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

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
I took my two kids for a getaway weekend trip before school starts and we had the best time! My building was at a perfect spot. I was close to the pool area and the water park. I loved that everything was walkable. My kids and I really enjoyed the shops and the Waterpark was so fun! The wave pool was great, along with the water slides and lazy river.. overall, it was a great trip and our room was very nice as well. I definitely recommend.

Reviewed on Jul. 28, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
Awesome stay! Pool is amazing and staff is friendly!

Reviewed on Jul. 27, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (518 reviews)
A very clean hotel. Well worth the money for that fact alone.

Reviewed on Jul. 28, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Fantastic hotel. Beautiful room, great food, exceptional staff and the smell was phenomenal

Reviewed on Jul. 27, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
The only thing that was a problem was the fact that I wasn't told that I couldn't use the water park unless I was a owner, other than that I love The place

Reviewed on Jul. 27, 2025

Ready to book your vacation to Highland City?

 

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Highland City Hotel Deals

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 CA $78 per night from Jul 30 to Jul 31
CA $78
CA $87 total
Jul 30 - Jul 31
includes taxes & fees
6.2/10 (1,063 reviews)
"I adore the front desk staff!"

Reviewed on Jul. 23, 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 CA $127 per night from Aug 3 to Aug 4
CA $127
CA $143 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Only problem I had was with the curtains closing completely in the corner windows which left us slightly exposed. We worked around it so I still gave it 5 stars."

Reviewed on Jul. 22, 2025

Holiday Inn Winter Haven by IHG
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 CA $174 per night from Jul 30 to Jul 31
CA $174
CA $195 total
Jul 30 - Jul 31
includes taxes & fees
9.6/10 Exceptional! (456 reviews)
"Really great experience, we will stay again"

Reviewed on Jul. 26, 2025

Staybridge Suites Winter Haven Auburndale by IHG
See all 1,461 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Discover the most popular places to visit in Highland City

Bryant Stadium

Explore the great outdoors at Bryant Stadium, a lovely green space in Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.

Bryant Stadium

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

Playground

Dinosaur World Theme Park

CA $37
per adult
Dinosaur World Theme Park
See all activities in Highland City

Frequently asked questions

How much does a Highland City vacation package cost?
You'll find cheap prices from CA $684 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?

  1. Choose your travel dates: What you'd like to do in Highland City and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.