Hillsborough County Holidays

Photo by Geraldine Soh

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Top destinations in Hillsborough County

Tampa Bay featuring night scenes, a river or creek and skyline
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Tampa

Tampa
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Plant City

Plant City

Hillsborough County Flight & Hotel Packages

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

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
7 Sept - 14 Sept
found 18 hours ago
Return flight included
New York (NYC) to Orlando (MCO)
8.2/10 Very Good! (5,121 reviews)
Great staff and breakfast

Reviewed on 14 Jul, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
7 Sept - 14 Sept
found 18 hours ago
Return flight included
New York (NYC) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
The outlooks of the property is good however the facilities are too old. No room cleaning services makes me so upsets.

Reviewed on 14 Jul, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
7 Sept - 14 Sept
found 18 hours ago
Return flight included
New York (JFK) to Orlando (MCO)
8.2/10 Very Good! (5,060 reviews)
The property was good and nice but the water park in some areas were way too expensive

Reviewed on 15 Jul, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
7 Sept - 14 Sept
found 18 hours ago
Return flight included
New York (JFK) to Orlando (MCO)
8.8/10 Excellent! (2,970 reviews)
The staff was very accommodating and everything was very clean

Reviewed on 14 Jul, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
per person
7 Sept - 14 Sept
found 18 hours ago
Return flight included
New York (JFK) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Clean, quiet, professional staff and cute area. Just my style. Will definitely stay here again!

Reviewed on 14 Jul, 2025

Top hotels in Hillsborough County

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is S$220 per night from 7 Aug to 8 Aug
S$220
7 Aug - 8 Aug
includes taxes & fees
8.6/10 Excellent! (1,652 reviews)
"Nice overnight stay! Super comfortable"

Reviewed on 12 Jul, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Hotel Alba, Tapestry Collection by Hilton
Hotel Alba, Tapestry Collection by Hilton
4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is S$184 per night from 5 Aug to 6 Aug
S$184
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (1,991 reviews)
"Beautiful property except for only one working elevator due to hurricane damage Breakfast was delicious. Pool and bar are excellent"

Reviewed on 14 Jul, 2025

Hotel Alba, Tapestry Collection by Hilton
Sailport Waterfront Suites
Sailport Waterfront Suites
3.5 out of 5
2506 N Rocky Point Dr, Tampa, FL
The price is S$177 per night from 28 Jul to 29 Jul
S$177
28 Jul - 29 Jul
includes taxes & fees
8.2/10 Very Good! (4,613 reviews)
"This was a great place for a family vacation. There were plenty of activities near by and traffic was minimal. I will be rebooking another stay here for the future."

Reviewed on 11 Jul, 2025

Sailport Waterfront Suites
See all 4,017 properties in Hillsborough County
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.

Frequently asked questions

How much does a Hillsborough County holiday package cost?
Chart your own course with our Hillsborough County holiday packages, which start from only S$347. Select the hotels and flights that suit your travel style. Then, add on a few tours or experiences for an incredible escape.
How do I get a cheap travel package to Hillsborough County?
Browse and book everything in one place with our Hillsborough County holiday packages. You'll discover deals on hotels, flights and more that'll keep your credit card happy and your adventurousness alive. And, with more than 550 air carriers and 1,000,000 hotels around the globe to select from, you'll have endless opportunities to mix and match as you like.
Where should I stay in Hillsborough County?
Tampa is a great place to visit. It draws in many wanderers who come to explore its top sights, which include Raymond James Stadium and University of South Florida.
What are the top hotels in Hillsborough County?
For properties in Tampa with friendly service and cosy beds, you can't beat Hyatt Place Tampa Downtown and Seminole Hard Rock Hotel & Casino Tampa. If you're swinging by Plant City as well, you can look forward to a relaxing night's sleep at Ramada by Wyndham Tampa Westshore or Hampton Inn & Suites Tampa Airport Avion Park Westshore.
How far in advance should I book my Hillsborough County holiday?
Reserving your tickets early with Expedia means one less thing to have to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. Usually, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Hillsborough County sometimes become available just a few weeks before departure.
What does an Expedia Hillsborough County travel package include?
Expedia has everything you need to plan your Hillsborough County trip, but what goes into your package is your call. Pick from any combination of flights, hotels and rental cars. Looking for some activities or tours to keep you busy? Once you've made your booking, you can add them on too. Whatever your style, there's a holiday package to match your needs.
What should I know before booking a Hillsborough County travel package?
An Expedia travel package can be customized for your circumstances and is a great way to stretch your dollars further. How much you include is completely up to you. Rental cars, hotels and flights --- decide on a combination that suits your style.
Can I choose my airline with a Hillsborough County Expedia holiday package?
Yes, and with over 550 airlines to choose from around the world, you've got lots of choice. Browse the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Hillsborough County holiday package?
Certainly, and we're here to help. You may be able to cancel or amend your Hillsborough County holiday package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If life throws you a curveball, browse our Customer Service Portal for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.