Highland Park Vacations from $458

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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 $794, price is now $458 per person
$458
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Excellent customer service

Reviewed on Dec 14, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,839, price is now $1,667 per person
$1,667
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
Best place on earth right on the Beach , quite relaxing and the staff is wonderful.Definitely be back .

Reviewed on Dec 22, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,944, price is now $1,784 per person
$1,784
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
We loved our stay here. Exceeded expectations

Reviewed on Dec 13, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,151, price is now $1,380 per person
$1,380
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Great hotel and very nice and clean rooms. We will definitely be back. Stunning beach view!!

Reviewed on Dec 24, 2025

Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $881, price is now $575 per person
$575
per person
Feb 5 - Feb 12
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (317 reviews)
Fast check in, nice room

Reviewed on Dec 23, 2025

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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
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
$130 nightly
The price is $146 total per night from Jan 25 to Jan 26
$146 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
All good.

Reviewed on Dec 20, 2025

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
$139 nightly
The price is $155 total per night from Jan 4 to Jan 5
$155 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,088 reviews)
Everything was great

Reviewed on Dec 24, 2025

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
$85 nightly
The price is $95 total per night from Dec 29 to Dec 30
$95 total
Dec 29 - Dec 30
Total with taxes and fees
6.8/10 (1,004 reviews)
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!

Reviewed on Dec 14, 2025

Howard Johnson by Wyndham Winter Haven FL
See all 1,564 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 $458 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.