Highland Park Vacations from $715
Book a Hotel + Flight or Car together to unlock savings
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.
ChartHouse Clearwater Beach Marina Hotel
$715
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,341 reviews)
Luckily, I was upgraded to a Harbor view beautiful room clean definitely recommend
Reviewed on Aug 13, 2026
Cedar Cove Resort and Cottages
$1,330
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (568 reviews)
Had an amazing time. Clean rooms, friendly staff. Amazing amenities with having use of beach chairs and umbrellas. Will return next summer.
Reviewed on Aug 13, 2026
The Westin Sarasota
Central Sarasota
$842
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,151 reviews)
My only gripe was the lack of an ocean view, had a view of the harbor/bay, which wasn’t bad, but was hoping for more
Reviewed on Aug 14, 2026
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Highland Park Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundableReserve now, pay when you stay
$88 nightly
$98 total
Sep 13 - Sep 14
Total with taxes and fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
$239 nightly
$268 total
Aug 23 - Aug 24
Total with taxes and fees
8.6/10 Excellent! (179 reviews)
"Great customer service!"
Reviewed on Aug 9, 2026
LEGOLAND Beach Retreat
100 Legoland Way SE Winter Haven FL
$179 nightly
$200 total
Aug 28 - Aug 29
Total with taxes and fees
8.8/10 Excellent! (359 reviews)
"La habitación no la limpiaron ni una sola vez solo cambiaron las toallas, lo demás aceptable , el desayuno fue el mismo todos los días , el servicio bueno."
Reviewed on Aug 14, 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 $715 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.