Oldsmar Vacations from $565

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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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $835, price is now $565 per person
$565
per person
Jun 23 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (78 reviews)
This is an old school Florida motel. It is clean and quaint. It's not the Hilton, but that's the draw. Convenient location.

Reviewed on Apr 20, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $840, price is now $566 per person
$566
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,196 reviews)
Loved the location and the roof top pool and bar!!

Reviewed on May 6, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was $2,379, price is now $1,647 per person
$1,647
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
It was actually perfect. Amazing beach, amazing spacious room. One of our new top picks for vacay spots.

Reviewed on Apr 30, 2026

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $1,176, price is now $817 per person
$817
per person
Jul 22 - Jul 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (662 reviews)
We enjoyed our stay here and highly recommend it to anyone traveling to the area. The staff was super helpful. Parking does get overcrowded due to the pickleball courts and volleyball courts but we always had a place to park. The Skybar is a good place to enjoy a cold beverage and take in the view!

Reviewed on May 7, 2026

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort

3 out of 5
Save 100% on your flight
Price was $1,872, price is now $1,305 per person
$1,305
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (865 reviews)
Although we did not choose to stay at our hotel because there was little to do around the hotel for 4 teenage boys the customer service was wonderful. Val was amazing and understanding! It is a wonderful option if you have a family with littler children, want to cook your own meals and enjoy thr pool set back from a breathe taking beach! Place was spacious !

Reviewed on Apr 28, 2026

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Discover the most popular places to visit in Oldsmar

Aerial panoramic view of industrial area and port of Tampa, Florida.

Port of Tampa

4/5(1,798 reviews)

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

Busch Gardens Tampa Bay

4.5/5(1,691 reviews)

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
Tampa_RaymondJamesStadium_503050_03

Raymond James Stadium

4.5/5(740 reviews)

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

Sharks in 500,000 gallon Coral Reef habitat

The Florida Aquarium in Tampa General Admission

$40
per adult
86% of travellers recommend
The Florida Aquarium in Tampa General Admission
1.5-hour Dolphin Sightseeing Cruise from Tampa

1.5-hour Dolphin Sightseeing Cruise from Tampa

$31
per adult
80% of travellers recommend
1.5-hour Dolphin Sightseeing Cruise from Tampa
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$37
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
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
$107 nightly
The price is $121 total per night from May 11 to May 12
$121 total
May 11 - May 12
Total with taxes and fees
9.4/10 Exceptional! (1,107 reviews)
Room and bathroom were very clean, tv and a/c worked well. Breakfast was a good variety of hot and cold items. Good coffee.

Reviewed on May 5, 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
$337 nightly
The price is $380 total per night from May 31 to Jun 1
$380 total
May 31 - Jun 1
Total with taxes and fees
9.4/10 Exceptional! (3,218 reviews)
Definitely returning. Amazing hospitality from the moment you drive up. Food choices could be better at the poolside bar, while food at ocean hai was very yummy, just expensive. all very worth it. Walking distance to pier 60 and many boat tours. Private beach chairs are such a nice perk with reasonable, ...

Reviewed on May 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
$211 nightly
The price is $239 total per night from Jun 7 to Jun 8
$239 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (2,606 reviews)
All

Reviewed on May 7, 2026

Hilton Clearwater Beach Resort & Spa
See all 16,266 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 $565 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.