Oldsmar Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, 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.

Top Oldsmar Vacation Deals

Price found within the past 48 hours. Click for updated prices.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
The property was quiet, clean and comfortable. The customer service was professional and above average. I would not hesitate to book again. Two bedrooms and two bathrooms, living room and full kitchen was plenty room for husband and I. Only stayed one night but wished it was longer.

Reviewed on Jun. 26, 2025

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
6.2/10 (1,003 reviews)
Wish the big pool was open

Reviewed on Jul. 11, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
Great location with convenient stores, restaurants,very clean the hotel with excellent guest service. Overall everything was great at our stay.

Reviewed on Jul. 13, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view.

Reviewed on Jul. 10, 2025

Clearwater Beach Hotel Suites

Clearwater Beach Hotel Suites

2.5 out of 5
Save 100% on your flight
per person
Oct 5 - Oct 12
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews

Ready to book your vacation to Oldsmar?

 

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Oldsmar Hotel Deals

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 CA $255 per night from Aug 7 to Aug 8
CA $255
CA $342 total
Aug 7 - Aug 8
includes taxes & fees
8/10 Very Good! (2,001 reviews)
"Great servics great location"

Reviewed on Jul. 12, 2025

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 3 to Aug 4
CA $207
CA $235 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,651 reviews)
"Nice overnight stay! Super comfortable"

Reviewed on Jul. 12, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
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 CA $349 per night from Aug 3 to Aug 4
CA $349
CA $449 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (2,363 reviews)
An excellent hotel with amazing staff.
"Our stay was excellent. Tammy (check in) was most amazing and helpful. We will only stay here when visiting Clearwater. Thanks!"

Reviewed on Jul. 11, 2025

Wyndham Grand Clearwater Beach
See all 14,999 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Oldsmar

Busch Gardens Tampa Bay

Busch Gardens Tampa Bay

4.5/5(77 reviews)

Exotic animals and thrill rides all on the one site at this theme park and zoo designed for the whole family.

Busch Gardens Tampa Bay
Raymond James Stadium

Raymond James Stadium

4.5/5(29 reviews)

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

Raymond James Stadium
Tampa Riverwalk

Tampa Riverwalk

4.5/5(92 reviews)

Walk, bike or rollerblade along Tampa’s waterside neighborhood, with public art, museums, restaurants and more attractions right on the waterfront.

Tampa Riverwalk

What to do in Oldsmar

Sharks in 500,000 gallon Coral Reef habitat

The Florida Aquarium in Tampa General Admission

CA $46
per adult
84% of travellers recommend
The Florida Aquarium in Tampa General Admission
Self-Guided Driving Bundle of Florida Tours

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

CA $55
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

CA $33
per adult
100% of travellers recommend
Tampa Terrors Ghost Tour By US Ghost Adventures
See all activities in Oldsmar

Frequently asked questions

How much does an Oldsmar vacation package cost?
You can snap up a vacation package to this top destination from CA $475 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.