Oldsmar Vacation Packages 2026 from $628

Oldsmar flight + hotel vacation packages

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$628

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) 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.

Cedar Cove Resort and Cottages

Save 100% on your flight

$779

per person

Dec 14 - Dec 19

found 10 hours ago

Roundtrip flight included

Minneapolis (MSP) 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.

Stylish Treasure Island Escape

Sunshine Beach

Save 100% on your flight

$4,987

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

This apartment featured laundry facilities and a virtual front desk. Take advantage of the free self parking.

4BR Spacious Paradise

Siesta Key Village

Save 100% on your flight

$1,014

per person

Dec 5 - Dec 12

found 9 hours ago

Roundtrip non-stop flight included

Providence (PVD) to Tampa (TPA)

An outdoor pool, free self parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A garden, a picnic area, and barbecue grills are also on offer.

Seaside at Anna Maria Island Inn

Save 100% on your flight

$1,475

per person

Dec 14 - Dec 19

found 10 hours ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.

Top Oldsmar hotels deals

Courtyard by Marriott Tampa Oldsmar

4014 Tampa Rd Oldsmar FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$105 total

Oct 7 - Oct 8

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

$250 nightly

$283 total

Oct 28 - Oct 29

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.

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$234 nightly

$264 total

Oct 5 - Oct 6

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

$110 nightly

$124 total

Oct 12 - Oct 13

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

Four Points by Sheraton Suites Tampa Airport Westshore

4400 W Cypress St Tampa FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$106 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities 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

$106 nightly

$120 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.

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Frequently asked questions

How much are vacation packages to Oldsmar?

Your vacation daydreams can all come true in Oldsmar for as low as $628. 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.