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.
Westgate Lakes Resort & Spa Universal Studios Area
CA $793
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very good! (7,020 reviews)
The property is very large and our room was far from the lobby they say that they have shuttle buses to transport you to and from around the property but our stay was 5 days and it truly was difficult to get the shuttle buses to pick you up it’s also only cards on property no cash is allowed so that’s another thing that was a shock to us also there is only one dinner spot on property and the meals there are you well made other then that I would recommend this hotel .
Reviewed on Sep 21, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,274
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
We stayed with family for a few days and enjoyed everything about the resort and cottage!
Reviewed on Sep 21, 2026
Ready to book your vacation to Highland City?
Highland City Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
CA $154
CA $172 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Clean room and well maintained property. Convenient to where we had an event."
Reviewed on Sep 21, 2026
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
CA $278
CA $366 total
Sep 22 - Sep 23
includes taxes & fees
8.6/10 Excellent! (199 reviews)
"Great stay. Very easy to manage. Place is very clean. Staff is nice. Food was good."
Reviewed on Sep 21, 2026
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
CA $78
CA $97 total
Oct 12 - Oct 13
includes taxes & fees
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
Frequently asked questions
How much does a Highland City vacation package cost?
You'll find cheap prices from CA $793 on Expedia for your Highland City break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Highland City costs.
What are the cheapest months to go to Highland City?
If you're hoping to book a cheap Highland City vacation package, consider planning a trip in January, February and August. You'll typically find lower rates on hotels and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Highland City?
We suggest planning a Highland City vacation for a minimum of 2 days. This will allow you plenty of time to check off key attractions such as Family Fun Centre and Southgate Shopping Centre, as well as explore neighbourhoods like Lake Somerset and Lake Bentley. You could even slot in one or two day trips outside of Highland City.
How to find the best Highland City package deals?
Begin your search for a Highland City package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Highland City package deal straight away, simply switch up 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 underway.
Is it cheaper to book a Highland City vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels individually. Better still, you can customize your Highland City escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Highland City?
If you're planning a spontaneous Highland City vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Highland City?
- Choose your travel dates: What you'd like to do in Highland City and your preferred season can help you decide when to go.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will probably be the largest expense during your trip to Highland City.
- Decide how many days away: Start by listing all the attractions and activities you'd like to get to in Highland City. Then, estimate how long you'll need for each, along with any travel time.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Highland City vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
