Oldsmar Vacation Packages 2026 from $715

Oldsmar flight + hotel vacation packages

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

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$715

per person

Mar 11 - Mar 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This resort features a golf course, a full-service spa, and 3 restaurants. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,212

per person

Apr 10 - Apr 17

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.

Kompose Boutique Hotel

Save 100% on your flight

$835

per person

Apr 10 - Apr 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

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. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$868

per person

Apr 10 - Apr 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

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

Hilton Garden Inn Sarasota - Bradenton Airport

Save 100% on your flight

$1,043

per person

Apr 10 - Apr 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

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

Top Oldsmar hotels deals

Ramada by Wyndham Tampa Westshore Airport South

1200 N Westshore Blvd Tampa FL

$72 nightly

$82 total

Mar 8 - Mar 9

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4860 West Kennedy Boulevard Tampa FL

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$260 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-in, express check-out, and free airport shuttle. Free self parking, a coffee shop, and limo/town car service are also offered.

Free airport shuttle

Parking included

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$241 nightly

$272 total

Feb 10 - Feb 11

Total with taxes and fees

This resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor pools and perks like free WiFi.

On private beach

Pool

Quality Inn Airport - Cruise Port

1020 S Dale Mabry Hwy Tampa FL

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$127 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

$317 nightly

$358 total

Feb 10 - Feb 11

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 & Spa

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$334 nightly

$377 total

Feb 9 - Feb 10

Total with taxes and fees

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

Pool

Hot Tub

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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.

Popular places to visit

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.

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.

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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.

Frequently asked questions

How much are vacation packages to Oldsmar?

Your vacation daydreams can all come true in Oldsmar for as low as $715. 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.