Highland Park Vacations from $451

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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 $792, price is now $451 per person
$451
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Excellent customer service

Reviewed on Dec 14, 2025

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $933, price is now $519 per person
$519
per person
Mar 17 - Mar 22
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended

Reviewed on Jan 1, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $2,845, price is now $1,629 per person
$1,629
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Staff was very accommodating and the Jr. Suite pleasant to come back to after my little adventures.

Reviewed on Jan 10, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $2,867, price is now $1,693 per person
$1,693
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
We were pleasantly surprised with how clean the room was when we arrived and had everything we needed. The walk from our room to the beach was about 4 seconds... perfect.

Reviewed on Jan 10, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,776, price is now $1,073 per person
$1,073
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Staff was very courteous

Reviewed on Jan 7, 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

4.5/5(64 reviews)

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
Mr Gator, minding his own business

Camp Mack's River Resort Airboat Rides

Enjoy an outing to Camp Mack's River Resort Airboat Rides during your stay in Lake Wales. Wander the lakeside and gardens in this family-friendly area.

Camp Mack's River Resort Airboat Rides
Great place to get away from the concrete jungle in Florida. Kissimmee state park has great camp sites and canoeing! #FloridaCamping #Adventure #nature #green #weekendgetaway

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

What to do in Highland Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$63
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Highland Park

Highland Park Hotel Deals

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
2953 Ridge Way Lake Wales FL
Fully refundable
$122 nightly
The price is $137 total per night from Jan 18 to Jan 19
$137 total
Jan 18 - Jan 19
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Very friendly staff, clean rooms with everything you could need. Breakfast was the highlight - amazing spread with kind & attentive breakfast staff. Location was very convenient for our needs with several great food and coffee options nearby as well as Publix.

Reviewed on Jan 8, 2026

Holiday Inn Express Lake Wales N-Winter Haven by IHG
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
$145 nightly
The price is $163 total per night from Jan 12 to Jan 13
$163 total
Jan 12 - Jan 13
Total with taxes and fees
9.4/10 Exceptional! (1,106 reviews)
Clean

Reviewed on Jan 5, 2026

Best Western Plus Winter Haven Inn & Suites 
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
$303 nightly
The price is $340 total per night from Jan 12 to Jan 13
$340 total
Jan 12 - Jan 13
Total with taxes and fees
8.8/10 Excellent! (58 reviews)
Location, theming, activities were amazing

Reviewed on Jan 3, 2026

Legoland Florida Hotel
See all 1,570 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 $451 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.