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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was €1,532, price is now €526 per person
€526
per person
1 Nov - 8 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Great Hotel, really nice employees, but the pool is warm... on hot days you want to go and cool yourself down, but here you can't the pool is warm.

Reviewed on 20 Aug 2025

ette hotel

ette hotel

5 out of 5
Price was €1,965, price is now €1,063 per person
€1,063
per person
1 Nov - 8 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on 11 Aug 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was €1,229, price is now €668 per person
€668
per person
1 Nov - 8 Nov
found 12 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
Always a good time there.

Reviewed on 22 Aug 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was €912, price is now €584 per person
€584
per person
1 Nov - 8 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.8/10 Excellent! (3,048 reviews)
For some reason i really liked the towels. So many towels

Reviewed on 22 Aug 2025

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Price was €945, price is now €650 per person
€650
per person
1 Nov - 8 Nov
found 12 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very Good! (1,433 reviews)
It is DIRECTLY on the beach and by the famous sign. I was shocked at the amount of homeless people in the area. I did not feel comfortable going to the beach at night. Heard a few arguments and yelling late at night on the street. The staff tho….. AMAZING

Reviewed on 20 Aug 2025

Top hotels in Highland City

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW, Winter Haven, FL
Fully refundable
The price is €121 per night from 3 Sept to 4 Sept
€121
3 Sept - 4 Sept
includes taxes & fees
9.6/10 Exceptional! (507 reviews)
"It was very good"

Reviewed on 17 Aug 2025

Staybridge Suites Winter Haven Auburndale by IHG
Howard Johnson by Wyndham Lakeland

Howard Johnson by Wyndham Lakeland

2.5 out of 5
939 W. Robson St., I-4 Exit 32, Lakeland, FL
Fully refundableReserve now, pay when you stay
The price is €62 per night from 24 Aug to 25 Aug
€62
24 Aug - 25 Aug
includes taxes & fees
6.4/10 (1,102 reviews)
"Great breakfast! To go breakfast, coffee all day!"

Reviewed on 19 Aug 2025

Howard Johnson by Wyndham Lakeland
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 €83 per night from 1 Sept to 2 Sept
€83
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Easy check-in"

Reviewed on 18 Aug 2025

Holiday Inn Winter Haven by IHG
See all 1,472 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.

Popular places to visit

The Circle B Bar Reserve

The Circle B Bar Reserve

Explore the great outdoors at The Circle B Bar Reserve, a lovely green space in Lakeland. Visit the shops and top-notch restaurants in this family-friendly area.

The Circle B Bar Reserve
Polk Museum of Art

Polk Museum of Art

You can spend time studying the exhibits at Polk Museum of Art during your travels in Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.

Polk Museum of Art

Lakeside Village

4/5(1 review)

You can find the perfect gifts to bring home at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.

Lakeside Village

What to do in Highland City

Picture 2 for Activity Tampa: Haunted Train Depot Ghost Adventure

Tampa Bay Area: VIP Haunted Train Depot Ghost Adventure

€46
per adult
Tampa Bay Area: VIP Haunted Train Depot Ghost Adventure
See all activities in Highland City

Frequently asked questions

How much does a Highland City holiday package cost?
Offering great value package deals from €526 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.

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