Oldsmar Vacation Packages 2026 from $791

Oldsmar flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Fold Hotels Indian Shores

Save 100% on your flight

$791

per person

Nov 26 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, a terrace, and laundry facilities are also on offer.

Cedar Cove Resort and Cottages

$1,287

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,494

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,038

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Legacy Hotel at IMG Academy

Save 100% on your flight

$1,509

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Top Oldsmar hotels deals

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

3990 Tampa Rd Oldsmar FL

Free Cancellation

$97 nightly

$110 total

Sep 30 - Oct 1

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.

Pool

Breakfast included

Courtyard by Marriott Tampa Oldsmar

4014 Tampa Rd Oldsmar FL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$101 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$283 nightly

$319 total

Sep 20 - Sep 21

Total with taxes and fees

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Pool

Hot Tub

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$247 nightly

$279 total

Sep 18 - Sep 19

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this resort. Families will appreciate the children's pool and onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Hot Tub

Hilton Tampa Airport Westshore

2225 N Lois Ave Tampa FL

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$114 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, express check-in, and free airport shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Pool

Free airport shuttle

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3001 University Center Dr Tampa FL

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$114 total

Oct 6 - Oct 7

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Free perks include buffet breakfast, free self parking, and a theme park shuttle. Free WiFi in public areas, a garden, and luggage storage are also on offer.

Pool

Breakfast included

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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.

Stay near popular Oldsmar attractions

Oldsmar Flea Market

8.2/10 (64 reviews)

You can find the perfect gifts to bring home at Oldsmar Flea Market during your stay in Oldsmar. Stroll along the beautiful beaches or attend a sporting event in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Oldsmar?

Your vacation daydreams can all come true in Oldsmar for as low as $791. Vacation packages include flights and hotels, so organizing everything should be a piece of cake. The only thing you'll have to focus on is having a good time.

How long should my Oldsmar vacation be?

Your Oldsmar getaway can be as long as you'd like it to be, but most people stay roughly 3 nights. Like to get out and uncover some hidden treasures? Book a couple more nights and experience another side of this place.

Where can I get the best vacation package deals for Oldsmar?

Travelocity has all you need to score a sensational Oldsmar package deal. Take your pick of 400 airlines and 1,000,000 properties across the globe and put together a vacation package that's suited to you. With so many options at hand, it's easy to organize your next big adventure.

Why should I book my Oldsmar vacation bundle with Travelocity?

Because life is all about the journey, and we have everything you need to help you on the way. With our top-quality service and Price Match Guarantee, you can organize your trip with confidence. What's more, you can sleep easy while you're away knowing we're here for you with our 24/7 customer support.

Can I save on my Oldsmar car rental if I combine it with hotels and flights?

You most certainly can — bundle your flight, hotel and car into an Oldsmar vacation package and you can save a ton. With so much to discover in Oldsmar, having your own ride will make exploring a joy. Once you've slid into the driver's seat, put the stereo on and head to Universal Studios Florida, a famous attraction roughly 80 mi from Oldsmar.

Which airport is best for Oldsmar?

Tampa Intl. Airport (TPA) is 9 mi from the city center and is the beginning point for many memorable experiences. Alternatively, Sarasota-Bradenton Intl. Airport (SRQ) is 45 mi away from central Oldsmar and St. Petersburg-Clearwater Intl. Airport (PIE) is 9 mi away from central Oldsmar.

What is there to do in Oldsmar?

While taking the path less traveled can be rewarding, you shouldn't miss the popular sights that make a destination famous. Oldsmar Flea Market and Oldsmar Historical Society Museum are just two of them in Oldsmar.

Where should I stay when visiting Oldsmar?

The Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar, an IHG Hotel is popular with many visitors. Book now to avoid missing out.