Highland Park Vacations from $501

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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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $816, price is now $501 per person
$501
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good!

Reviewed on Feb 26, 2026

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,639, price is now $970 per person
$970
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Gym was well equipped and spacious, rooms were clean, kitchenette had all the things you would need, staff was super friendly and accommodating, and they have beach stuff that you can check out for free which was such a nice surprise. Plus the location is minutes from the beach with a rooftop view you can’t beat!

Reviewed on Mar 2, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,321, price is now $822 per person
$822
per person
May 25 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (837 reviews)
Beautiful property with stunning beach views . Very modern and clean units with all Possible amenities you could need. Very nice pool area and a stunning rooftop bar to watch the sunsets .

Reviewed on Mar 2, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,211, price is now $759 per person
$759
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Overall it was a good

Reviewed on Feb 17, 2026

Arvilla

Arvilla

2 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,221, price is now $768 per person
$768
per person
May 16 - May 23
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.2/10 Good! (24 reviews)
It was clean but small. Quiet atmosphere

Reviewed on Feb 23, 2026

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Discover the most popular places to visit in Highland Park

The 205 foot Neo-gothic 'singing tower' houses a 60-bell carillon – one of about 185 carillons in North America. Designed by Milton B. Medary, he was awarded in 1929 the American Institute of Architects gold medal for this design. #Trovember

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

$71
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
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
$135 nightly
The price is $151 total per night from Mar 22 to Mar 23
$151 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
Spotless and very courteous

Reviewed on Mar 2, 2026

Holiday Inn Winter Haven by IHG
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
$111 nightly
The price is $124 total per night from Apr 1 to Apr 2
$124 total
Apr 1 - Apr 2
Total with taxes and fees
7.2/10 Good! (1,005 reviews)
This place is gross. Very dirty the bathroom. Black hair in our towels. Mold in sink. Ledge around the sink. Pee stains down the toilet bottom of toilet. Just not clean at all.

Reviewed on Mar 2, 2026

Howard Johnson by Wyndham Winter Haven FL
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
$222 nightly
The price is $249 total per night from Mar 25 to Mar 26
$249 total
Mar 25 - Mar 26
Total with taxes and fees
9/10 Wonderful! (170 reviews)
Yes

Reviewed on Mar 1, 2026

LEGOLAND Beach Retreat
See all 1,542 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 $501 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.