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.
Pelican Pointe Clearwater Beach Hotel
Price was CA $1,374, price is now CA $978 per person
CA $978
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,008 reviews)
The was a 3 night stay for my wife and I. Room was very clean and nice. Its not fancy but was a great place to sleep ans shower while spending time at the beach. You can walk to beach and restaurant easily. I will be back for sure. Oh and all the staff were super nice.
Reviewed on May 29, 2026
Wyndham Grand Clearwater Beach
Price was CA $1,952, price is now CA $1,316 per person
CA $1,316
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (3,252 reviews)
Definitely add $100 to the cost of the room
Parking $40 Day
Resort fees $35 per day
Oceanfront views were fabulous
Room was fabulous
Best seafood is Frenchy’s
Marina Cantina was great also
Reviewed on May 29, 2026
ChartHouse Clearwater Beach Marina Hotel
Price was CA $1,671, price is now CA $1,188 per person
CA $1,188
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,034 reviews)
Perfect place to take the family. They don't offer breakfast but there's plenty of places to eat with in walking distance. Will be staying again.
Reviewed on May 29, 2026
Cedar Cove Resort and Cottages
Price was CA $1,851, price is now CA $1,343 per person
CA $1,343
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (515 reviews)
Everything was excellent; however did not disclose property was on the second floor and there was no elevator.
Reviewed on May 28, 2026
Oldsmar Hotel Deals
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
3990 Tampa Rd Oldsmar FL
Fully refundable
The price is CA $149 per night from Jun 7 to Jun 8
CA $149
CA $168 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (1,156 reviews)
"I wouldn't recommend staying there"
Reviewed on May 28, 2026
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $419 per night from Jun 24 to Jun 25
CA $419
CA $528 total
Jun 24 - Jun 25
includes taxes & fees
9.4/10 Exceptional! (3,294 reviews)
"Definitely add $100 to the cost of the room Parking $40 Day Resort fees $35 per day Oceanfront views were fabulous Room was fabulous Best seafood is Frenchy’s Marina Cantina was great also"
Reviewed on May 29, 2026
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is CA $240 per night from Jun 6 to Jun 7
CA $240
CA $272 total
Jun 6 - Jun 7
includes taxes & fees
8.6/10 Excellent! (1,334 reviews)
"Never was mentioned the pool was not finished..only upon arrival did we find out.. so two Full days after our cruise ..we had to uber to other places for pool activities.. Disappointed....."
Reviewed on May 30, 2026
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.
Discover the most popular places to visit in Oldsmar
Busch Gardens Tampa Bay
Exotic animals and thrill rides all on the one site at this theme park and zoo designed for the whole family.
Raymond James Stadium
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.
Tampa Riverwalk
Walk, bike or rollerblade along Tampa’s waterside neighborhood, with public art, museums, restaurants and more attractions right on the waterfront.
What to do in Oldsmar
Pirate Adventure Cruise - John's Pass
CA $61
per adult
100% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
CA $50
per adult
90% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
CA $91
per adult
100% of travellers recommend
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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.
