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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,289, price is now CA $739 per person
CA $739
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very good! (2,105 reviews)
I love everything about this place definitely going back

Reviewed on Nov 4, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was CA $2,679, price is now CA $1,354 per person
CA $1,354
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,677, price is now CA $924 per person
CA $924
per person
Jan 16 - Jan 23
found 19 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,589, price is now CA $1,439 per person
CA $1,439
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8.6/10 Excellent! (572 reviews)
Great place!

Reviewed on Nov 2, 2026

CW Resort

CW Resort

4 out of 5
Price was CA $2,538, price is now CA $1,439 per person
CA $1,439
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)

Ready to book your vacation to Highland City?

 

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Highland City Hotel Deals

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
The price is CA $165 per night from Nov 8 to Nov 9
CA $165
CA $185 total
Nov 8 - Nov 9
includes taxes & fees
Holiday Inn Winter Haven by IHG
Days Inn & Suites by Wyndham Lakeland

Days Inn & Suites by Wyndham Lakeland

2.5 out of 5
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Nov 30 to Dec 1
CA $87
CA $107 total
Nov 30 - Dec 1
includes taxes & fees
8.8/10 Excellent! (564 reviews)
"Great value! Was a little reluctant to book based on price and you usually get what you pay for, but the reviews after the remodel were excellent, so I took a chance and glad I did. Hotel was clean (including public restroom in the lobby), pool area was well-kept, breakfast area spotless. Front desk, ..."

Reviewed on Nov 4, 2026

Days Inn & Suites by Wyndham Lakeland
Howard Johnson by Wyndham Lakeland

Howard Johnson by Wyndham Lakeland

2.5 out of 5
939 W. Robson St. Lakeland FL
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Nov 9 to Nov 10
CA $80
CA $89 total
Nov 9 - Nov 10
includes taxes & fees
7.4/10 Good! (1,403 reviews)
"Its a Roach Motel!!!!!"

Reviewed on Nov 4, 2026

Howard Johnson by Wyndham Lakeland
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.
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What to do in Highland City

T-rex

Dinosaur World Plant City

CA $38
per adult
100% of travellers recommend
Dinosaur World Plant City
Ladies Luncheon Pontoon Tour

Ladies Luncheon Pontoon Tour (Gentleman welcome)

CA $141
per adult
Ladies Luncheon Pontoon Tour (Gentleman welcome)
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 $739 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.