Highland City Vacation Packages
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Your Highland City Vacation
With plenty of highlights as well as some hidden gems, this city is best explored with a Highland City vacation package. Find a place to stay in Downtown Lakeland, which is good for shopping, bars and pubs and cafes. A trip to Highland City is a great opportunity to do a bit of sightseeing. Check out big-name attractions such as The Circle B Bar Reserve, The Club at Eaglebrooke and Horney Park. Check out Expedia's wide range of travel options and start organizing your ultimate vacation to Highland City today.
Top Highland City Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Price was CA $1,515, price is now CA $909 per person
CA $909
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (505 reviews)
Most of the staff was very helpful. Our rooms were clean and well kept. We were close to the parks.
Reviewed on Jun 7, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Price was CA $2,584, price is now CA $1,626 per person
CA $1,626
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Loved everything about it.
Reviewed on Jun 8, 2026
The Marker
Price was CA $3,276, price is now CA $2,140 per person
CA $2,140
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!
Reviewed on Apr 12, 2026
The Delaney Hotel
South Orange
Price was CA $1,932, price is now CA $1,265 per person
CA $1,265
per person
Aug 2 - Aug 9
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Orlando (MCO)
9.6/10 Exceptional! (1,114 reviews)
Very nice, small hotel and comfortable. It was convenient to the Amtrak train station. The restaurant served good foods and good drinks and had good service. The registration clerks and housekeeping staff were good. All staff members that I encountered were pleasant and greeted me. Whenever I come back into town and ride the train and need to be near the station I would definitely stay here again.
Reviewed on Jun 15, 2026
Highland City Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is CA $159 per night from Jul 5 to Jul 6
CA $159
CA $179 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Breakfast isn't included, which wasn't clear on booking"
Reviewed on Jun 8, 2026
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Jul 14 to Jul 15
CA $98
CA $123 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (350 reviews)
"Easy checkin"
Reviewed on Jun 13, 2026
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
The price is CA $458 per night from Jun 16 to Jun 17
CA $458
CA $567 total
Jun 16 - Jun 17
includes taxes & fees
8.8/10 Excellent! (132 reviews)
"Had a great time, loved the whole experience"
Reviewed on Jun 14, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
