Highland Park Vacations from $634

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $930, price is now $634 per person
$634
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)

IRB Intercoastal

IRB Intercoastal

2.5 out of 5
Price was $1,393, price is now $850 per person
$850
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
No reviews

CW Resort

CW Resort

4 out of 5
Price was $1,485, price is now $995 per person
$995
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)

Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Rocky Point
Price was $1,196, price is now $809 per person
$809
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (5,285 reviews)

Holiday Inn Tampa Westshore - Airport Area by IHG

Holiday Inn Tampa Westshore - Airport Area by IHG

3 out of 5
Westshore
Price was $1,048, price is now $713 per person
$713
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,482 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Highland Park
View all trips

What to do in Highland Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$33
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

$87
per traveler
LEGOLAND Florida FasTrack Pass
See all activities in Highland Park

Highland Park 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
Fully refundable
$118 nightly
The price is $132 total per night from Nov 24 to Nov 25
$132 total
Nov 24 - Nov 25
Total with taxes and fees
Holiday Inn Winter Haven by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
8.6/10 Excellent! (220 reviews)
"Great for the kids"

Reviewed on Nov 12, 2026

Get rates
Legoland Florida Hotel
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $137 total per night from Nov 17 to Nov 18
$137 total
Nov 17 - Nov 18
Total with taxes and fees
Best Western Plus Winter Haven Inn & Suites 
See all 1,438 properties in Highland Park
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Highland Park vacation package cost?
You can pick up a vacation package to this top destination from $634 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.