Oldsmar Vacation Packages 2026 from $503

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

$503

per person

Mar 5 - Mar 10

found 1 day ago

Roundtrip non-stop 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.

Delray House With Hot tub & Game Room

Palm River-Clair Mel

Save 100% on your flight

$545

per person

Feb 21 - Feb 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, free self parking, and a virtual front desk are featured at this vacation home. Dry cleaning is also provided.

Family Home Tampa

Forest Hills

Save 100% on your flight

$689

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This guesthouse includes a garden and a virtual front desk. Take advantage of the free self parking.

Mar Bay Motel &Suites

Save 100% on your flight

$558

per person

Mar 11 - Mar 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,972

per person

Mar 14 - Mar 21

found 11 hours ago

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.

Top Oldsmar hotels deals

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

3990 Tampa Rd Oldsmar FL

Free Cancellation

$137 nightly

$155 total

Jan 11 - Jan 12, 2026

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

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$241 nightly

$272 total

Jan 4 - Jan 5, 2026

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

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$190 nightly

$215 total

Jan 11 - Jan 12, 2026

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

Hotel Alba, Tapestry Collection by Hilton

5303 W Kennedy Blvd Tampa FL

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$215 total

Jan 2 - Jan 3, 2026

Total with taxes and fees

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. There's an outdoor pool on site, and concierge services and wedding services are also offered.

Pool

Free airport shuttle

Ramada by Wyndham Tampa Westshore Airport South

1200 N Westshore Blvd Tampa FL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

Jan 4 - Jan 5, 2026

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

Hotel South Tampa & Suites

3314 S Dale Mabry Hwy Tampa FL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$106 total

Jan 4 - Jan 5, 2026

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. Guests will appreciate freebies like continental breakfast and free self parking.

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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

4/5(1,773 reviews)

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

4.5/5(1,674 reviews)

Exotic animals and thrill rides all on the one site at this theme park and zoo designed for the whole family.

Tampa Riverwalk

4.5/5(1,586 reviews)

With a visit to Tampa Riverwalk, a popular shopping spot in Tampa, you can find the perfect gifts to bring home. Experience the acclaimed theater scene or attend a hockey game in this walkable area.

Frequently asked questions

How much are vacation packages to Oldsmar?

Your vacation daydreams can all come true in Oldsmar for as low as $503. 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.