Highland City Vacations from $267
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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.
The Latest Highland City vacation packages
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
$1,138
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms.
The staff at the main building were so helpful with our packages and printing documents for us.
Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort.
Overall, a great selection and would start again!
Reviewed on Sep 25, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
$2,122
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.6/10 Exceptional! (1,236 reviews)
Okay hotel but nowhere near the price premium that was paid, not sure how this hotel has such high reviews this was our most expensive reservation and left the most to be desired. Not a bad spot, but definitely not outstanding.
Reviewed on Oct 1, 2026
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View all tripsHighland City Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
$110 nightly
$123 total
Oct 6 - Oct 7
Total with taxes and fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
$205 nightly
$229 total
Oct 12 - Oct 13
Total with taxes and fees
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
$64 nightly
$71 total
Nov 2 - Nov 3
Total with taxes and 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.
Find the Best Highland City Vacation Packages
Highland City Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 10,800 |
Top Sights | Sun N Fun Air Museum, Florida Air Museum and Polk Museum of Art |
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Frequently asked questions
How much does a Highland City vacation package cost?
Offering great value package deals from $267 on Expedia, you'll be pleasantly surprised at how much a vacation 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?
You can generally find lower prices and better availability in May, June and July. Check out our cheap Highland City vacation packages and you could land some great off-season discounts.
How many days is enough for Highland City?
With a well-planned schedule, you can easily tick off the top Highland City attractions in a few days. But if you'd like to discover hidden gems or take day trips, consider booking your Highland City vacation for longer.
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 vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Highland City vacation packages?
Secure your dream trip to Highland City with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
