Oldsmar Vacations from $530

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $925, price is now $530 per person
$530
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Room was nice and comfortable. Had to wait for check in for a while but it understandable for peak time.

Reviewed on Feb 4, 2026

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $1,083, price is now $645 per person
$645
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The rooms were newly renovated and the staff were very helpful. Very roomy

Reviewed on Jan 23, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,665, price is now $1,013 per person
$1,013
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Great overall. The housekeeping is always behind but you just have to call multiple times.

Reviewed on Feb 4, 2026

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,036, price is now $635 per person
$635
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,193 reviews)
Great place to stay! Friendly staff. Spacious suites. Pet friendly. Heated pool.

Reviewed on Jan 31, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,393, price is now $854 per person
$854
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Hotel was great however they charged me full room rate when I was supposed to have it mostly paid for by one key cash credit…How do I resolve this?

Reviewed on Feb 4, 2026

Don't see what you're looking for?
See all available trips from Columbus to Oldsmar
View all trips

Discover the most popular places to visit in Oldsmar

Aerial photo Port of Tampa Florida

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
Tampa_SeminoleHardRockCasino_553248621563123174_05

Seminole Hard Rock Casino Tampa

Why not try your luck with a visit to Seminole Hard Rock Casino Tampa where you can enjoy the entertainment at this popular casino in Orient Park? Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

Seminole Hard Rock Casino Tampa

What to do in Oldsmar

Dolphins in downtown Tampa

1.5-hour Dolphin Sightseeing Cruise from Tampa

$31
per adult
78% of travellers recommend
1.5-hour Dolphin Sightseeing Cruise from Tampa
ZooTampa at Lowry Park Admission Ticket

ZooTampa at Lowry Park Admission Ticket

$52
per adult
98% of travellers recommend
ZooTampa at Lowry Park Admission Ticket
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
See all activities in Oldsmar

Oldsmar Hotel Deals

Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
$70 nightly
The price is $79 total per night from Mar 8 to Mar 9
$79 total
Mar 8 - Mar 9
Total with taxes and fees
6.2/10 (3,904 reviews)
Great breakfast, deposits were different amounts for 2 different stays which was odd but hotel was fine for 1 night

Reviewed on Feb 2, 2026

Ramada by Wyndham Tampa Westshore Airport South
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
$220 nightly
The price is $250 total per night from Feb 8 to Feb 9
$250 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (1,115 reviews)
Bed is always amazing

Reviewed on Feb 3, 2026

The Westin Tampa Bay
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
200 N Ashley Dr Tampa FL
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $212 total per night from Mar 8 to Mar 9
$212 total
Mar 8 - Mar 9
Total with taxes and fees
7/10 Good! (1,832 reviews)
Very nice staff who worked to make sure I had a great experience! They made the experience. The location was also beautiful and super convenient. The room itself did its job—there were some stains on the shower and some dirt but for the most part, it was clean and comfortable. Overall, a great ...

Reviewed on Jan 21, 2026

Hotel Tampa Riverwalk
See all 15,862 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oldsmar vacation package cost?
You can grab a vacation package to this top destination from $530 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.