Highland Park Vacations from $359

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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.
SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $607, price is now $359 per person
$359
per person
Mar 8 - Mar 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (417 reviews)
Great amenities, great staff

Reviewed on Jan 29, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,883, price is now $965 per person
$965
per person
Mar 11 - Mar 18
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

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,359, price is now $779 per person
$779
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Amazing all around! Very impressed.

Reviewed on Jan 25, 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,247, price is now $750 per person
$750
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7/10 Good! (1,744 reviews)
The hotel was nice. The service in the restaurant was excellent. We loved having close access to the River Walk.

Reviewed on Jan 21, 2026

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,415, price is now $872 per person
$872
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Clean and easy to check in

Reviewed on Jan 30, 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
$154 nightly
The price is $172 total per night from Feb 1 to Feb 2
$172 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
The room was clean and quiet. The staff were friendly. The only negative to the stay was the elevators weren’t working but I understand things happen and we were able to use the maintenance elevator. All in all a great stay and we would definitely stay at the IHG in Winter Haven again!

Reviewed on Jan 30, 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
$158 nightly
The price is $177 total per night from Feb 15 to Feb 16
$177 total
Feb 15 - Feb 16
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 Feb 3 to Feb 4
$105 total
Feb 3 - Feb 4
Total with taxes and fees
7/10 Good! (1,002 reviews)
Front deak staff was very polite and efficient. The room was okay, could have been cleaner, there were cigarette bitts all over the patio outside and some garbage left in the room.

Reviewed on Jan 27, 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 $359 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.