsmar costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Oldsmar?
If you're looking to snag a cheap Oldsmar holiday package, consider visiting in September, October and November. You'll generally find lower rates on flights and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Oldsmar?
With a well-organised travel plan, you can easily tick off the most popular Oldsmar attractions in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Oldsmar holiday for longer.
Is it worth booking a holiday package to Oldsmar?
Whether you're planning to visit attractions like Oldsmar Flea Market and Oldsmar Historical Society Museum, or want to experience its top-notch nature and history, an Oldsmar holiday guarantees an unforgettable adventure. Book your trip with Expedia and discover why Oldsmar is such a good holiday destination.
How to find the best Oldsmar package deals?
Start your search for an Oldsmar package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Oldsmar package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oldsmar getaway off to a flying start.
Is it cheaper to book an Oldsmar holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging stays and flights separately. Better still, you can tailor your Oldsmar getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Oldsmar?
If you've got your Oldsmar travel dates locked in, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Oldsmar?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Oldsmar.
  2. Plan your budget wisely: On top of the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Oldsmar.
  3. Decide how long to go for: Now that you're up to speed on Oldsmar, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick an Oldsmar holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.