Highland City Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
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Highland City Flight & Hotel Packages

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

Palazzo Lakeside Hotel

3 out of 5
per person
10 Aug - 12 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Orlando (MCO)
8.2/10 Very Good! (5,078 reviews)
Loved the stay 10/10 recommend!!!

Reviewed on 30 Jun, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive
per person
10 Aug - 12 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Everything was just fantastic

Reviewed on 30 Jun, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
10 Aug - 14 Aug
found 1 day ago
Return direct flight included
San Francisco (SFO) to Orlando (MCO)
8/10 Very Good! (1,274 reviews)
I think that check out should be at 11am and check in 3pm. I would suggest for those who have a late flight, have some sort of changing area with a shower so that those who hang around waiting and use amenities such as pool and freshen up before headed to airport.

Reviewed on 1 Jul, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
11 Aug - 14 Aug
found 1 day ago
Return direct flight included
Oakland (OAK) to Orlando (MCO)
8.2/10 Very Good! (5,060 reviews)
We'll come back again

Reviewed on 30 Jun, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
per person
11 Aug - 14 Aug
found 1 day ago
Return direct flight included
Oakland (OAK) to Orlando (MCO)
8.8/10 Excellent! (2,916 reviews)
The staff was very friendly!

Reviewed on 30 Jun, 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 S$196 per night from 8 Jul to 9 Jul
S$196
8 Jul - 9 Jul
includes taxes & fees
9.6/10 Exceptional! (392 reviews)
"Good property and quality service"

Reviewed on 26 Jun, 2025

Staybridge Suites Winter Haven Auburndale by IHG
Best Western Plus Winter Haven Inn & Suites 
Best Western Plus Winter Haven Inn & Suites 
3.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is S$170 per night from 2 Jul to 3 Jul
S$170
2 Jul - 3 Jul
includes taxes & fees
9.4/10 Exceptional! (860 reviews)
"Bath tub stopper could only be opened with a butter knife."

Reviewed on 29 Jun, 2025

Best Western Plus Winter Haven Inn & Suites 
Extended Stay America Premier Suites Lakeland I4
Extended Stay America Premier Suites Lakeland I4
2.5 out of 5
4360 Lakeland Park Drive, Lakeland, FL
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 2 Jul to 3 Jul
S$121
2 Jul - 3 Jul
includes taxes & fees
7.6/10 Good! (1,004 reviews)
"I was surprised at the convenience. Very safe, move and friendly staff and guest. Totally recommend!"

Reviewed on 25 Jun, 2025

Extended Stay America Premier Suites Lakeland I4
See all 1,464 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.

Frequently asked questions

How much does a Highland City holiday package cost?
Offering great value package deals from S$380 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.

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

* 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.