Highland City Holidays

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Top Flight + Hotel Deals in Highland City

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

Seasons Florida Resort

2 out of 5
Price was €998, price is now €659 per person
€659
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9/10 Wonderful! (3,664 reviews)
Excelente hotel , volveremos

Reviewed on 12 Jul 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was €1,609, price is now €816 per person
€816
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Family oriented

Reviewed on 10 Jul 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was €1,102, price is now €673 per person
€673
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very good! (1,979 reviews)
Nice place family-friendly

Reviewed on 13 Jul 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was €1,191, price is now €740 per person
€740
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very good! (6,621 reviews)
The rooms were nice and clean. The staff was absolutely great. They made sure we had everything that we needed very helpful. My family will be doing it again.

Reviewed on 12 Jul 2026

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Price was €1,198, price is now €896 per person
€896
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very good! (10,103 reviews)
Have bed bugs

Reviewed on 12 Jul 2026

Top hotels in Highland City

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is €97 per night from 2 Aug to 3 Aug
€97
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,016 reviews)
"Dawn at check in was great. Best sheets and pillows too."

Reviewed on 12 Jul 2026

Holiday Inn Winter Haven by IHG
Comfort Inn & Suites Lakeland North I-4

Comfort Inn & Suites Lakeland North I-4

2.5 out of 5
3520 N Hwy 98 Lakeland FL
Fully refundable
The price is €92 per night from 28 Jul to 29 Jul
€92
28 Jul - 29 Jul
includes taxes & fees
8.8/10 Excellent! (864 reviews)
"good variety for breakfast. suite was great. two large tv.s would stay again. Pool was outside and fairly clean; good temp."

Reviewed on 10 Jul 2026

Comfort Inn & Suites Lakeland North I-4
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is €324 per night from 20 Jul to 21 Jul
€324
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (160 reviews)
"This hotel is not in the same location is the main building which was not emphasized at the time of booking traveling with small children and having to commute from there to go to the legoland park was not practical and convenient. I won’t be staying there . The price difference is not worth the ..."

Reviewed on 13 Jul 2026

Legoland Florida Hotel
See all 1,434 properties in Highland City
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.

What to do in Highland City

Winter Haven: Coffee, Tea & Dessert Food Tour

Winter Haven: Coffee, Tea & Dessert Food Tour

€115
per adult
Winter Haven: Coffee, Tea & Dessert Food Tour
Winter Haven: Guided Brunch Tour with Local Delicacies

Winter Haven: Guided Brunch Tour with Local Delicacies

€123
per adult
Winter Haven: Guided Brunch Tour with Local Delicacies
Winter Haven: Chef's Table and Wine Tasting Tour

Winter Haven: Chef's Table and Wine Tasting Tour

€230
per adult
Winter Haven: Chef's Table and Wine Tasting Tour
See all activities in Highland City

Frequently asked questions

How much does a Highland City holiday package cost?
Offering great value package deals from €659 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?

  1. 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.
  2. 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.
  3. 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.
  4. Bundle your accommodation and airfare: Once you've settled on your travel dates and duration, book the ideal Highland City holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.