Oldsmar Vacations from $515

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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.
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
Price was $852, price is now $515 per person
$515
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
8.6/10 Excellent! (485 reviews)
The staff has been just awesome. From the moment we came in to check in! Cherish was so friendly and actually let us check in early and our room was ready. We have a gorgeous view overlooking the Bay. What else is fantastic is we have access to all the properties if we want to go to beachside! This place is a hidden gem!!!!

Reviewed on Oct 24, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $1,458, price is now $757 per person
$757
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (466 reviews)
Overall the property was clean; however, it was a great disappointment to see the street light with wires as an ocean view literally right outside your balcony. I also didn’t appreciate upon greeting the staff stressed about the fees instead of stressing what is already included, such as the beach chairs, umbrella etc…

Reviewed on Oct 15, 2025

Villa Valentino Luxury 8BR Villa & Pool

Villa Valentino Luxury 8BR Villa & Pool

3 out of 5
Allen's Ridge
Price was $6,167, price is now $3,613 per person
$3,613
per person
Jan 5 - Jan 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
No reviews
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $966, price is now $587 per person
$587
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
Great front desk staff ! Very kind and helpful

Reviewed on Oct 27, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,351, price is now $840 per person
$840
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (669 reviews)
Very clean, and quiet.

Reviewed on Oct 31, 2025

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Discover the most popular places to visit in Oldsmar

Port of Tampa

Port of Tampa

Explore the waterfront in Tampa with a trip to Port of Tampa. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Port of Tampa
Busch Gardens Tampa Bay showing rides

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.

Busch Gardens Tampa Bay
GO PACK GO

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.

Raymond James Stadium

What to do in Oldsmar

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
ZooTampa at Lowry Park Admission Ticket

ZooTampa at Lowry Park Admission Ticket

$52
per adult
94% of travellers recommend
ZooTampa at Lowry Park Admission Ticket
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
See all activities in Oldsmar

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
$113 nightly
The price is $128 total per night from Nov 5 to Nov 6
$128 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (1,045 reviews)
Everything about this property was excellent. From the staff at the front desk to the kitchen staff who took care of the breakfast and the ladies who cleaned the rooms, everything was great. Everyone we met was accommodating and always took care of anything we needed. We would definitely stay here ...

Reviewed on Oct 28, 2025

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

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
$135 nightly
The price is $153 total per night from Nov 23 to Nov 24
$153 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,031 reviews)
Just perfect

Reviewed on Oct 27, 2025

The Westin Tampa Bay
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
3314 S Dale Mabry Hwy, Tampa, FL
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Nov 18 to Nov 19
$85 total
Nov 18 - Nov 19
Total with taxes and fees
8.6/10 Excellent! (1,551 reviews)
Breakfast was great love the pool clean room and staff was great

Reviewed on Oct 27, 2025

Hotel South Tampa & Suites
See all 15,650 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.

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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Frequently asked questions

How much does an Oldsmar vacation package cost?
You can grab a vacation package to this top destination from $515 on Expedia. However, how much your vacation to Oldsmar costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Oldsmar?
If you're hoping to book a cheap Oldsmar vacation package, consider traveling in January, April and June. You'll typically find lower rates on flights and accommodations during these months — perfect for travelers wishing to save money.
How many days is enough for Oldsmar?
With a well-planned schedule, you can easily tick off the main Oldsmar attractions in a few days. But if you want to explore off the beaten track or go on day trips, consider booking your Oldsmar vacation for longer.
Is it worth booking a vacation package to Oldsmar?
Whether you're planning to explore attractions like Oldsmar Flea Market and Oldsmar Historical Society Museum, or eager to experience its top-notch nature and history, an Oldsmar vacation is sure to exceed your expectations. Book your getaway with Expedia and find out why Oldsmar is such a good vacation destination.
How to find the best Oldsmar package deals?
Start your search for an Oldsmar package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Oldsmar package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oldsmar getaway off to a flying start.
Is it cheaper to book an Oldsmar vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights separately. Better still, you can tailor your Oldsmar getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Oldsmar?
If you've got your Oldsmar travel dates locked in, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Oldsmar?

  1. Choose your dates: What you'd like to do in Oldsmar and your favorite season can help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Oldsmar.
  3. Use Expedia's trip planning tool to explore Oldsmar: Research every part of your trip to Oldsmar with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the sights and activities you want to get to in Oldsmar. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Oldsmar vacation package.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some fun things to do in Oldsmar. Book tickets or make reservations in advance to save time and avoid the stress of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Oldsmar vacation packages?
If you're anything like us, you love traveling but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Oldsmar vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.