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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.
ChartHouse Clearwater Beach Marina Hotel
The Avalon Club
CW Resort
Saddlebrook Resort
The Knickerbocker by Delphius
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Stay near popular Oldsmar attractions

What to do in Oldsmar

Oldsmar Hotel Deals

Courtyard by Marriott Tampa Oldsmar

Courtyard by Marriott Tampa Oldsmar

3 out of 5
4014 Tampa Rd Oldsmar FL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from Nov 29 to Nov 30
$106 total
Nov 29 - Nov 30
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"There were some kind of worm looking bugs in the room and the staff couldn't move us"

Reviewed on Nov 5, 2026

Courtyard by Marriott Tampa Oldsmar
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
$193 nightly
The price is $218 total per night from Nov 9 to Nov 10
$218 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (4,041 reviews)
"Room, food, and entire stay was amazing"

Reviewed on Nov 4, 2026

Wyndham Grand Clearwater Beach
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

4 out of 5
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $293 total per night from Nov 11 to Nov 12
$293 total
Nov 11 - Nov 12
Total with taxes and fees
Hyatt Regency Clearwater Beach Resort and Suites
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

What types of vacation packages are available in Oldsmar?
Oldsmar, known for its family-friendly attractions and outdoor activities, offers vacation packages tailored to different travel styles:
  • Family-friendly: A package with a stay at Courtyard by Marriott Tampa Oldsmar, rated 8.3 out of 10 by travelers, provides family rooms and an outdoor pool, making it an easy choice for those traveling with children.
  • Budget: For value-conscious travelers, Hilton Garden Inn Tampa Northwest/Oldsmar, also rated 8.3 out of 10 by travelers, offers free breakfast and an outdoor pool, with travelers frequently praising its great value.
  • Pet-friendly: If you're bringing your furry companion, Hilton Garden Inn Tampa Northwest/Oldsmar is a pet-friendly option, rated 8.3 out of 10 by travelers, providing a comfortable stay for everyone.
  • Packages with free breakfast: Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar, rated 9.3 out of 10 by travelers, is a strong choice for those prioritizing free breakfast to start their day.
How can I save money on a Oldsmar vacation package?
When you bundle, you can save up to 30%*. To save money on a Oldsmar package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
How much does an Oldsmar vacation package cost?
An Oldsmar vacation package typically costs around $800 per adult for a week-long trip. Lower-priced options start around $450 per adult, while premium packages can reach up to $1,250.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Oldsmar vacation package deals?
The cheapest Oldsmar vacation package deals can be as low as around $380 per adult for weekend trips. Separately, October and September typically have the lowest average monthly prices, around $670 to $680 per adult, typically for a 3-day trip. Bundling flights and hotel together also typically saves money on an Oldsmar vacation package — nearly all bookings save versus booking separately, with weekend trips typically saving around $45 per adult and week-long trips around $85 per adult. Longer, two-week trips can save even more, often around $100 per adult. Browse cheap vacation packages in Oldsmar on Expedia for current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Oldsmar?
The best time to go for an Oldsmar vacation package is typically from February through April, when the weather is pleasant and demand is highest. These months see the most visitors, so booking your Oldsmar vacation in advance is recommended.

For a more affordable trip, consider traveling in September, October, or January. These months tend to have lower package prices and fewer crowds, offering a quieter experience, though May, November, and August are also among the quieter times to visit.
What's included in an Oldsmar vacation package?
An Oldsmar vacation package lets you combine round-trip flights, a hotel stay, and a rental car, providing a convenient base for exploring this outdoor and nature destination. Most hotels offer free breakfast, giving you a relaxed start to each day. Many hotels also provide airport shuttle service to and from Tampa International Airport (TPA).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Oldsmar?
Families looking for the best vacation packages in Oldsmar can build a trip around a stay at Courtyard by Marriott Tampa Oldsmar, rated 8.3 out of 10 by travelers. This hotel offers family rooms, an outdoor pool, and a restaurant, making it an easy and convenient base for your vacation.

For couples seeking a relaxed getaway, a package featuring Hampton Inn & Suites Tampa Northwest/Oldsmar is a strong choice. Rated 8.6 out of 10 by travelers, it includes a hot tub and outdoor pool, with travelers often praising the friendly and helpful staff.

Travelers seeking value will find an Oldsmar vacation package with a stay at Hilton Garden Inn Tampa Northwest/Oldsmar appealing. This hotel, rated 8.3 out of 10 by travelers, includes free breakfast, an outdoor pool, and a restaurant, and is frequently highlighted by guests for its great value.

*Package availability and prices may change depending on dates and demand.
Is Oldsmar better suited for a beach vacation or a cultural trip?
Oldsmar is primarily an outdoor and nature destination, offering a mix of natural scenery and local history for your Oldsmar vacation. It provides convenient access to renowned Gulf Coast beaches like Clearwater Beach, about 18 miles away, and Siesta Key Beach, about 17 miles from central Oldsmar, making beach excursions a popular option.

For those interested in culture and history, Oldsmar was founded as a planned community in 1916 by Ransom E. Olds, and its heritage can be explored through local landmarks and annual events like Oldsmar Days and Nights. The nearby Tarpon Springs Sponge Docks, about 11 miles away, also offer a unique cultural experience. This blend allows travelers to customize their Oldsmar vacation to include both outdoor relaxation and historical exploration.
Is Oldsmar a good choice for a family vacation package?
Oldsmar is a strong choice for family vacation packages, known for its family-friendly attractions and outdoor activities. The destination's character aligns well with family travel, offering a relaxed atmosphere and diverse things to do.

For accommodations, Courtyard by Marriott Tampa Oldsmar is a family-friendly option rated 8.3 out of 10 by travelers, offering family rooms, an outdoor pool, and a restaurant, making it a comfortable base for your stay.

Families can enjoy a variety of activities. Lake Tarpon, about 7 miles from central Oldsmar, provides opportunities for boating, fishing, and enjoying nature together. Your Oldsmar vacation package can be customized around these family-friendly experiences.
What is the best time to book an Oldsmar vacation package?
Book your Oldsmar vacation package around 3 weeks before you travel. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 1 and 6 weeks out.

From June to August are the most popular months for Oldsmar packages, so booking earlier is advisable if you're traveling during these months.
What are the top things to do in Oldsmar?
An Oldsmar vacation offers a variety of activities, from local attractions to nearby natural and coastal spots:

Browse and book things to do in Oldsmar on Expedia.
How many days do you need for an Oldsmar vacation?
Most Oldsmar vacation packages last around 4 days, which provide ample time to explore local attractions and enjoy nearby natural spots. Within this timeframe, you could visit Tampa Bay Downs and the Oldsmar Flea Market, explore Lake Tarpon, and take a day trip to the Tarpon Springs Sponge Docks.

Many travelers opt for weekend trips to Oldsmar, while about half choose week-long stays to allow for more relaxed exploration or additional excursions to places like Clearwater Beach. A longer Oldsmar vacation package could also include visits to other Gulf Coast attractions.
Is Oldsmar a good destination for a weekend vacation?
Oldsmar is a good destination for a weekend vacation package, with about half of package bookings being for 1 to 3 days. A short trip allows you to experience local highlights such as browsing the Oldsmar Flea Market and enjoying outdoor activities on Lake Tarpon.

While many travelers choose to extend their Oldsmar vacation for a week to explore more of the surrounding area and Gulf Coast beaches, a weekend getaway still offers a fulfilling experience focused on the town's unique attractions and natural surroundings.
Do you need to rent a car in Oldsmar, or is public transport enough?
For Oldsmar vacation packages with flights, renting a car is generally recommended for maximum flexibility, especially since Oldsmar is an outdoor and nature destination outside a major city. While some hotels are within walking distance of central Oldsmar, many popular attractions and natural sites are spread out.

A rental car makes it easy to reach places like Weeki Wachee Springs, about 12 miles away, or the Tarpon Springs Sponge Docks, about 11 miles from central Oldsmar. It also provides convenient access to Gulf Coast beaches such as Clearwater Beach, about 18 miles away, which is ideal for those planning Oldsmar beach vacation packages. For arrivals, Tampa International Airport (TPA) and St. Petersburg-Clearwater International Airport (PIE) serve the area, and a car allows for easy transfers and exploration beyond your hotel.
Are Oldsmar vacation package hotels conveniently located?
Oldsmar vacation package hotels are generally conveniently located, with many properties situated within easy reach of central Oldsmar. For instance, Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG, Hampton Inn & Suites Tampa Northwest/Oldsmar, and Hilton Garden Inn Tampa Northwest/Oldsmar are all about a 10-minute walk from the heart of Oldsmar.

These central locations provide good access to local dining and attractions. For travelers seeking different surroundings, areas like East Lake Woodlands offer hotels closer to Tampa Bay and Innisbrook Golf Club, while Quail Forest provides options near natural spots like Keystone Lake.
Can I change or cancel my Oldsmar vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Oldsmar vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Oldsmar vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Oldsmar vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Oldsmar?
To find last-minute vacation packages to Oldsmar, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Oldsmar vacation packages?
Free cancellation on a Oldsmar vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Oldsmar vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Oldsmar getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Oldsmar vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.