Highland Park Vacation Packages
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- Plan, book, travel with confidence
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Your Highland Park Vacation
Save time and energy on your travel planning with a Highland Park vacation package. A good neighborhood to base yourself in this vibrant city is Cypress Gardens, which is good for families and much more besides. Bok Tower Gardens, Mountain Lake and KICCO Wildlife Management Area are just some of the many sights worth checking out during your trip to Highland Park. Expedia has what you need to escape your routine. Tailor your vacation to Highland Park to suit your style of travel, whatever that may be!
Top Highland Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,262
per person
Nov 28 - Dec 5
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,236 reviews)
We had an amazing time and loved our room! We loved the friendly staff and family friendly atmosphere without being too kid centered. Only thing we had trouble with were with our coffee maker not working, one TV not connecting to the internet and a dryer that we had to wait until Saturday to get someone to fix bec it was too late Friday night when we went to use it
Reviewed on Sep 27, 2026
Inn on the Beach - 18+ only
Pass-a-Grille
CA $1,318
per person
Nov 28 - Dec 5
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.8/10 Exceptional! (444 reviews)
The staff were very friendly and accommodating! The room was perfect for 4 and was super clean. We would definitely recommend and stay here again.
Reviewed on Sep 27, 2026
Ready to book your vacation to Highland Park?
Highland Park Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
CA $156
CA $174 total
Oct 4 - Oct 5
includes taxes & fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
CA $278
CA $367 total
Sep 29 - Sep 30
includes taxes & fees
8.6/10 Excellent! (203 reviews)
"We absolutely loved this hotel. It was full of exciting things for kids to do. My only complaint is the shower was cold."
Reviewed on Sep 27, 2026
LEGOLAND Beach Retreat
100 Legoland Way SE Winter Haven FL
CA $227
CA $310 total
Oct 12 - Oct 13
includes taxes & fees
8.6/10 Excellent! (380 reviews)
"Todo muy bonito."
Reviewed on Sep 27, 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.
What to do in Highland Park
Frequently asked questions
How much does a Highland Park vacation package cost?
You'll find cheap prices from CA $1,210 on Expedia for your Highland Park break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Highland Park costs.
What are the cheapest months to go to Highland Park?
January, February and July are the best times to look for cheap Highland Park vacation packages. Opting to travel in less busy periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Highland Park?
With a well-organized travel plan, you can easily hit the top Highland Park sights in a handful of days. But if you prefer to discover hidden gems or go on day tours, consider booking your Highland Park vacation for longer.
How to find the best Highland Park package deals?
Use Expedia's filters to find some unbeatable Highland Park package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Highland Park package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Highland Park vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Highland Park vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Highland Park?
If you're considering an impromptu Highland Park getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Highland Park?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Highland Park.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and activities. Your accommodations will probably be the biggest expense during your trip to Highland Park.
- Decide how long to go for: Now that you're more familiar with Highland Park, you can figure out the right length of your vacation. Pull together a draft plan and allocate enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Highland Park vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
