Highland Park Vacations from $444

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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 $691, price is now $444 per person
$444
per person
Mar 14 - Mar 18
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

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,280, price is now $839 per person
$839
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (2,509 reviews)
Clean room and pleasant staff

Reviewed on Jan 25, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,184, price is now $794 per person
$794
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Great staff perfect location for our stay.

Reviewed on Jan 27, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,891, price is now $1,975 per person
$1,975
per person
Mar 23 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
Clean room, friendly staff, great location, would definitely stay there again

Reviewed on Jan 26, 2026

Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Save 100% on your flight
Price was $1,633, price is now $1,131 per person
$1,131
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (1,804 reviews)
Awful breakfast but great location

Reviewed on Jan 18, 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

$63
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
Fully refundable
$135 nightly
The price is $151 total per night from Feb 1 to Feb 2
$151 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Yes they were

Reviewed on Jan 18, 2026

Holiday Inn Winter Haven by IHG
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
$147 nightly
The price is $165 total per night from Feb 18 to Feb 19
$165 total
Feb 18 - Feb 19
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
Very comfortable

Reviewed on Jan 25, 2026

Holiday Inn Express Lake Wales N-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
$93 nightly
The price is $105 total per night from Jan 30 to Jan 31
$105 total
Jan 30 - Jan 31
Total with taxes and fees
7/10 Good! (1,007 reviews)
Room was clean, the front desk lady very nice and it is so close to the Advent Health sports center. We'll be back again.

Reviewed on Jan 25, 2026

Howard Johnson by Wyndham Winter Haven FL
See all 1,571 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 $444 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.