Highland Park Vacations from $544

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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $886, price is now $544 per person
$544
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,012 reviews)
Room was very clean.

Reviewed on Mar 29, 2026

Voyager Beach Club

Voyager Beach Club

2.5 out of 5
Sunshine Beach
Price was $987, price is now $585 per person
$585
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (109 reviews)
Everything about this resort was perfect! Can't wait to go back!

Reviewed on Dec 30, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $922, price is now $596 per person
$596
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,192 reviews)
Absolutely everything was perfect from check in to food and drink, staff, and amenities. 1000% will be back when visiting the area

Reviewed on Apr 4, 2026

Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,187, price is now $823 per person
$823
per person
May 14 - May 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,010 reviews)
We loved our stay and wil return! The pool was a little dirty at times and there were black bugs flying around a lot and in the pool and all over the sidewalks near the pool. The blue paint from the lounge chairs ruined two bathing suits and my new purse :(

Reviewed on Apr 4, 2026

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Discover the most popular places to visit in Highland Park

Bok Tower Gardens

Bok Tower Gardens

Bok Tower Gardens is just one of the places to see in Lake Wales, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Bok Tower Gardens
Spanish moss hanging from trees at Lake Kissimmee Park, Florida.

Lake Kissimmee State Park

You can take time to visit Lake Kissimmee State Park during your travels to Lake Wales. Wander the lakeside and gardens in this family-friendly area.

Lake Kissimmee State Park
Grand Hotel

Grand Hotel

Find out about the history of Lake Wales when you take a trip to Grand Hotel. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Grand Hotel

What to do in Highland Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$39
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Horse Petting

Central Florida Adventure Park - Authentic Dude Ranch Experience

$25
per adult
Central Florida Adventure Park - Authentic Dude Ranch Experience
See all activities in Highland Park

Highland Park Hotel Deals

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
$136 nightly
The price is $152 total per night from Apr 12 to Apr 13
$152 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (1,192 reviews)
Absolutely everthing was wonderful. Staff was very friendly, polite, kind and respectful. Fun play area outside for kids to play, pool open until 9 pm, which is great for the family. 4 min walk to dollar store for kids toys etc, as well as Publix 6 min walk. Legoland walking 10 min and that saved ...

Reviewed on Apr 5, 2026

Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Apr 8 to Apr 9
$114 total
Apr 8 - Apr 9
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Breakfast was good, room was clean and spacious and front desk staff was amazing. I left my phone at the front desk after checking in and the guy there ran it to my room for me.

Reviewed on Apr 2, 2026

Howard Johnson by Wyndham Winter Haven FL
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
$293 nightly
The price is $328 total per night from May 4 to May 5
$328 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (98 reviews)
Great stay! We will go back.

Reviewed on Mar 29, 2026

Legoland Florida Hotel
See all 1,514 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

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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 $544 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.