Highland City Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Highland City
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundableReserve now, pay when you stay
S$121
6 Sept - 7 Sept
includes taxes & fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
S$262
21 Aug - 22 Aug
includes taxes & fees
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
S$92
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (423 reviews)
"One of the most disappointing parts of our stay was when I asked if it was possible to change the date of one of our reserved nights\. It was simply a date mistake, not a cancellation, and we were still planning to stay at the hotel\. Unfortunately, the initial response was an immediate “no,” with ..."
Reviewed on 6 Aug, 2026
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 Highland City holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Highland City costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Highland City?
January, February and August are great times to search for cheap Highland City holiday packages. Travelling in quieter periods means you can generally find reduced prices on accommodation and flights.
How many days is enough for Highland City?
The ideal duration for your Highland City holiday depends on what you'd like to see. Usually, a few days to a week will give you enough time to hit all the main attractions and discover some hidden gems along the way.
How to find the best Highland City package deals?
Start your search for a Highland City package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Highland City package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Highland City adventure off to a flying start.
Is it cheaper to book a Highland City holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking hotels and flights separately. Better still, you can tailor your Highland City escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Highland City?
If you're planning an impromptu Highland City adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Highland City?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Highland City.
- Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may come up during your trip to Highland City.
- Decide how long to go away for: Now that you're more familiar with Highland City, you can figure out the right length of your break. Pull together a rough plan and give yourself enough time to get through everything on your must-do list.
- Bundle your accommodation and airfare: Once you've settled on your travel dates and duration, book the ideal Highland City holiday package for you.
* 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.
