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.
The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was CA $1,249, price is now CA $740 per person
CA $740
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.8/10 Excellent! (434 reviews)

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $1,518, price is now CA $828 per person
CA $828
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
.

Reviewed on Oct 31, 2026

CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was CA $1,474, price is now CA $873 per person
CA $873
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was CA $1,663, price is now CA $998 per person
CA $998
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (615 reviews)

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was CA $1,311, price is now CA $806 per person
CA $806
per person
Jan 3 - Jan 8
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (1,532 reviews)
My stay.was Oct 26-29...I had a very comfortable and relaxing stay. My hotel amd room was beautiful. The only thing I didn't care for was the loud band. That wasnt from the hotel. It was across the street from hotel. I would stay here again.

Reviewed on Oct 31, 2026

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Oldsmar Hotel Deals

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 CA $137 per night from Nov 29 to Nov 30
CA $137
CA $155 total
Nov 29 - Nov 30
includes taxes & fees
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 CA $331 per night from Nov 5 to Nov 6
CA $331
CA $429 total
Nov 5 - Nov 6
includes taxes & fees
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 CA $313 per night from Nov 11 to Nov 12
CA $313
CA $409 total
Nov 11 - Nov 12
includes taxes & fees
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

What to do in Oldsmar

Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

CA $52
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

CA $40
per adult
96% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
Tarpon Springs: Evening Dolphin Cruise

Tarpon Springs: Evening Dolphin Cruise

CA $41
per adult
90% of travellers recommend
Tarpon Springs: Evening Dolphin Cruise
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 $740 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.

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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.