Highland City Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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 S$182 per night from 24 Aug to 25 Aug
S$182
24 Aug - 25 Aug
includes taxes & fees
9.6/10 Exceptional! (498 reviews)
"Clean, like new, friendly staff, beautiful large room, comfy beds"

Reviewed on 12 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 S$90 per night from 18 Aug to 19 Aug
S$90
18 Aug - 19 Aug
includes taxes & fees
6.4/10 (1,092 reviews)
"Construction"

Reviewed on 15 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 S$134 per night from 24 Aug to 25 Aug
S$134
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Excellent hotel
"This holiday Inn property was wonderful. Checkin was simple ,easy and I was given free food vouchers for my daughter for breakfast and dinner (with 1 adult paying adult. The breakfast was a full breakfast with all variety of items;Well worth it. Our room was clean and very spacious (1king bed & daybed ..."

Reviewed on 6 Aug, 2025

Holiday Inn Winter Haven by IHG
See all 1,474 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

Publix Field at Joker Marchant Stadium

Catch an event at Publix Field at Joker Marchant Stadium during your trip to Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.

Publix Field at Joker Marchant Stadium

Eastside Village Shopping Center

You can browse for the perfect souvenirs at Eastside Village Shopping Center during your trip to Lakeland. Amble around this family-friendly area's lakeside or attend a sporting event.

Eastside Village Shopping Center

Wing Chun Kung Fu Downtown Lakeland

Catch an event at Wing Chun Kung Fu Downtown Lakeland during your trip to Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.

Wing Chun Kung Fu Downtown Lakeland

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

S$67
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 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. 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.