Oldsmar Vacation Packages 2026 from $434

Oldsmar flight + hotel vacation packages

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

Mar Bay Motel &Suites

Save 100% on your flight

$434

per person

May 13 - May 17

found 1 day ago

Roundtrip non-stop 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.

Voyager Beach Club

Sunshine Beach

$585

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This condo features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a library, and a picnic area are also on offer.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$592

per person

Jun 14 - Jun 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$610

per person

Jun 14 - Jun 19

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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,261

per person

May 6 - May 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Top Oldsmar hotels deals

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

3990 Tampa Rd Oldsmar FL

Free Cancellation

$129 total

per night

May 6 - May 7

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

$363 total

per night

May 7 - May 8

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

Hotel Tampa Riverwalk

200 N Ashley Dr Tampa FL

Free Cancellation

Reserve now, pay when you stay

$155 total

per night

May 3 - May 4

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the outdoor pool and conveniences like a 24-hour front desk and wedding services.

Pool

Pet friendly

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$315 total

per night

May 7 - May 8

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

Ramada by Wyndham Tampa Westshore Airport South

1200 N Westshore Blvd Tampa FL

$129 total

per night

Apr 7 - Apr 8

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

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Free Cancellation

Reserve now, pay when you stay

$529 total

per night

Apr 13 - Apr 14

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

Don't see what you're looking for?

See all available properties in Oldsmar

View all properties

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

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.

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.

Tampa Riverwalk

After visiting Tampa Riverwalk, make a plan to see the other sights and activities in Tampa. Experience the great live music 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 $434. 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.