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.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,060, price is now CA $757 per person
CA $757
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
The front desk agent made our check in so easy. Hotel is very close to the beach and amenities were great. 10/10 can’t wait to be back!

Reviewed on Jul 7, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,858, price is now CA $1,778 per person
CA $1,778
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.2/10 Wonderful! (543 reviews)
Returned customer, great place to stay for four nights.

Reviewed on Jul 3, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,786, price is now CA $1,821 per person
CA $1,821
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
No reviews
I had a wonderful stay at CW-Hotel. From the moment I arrived, the staff were welcoming, professional, and genuinely helpful. All the rooms are gorgeous and massive suites. They have kitchen and full bathrooms with full washer and dryer. The hotel’s location is right near the beach with easy access to nearby attractions, restaurants, and transportation. I also appreciated the attention to detail throughout the property, which made the experience feel both comfortable and enjoyable. What stood out most was the excellent customer service. The team went above and beyond to ensure my stay was pleasant, and their hospitality made a lasting impression. I would gladly stay at CW-Hotel again and highly recommend it to anyone looking for a clean, comfortable, and well-managed hotel with outstanding service.

Reviewed on Jul 7, 2026

The Hotel Zamora

The Hotel Zamora

4 out of 5
Price was CA $1,857, price is now CA $1,319 per person
CA $1,319
per person
Aug 23 - Aug 30
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (354 reviews)
Excellent experience! Will definitely be staying here again in the future! Friendly kind staff, very clean hotel

Reviewed on Jul 5, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,495, price is now CA $2,589 per person
CA $2,589
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
6/10 (3 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 $152 per night from Jul 26 to Jul 27
CA $152
CA $172 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,265 reviews)
"excellent breakfast room clean and ready excellent service. 10/10 recommend"

Reviewed on Jul 6, 2026

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 $355 per night from Aug 2 to Aug 3
CA $355
CA $457 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (3,485 reviews)
"Lovely property beautiful views"

Reviewed on Jul 7, 2026

Wyndham Grand Clearwater Beach
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 $297 per night from Jul 15 to Jul 16
CA $297
CA $392 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very good! (2,782 reviews)
"…."

Reviewed on Jul 8, 2026

Hilton Clearwater Beach Resort & Spa
See all 16,247 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

Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

CA $40
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

CA $95
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $53
per adult
92% 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 $757 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.