Highland Park Vacations from $657
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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!
The Latest Highland Park vacation packages
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
$735
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,173 reviews)
Loved the place, I was so impressed how clean it was. Beach view is perfect.
Reviewed on Sep 4, 2026
Cedar Cove Resort and Cottages
$1,527
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (584 reviews)
The room was immaculate and the beds and pillows were the comfiest I have ever slept in. The room had everything we needed to make our stay comfortable. The location is perfect and the beach there is amazing. We have stayed here 4 times now and will be back again. This is a small, locally owned resort and they take great pride in the property. We absolutely love it.
Reviewed on Sep 3, 2026
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Highland Park Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
$105 nightly
$118 total
Sep 20 - Sep 21
Total with taxes and fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
$248 nightly
$278 total
Sep 9 - Sep 10
Total with taxes and fees
8.6/10 Excellent! (188 reviews)
"Perfect for kids, good lunch also can’t beat the free breakfast"
Reviewed on Sep 2, 2026
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
$118 nightly
$132 total
Sep 7 - Sep 8
Total with taxes and fees
9.6/10 Exceptional! (1,368 reviews)
"Everything was nice and clean. The staff were friendly and I will be returning for future visits."
Reviewed on Sep 4, 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.
Find the Best Highland Park Vacation Packages
Highland Park Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 230 |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | Tiger Creek Preserve, Jump Florida Skydiving and KICCO Wildlife Management Area |
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Frequently asked questions
How much does a Highland Park vacation package cost?
You can pick up a vacation package to this top destination from $657 on Expedia. However, how much your vacation to Highland Park costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Highland Park?
If you'd like to snag a cheap Highland Park vacation package, consider visiting in May, June and July. You'll typically find better rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Highland Park?
Typically, a handful of days is enough to check out the main sights during your Highland Park vacation. However, if you want to have more time to rest or take day tours, think about extending your trip.
How to find the best Highland Park package deals?
Start your search for a Highland Park package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Highland Park package deal right away, just 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 Park getaway off to a flying start.
Is it cheaper to book a Highland Park vacation as a package?
You can enjoy significant savings on your next Highland Park break by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Highland Park?
If you're considering an impromptu Highland Park trip, check out 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 sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Highland Park vacation packages?
If you're anything like us, you love traveling the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Highland Park trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
