
Oldsmar Vacations from $670
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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.
The Latest Oldsmar vacation packages
Price found within the past 48 hours. Click for updated prices.

Hibiscus Suites - Gateway to Siesta Key
Price was $1,026, price is now $670 per person
$670
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,471 reviews)
Clean rooms, great staff, air condition, jumping, great parking available
Reviewed on Nov 10, 2026


Crystal Palms Beach Resort
Sunshine Beach
Price was $1,169, price is now $721 per person
$721
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,409 reviews)
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating
Reviewed on Nov 7, 2026


The Roth Hotel
Sunset Beach
Price was $1,349, price is now $855 per person
$855
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
10/10 Exceptional! (119 reviews)
Truly a treasure!!! Don’t miss the opportunity to stay here. Love the proximity to the beach. The dock was so tranquil and great for sipping coffee in the mornings and my son loved to fish and watch for dolphins & manatees!
Reviewed on Sep 12, 2026
Stay near popular Oldsmar attractions
What to do in Oldsmar

Starlite Infinity Evening Yacht Cruise Clearwater
$37
per adult
90% of travellers recommend

Clearwater Beach: Dolphin & Island Sandbar Cruise
$28
per adult
96% of travellers recommend

1.5-hour Dolphin Sightseeing Cruise from Tampa
$31
per adult
80% of travellers recommend
Oldsmar Hotel Deals

Courtyard by Marriott Tampa Oldsmar
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Nov 22 to Nov 23
$105 total
Nov 22 - Nov 23
Total with taxes and fees
8.8/10 Excellent! (1,011 reviews)
"Great"
Reviewed on Nov 11, 2026

Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$240 nightly
The price is $271 total per night from Dec 13 to Dec 14
$271 total
Dec 13 - Dec 14
Total with taxes and fees
9.4/10 Exceptional! (4,052 reviews)
"An absolutely wonderful experience! ⭐⭐⭐⭐⭐ My family and I spent the weekend at this amazing beachfront hotel, and it exceeded all our expectations! Stunning ocean views, an unbeatable location, spotless accommodations, exceptional service, and fantastic restaurants. Everything you need for a perfect ..."
Reviewed on Nov 10, 2026

Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$267 nightly
The price is $301 total per night from Dec 8 to Dec 9
$301 total
Dec 8 - Dec 9
Total with taxes and fees
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.
Find the Best Oldsmar Vacation Packages
Oldsmar Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tampa Intl. Airport (TPA) |
Population | 14,200 |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | ZooTampa at Lowry Park, Ben T. Davis Beach and Big Cat Rescue |
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