Highland Park Vacations from $1,020
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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.
The Avalon Club
$1,020
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (608 reviews)
Much more spacious than we expected. Very clean, entire staff were very friendly and knowledgeable. A nice scent was all over the hotel, a nice touch. Definitely would recommend this hotel.
Reviewed on Oct 23, 2026
Cedar Cove Resort and Cottages
$1,160
per person
Jan 15 - Jan 19
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (604 reviews)
Awesome resort, highly recommend if visiting AMI. Great location and can use free island trolley to go anywhere you want.
Reviewed on Oct 24, 2026
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Highland Park Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
$103 nightly
$115 total
Nov 23 - Nov 24
Total with taxes and fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
$249 nightly
$279 total
Nov 17 - Nov 18
Total with taxes and fees
8.6/10 Excellent! (212 reviews)
"Proximity to Legoland can't be beat - very convenient. Disappointed with check in - we were given a key card with a QR code on the back and were told that everything we need to know is on there. Couldn't find wifi password. Didn't find out about complimentary breakfast until our last day. Breakfast ..."
Reviewed on Oct 23, 2026
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
$122 nightly
$137 total
Oct 27 - Oct 28
Total with taxes and fees
9.6/10 Exceptional! (1,378 reviews)
"My family and I enjoyed our stay here. The guy that checked us in was very helpful and accommodating. The hotel itself and the room was very clean as well. There were a few breakfast items to choose from which we enjoyed. The only thing was that they had a better selection on Saturday than Sunday ..."
Reviewed on Oct 23, 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 $1,020 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.
