Oldsmar Packages (Flight + Hotel)

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Top hotels in Oldsmar

Courtyard by Marriott Tampa Oldsmar

Courtyard by Marriott Tampa Oldsmar

3 out of 5
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
The price is ฿3,314 per night from 29 Nov to 30 Nov
฿3,314
฿3,744 total
29 Nov - 30 Nov
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Great place to stay on work trip"

Reviewed on 1 Nov 2026

Courtyard by Marriott Tampa Oldsmar
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is ฿8,001 per night from 5 Nov to 6 Nov
฿8,001
฿10,377 total
5 Nov - 6 Nov
includes taxes & fees
9.4/10 Exceptional! (4,033 reviews)
"Great location, the Beach is across the street. Very friendly staff."

Reviewed on 2 Nov 2026

Wyndham Grand Clearwater Beach
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

4 out of 5
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is ฿7,575 per night from 11 Nov to 12 Nov
฿7,575
฿9,895 total
11 Nov - 12 Nov
includes taxes & fees
9.4/10 Exceptional! (2,485 reviews)
"Outstanding place and great staff"

Reviewed on 1 Nov 2026

Hyatt Regency Clearwater Beach Resort and Suites
See all 16,577 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.

Stay near popular Oldsmar attractions

Oldsmar Flea Market

8.2/10 (64 reviews)
This sprawling 28-acre marketplace showcases hundreds of vendors selling everything from antiques to fresh produce. Arrive early to browse the treasures with fewer crowds and bring cash for unique finds.
See properties

What to do in Oldsmar

Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

฿935
per adult
94% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

฿1,225
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

฿1,050
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.