Hillsborough County Vacation Packages 2025/2026 from $225

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.

The Shores Resort & Spa

$225

per person

Jan 4 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and complimentary bicycles are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$559

per person

Feb 20 - Feb 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Florida Hotel & Conference Center in the Florida Mall

$312

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.

Westgate Cocoa Beach Resort

$688

per person

Jan 4 - Jan 9

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.

Westgate Vacation Villas Resort

Save 100% on your flight

$451

per person

Feb 15 - Feb 22

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Top Hillsborough County hotels deals

DoubleTree by Hilton Tampa Rocky Point Waterfront

3050 N Rocky Point Dr W Tampa FL

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$139 total

Dec 18 - Dec 19

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

Hilton Tampa Airport Westshore

2225 N Lois Ave Tampa FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$105 total

Dec 22 - Dec 23

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

Hotel Tampa Riverwalk

200 N Ashley Dr Tampa FL

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$142 total

Dec 24 - Dec 25

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

Grand Hyatt Tampa Bay

2900 Bayport Drive Tampa FL

Free Cancellation

Reserve now, pay when you stay

$196 nightly

$222 total

Dec 21 - Dec 22

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

Hotel Alba, Tapestry Collection by Hilton

5303 W Kennedy Blvd Tampa FL

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$132 total

Dec 30 - Dec 31

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

$76 nightly

$87 total

Nov 30 - Dec 1

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

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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 $225, 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.