Hillsborough County Vacation Packages 2026 from $315

Search vacation packages deals in Hillsborough County's top destinations

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Hillsborough County flight + hotel vacation packages

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

Westgate Towers Resort

$315

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Residence Inn by Marriott Daytona Beach Oceanfront

$923

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

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 24-hour gym and free buffet breakfast each morning.

Westgate Vacation Villas Resort

Save 100% on your flight

$397

per person

Apr 4 - Apr 10

found 18 hours ago

Roundtrip flight included

Detroit (DTW) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

$806

per person

Apr 4 - Apr 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.

Westgate Cocoa Beach Resort

$1,007

per person

Feb 22 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Top Hillsborough County hotels deals

Ramada by Wyndham Tampa Westshore Airport South

1200 N Westshore Blvd Tampa FL

$82 nightly

$93 total

Feb 8 - Feb 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

Grand Hyatt Tampa Bay

2900 Bayport Drive Tampa FL

Free Cancellation

Reserve now, pay when you stay

$207 nightly

$235 total

Jan 25 - Jan 26

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 2 outdoor pools, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and concierge services and wedding services are also provided.

Pool

Pet friendly

DoubleTree by Hilton Tampa Rocky Point Waterfront

3050 N Rocky Point Dr W Tampa FL

$140 nightly

$158 total

Jan 25 - Jan 26

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 and free WiFi in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Pool

Pet friendly

Hotel South Tampa & Suites

3314 S Dale Mabry Hwy Tampa FL

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$104 total

Jan 25 - Jan 26

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.

Pool

Breakfast included

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3001 University Center Dr Tampa FL

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$132 total

Feb 17 - Feb 18

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

Hotel Tampa Riverwalk

200 N Ashley Dr Tampa FL

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$221 total

Jan 25 - Jan 26

Total with taxes and fees

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

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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.

Photos of local treasures

Browse Hillsborough County vacation photos for more inspiration

Tampa featuring a pond, a lake or waterhole and mangroves

Tampa which includes a park, a river or creek and a bridge

Lettuce Lake Park featuring a garden, a lake or waterhole and fall colors

Big Cat Rescue which includes zoo animals as well as a large group of people

Frequently asked questions

How much are vacation packages to Hillsborough County?

With offers starting from as little as $315, hotel and flight packages are an excellent way to stretch your vacation budget even further. Get ready Hillsborough County — here you come!

Where can I get the best vacation package deals for Hillsborough County?

For an amazing Hillsborough County package deal, book with Travelocity. Choose from 400 airlines and 1,000,000 worldwide properties to create your ultimate trip — the choice is all yours!

Why should I purchase my Hillsborough County vacation bundle via Travelocity?

We have experiences for every kind of traveler, first-rate service and 24/7 support. And to top it off, we'll match any better price you happen to find with our Price Match Guarantee.

Will I save money on my Hillsborough County car rental if I bundle it with a hotel or flight?

Certainly. And our Hillsborough County vacation packages are the best way to do it. With just a few clicks you can save cash and time by bundling your bookings. Pick up the keys to your rental car then chart your own course. Need to fill your itinerary? Add some tours or experiences to your package and save on those too.

Which airport is best for Hillsborough County?

For passengers contemplating flying in and out of Hillsborough County, the most commonly used airports are Tampa Intl. Airport (TPA), Sarasota-Bradenton Intl. Airport (SRQ) and St. Petersburg-Clearwater Intl. Airport (PIE).

What is there to do in Hillsborough County?

Hillsborough County boasts hidden gems around every turn, however make sure you see Raymond James Stadium and ZooTampa at Lowry Park while you're in town. These landmarks are a must-see for visitors to the region.