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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was CA $1,019, price is now CA $718 per person
CA $718
per person
Sep 22 - Sep 27
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8/10 Very good! (142 reviews)

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,387, price is now CA $861 per person
CA $861
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
9.6/10 Exceptional! (1,273 reviews)

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $1,392, price is now CA $949 per person
CA $949
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,096 reviews)
Beautiful comfortable rooms. Coffee in the morning and refreshments and sunsets on the balcony in the evening make for special moments. Short walk to the beach. Hoping to go back some day.

Reviewed on Aug 1, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $1,574, price is now CA $1,092 per person
CA $1,092
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
9.8/10 Exceptional! (16 reviews)
The property was very clean and all of the staff were so nice. We really enjoyed our stay.

Reviewed on Aug 1, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was CA $1,763, price is now CA $1,234 per person
CA $1,234
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
9.4/10 Exceptional! (3,564 reviews)

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Oldsmar Hotel Deals

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
3990 Tampa Rd Oldsmar FL
Fully refundable
The price is CA $122 per night from Aug 31 to Sep 1
CA $122
CA $138 total
Aug 31 - Sep 1
includes taxes & fees
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
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 $351 per night from Aug 9 to Aug 10
CA $351
CA $452 total
Aug 9 - Aug 10
includes taxes & fees
Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Aug 31 to Sep 1
CA $201
CA $228 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,475 reviews)
"Convenient location; friendly staff; clean but: too close to the highway and the small beach front can drawn in sewer smell. Not the quietest rooms, we stayed at the 15th floor and between elevators noise and highway; we had multiple sleepless nights. Parking is $28 a day and concierge is $34. Something ..."

Reviewed on Aug 1, 2026

The Westin Tampa Bay
See all 16,379 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 clear-water beaches or attend a sporting event in this family-friendly area.
See properties

What to do in Oldsmar

Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

CA $39
per adult
92% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
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
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $52
per adult
94% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
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 $718 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.