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.
Clearwater Suites

Clearwater Suites

2.5 out of 5
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.8/10 Excellent! (12 reviews)
Nice very spacious room. Close tobthe beach and restaurants.

Reviewed on Aug. 11, 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (438 reviews)
Nice place...near the beach, would've rated it a 5 but I was denied a later checkout. Other than that a very nice place convenient to all the sites.

Reviewed on Aug. 8, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
Well run property, great gulf views and friendly staff.

Reviewed on Aug. 12, 2025

Inn on the Beach

Inn on the Beach

2.5 out of 5
Pass-a-Grille
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.8/10 Exceptional! (329 reviews)
Well designed, well thought out room with almost everything we needed. Appreciated the beach chairs, umbrellas & towels. Frig was great but a small microwave would have been a big plus. Ceiling fan was noisy & we asked for our floor to be swept & mopped, which didn’t happen. We had to brush our feet off before getting in bed. Great linens, towels & robed as well as quality toiletries. If we stay again we’ll ask for second floor as there was a lot of noise, chairs scraping, furniture moving & loud walking at all times of day & night, directly above us. Great location! Loved the area.

Reviewed on Jul. 30, 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
per person
Oct 3 - Oct 6
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.2/10 Very Good! (1,345 reviews)
Needs some upgrades on current rooms, but we had a great stay there

Reviewed on Aug. 11, 2025

Ready to book your vacation to Oldsmar?

 

Choose your dates

Oldsmar Hotel Deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
The price is CA $215 per night from Aug 29 to Aug 30
CA $215
CA $245 total
Aug 29 - Aug 30
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Very good experience I love it there"

Reviewed on Aug. 11, 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 CA $234 per night from Aug 17 to Aug 18
CA $234
CA $313 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Excellent!!!"

Reviewed on Aug. 12, 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 CA $221 per night from Aug 18 to Aug 19
CA $221
CA $305 total
Aug 18 - Aug 19
includes taxes & fees
8/10 Very Good! (2,108 reviews)
"Great location right on the beach! Pool aside Bar is Excellent!"

Reviewed on Aug. 10, 2025

Hilton Clearwater Beach Resort & Spa
See all 15,132 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
82% 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 $36
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 $403 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.