Highland Park Vacations from $565

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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 $835, price is now $565 per person
$565
per person
Jun 23 - Jun 28
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (78 reviews)
This is an old school Florida motel. It is clean and quaint. It's not the Hilton, but that's the draw. Convenient location.

Reviewed on Apr 20, 2026

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,734, price is now $1,143 per person
$1,143
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (531 reviews)
It was actually perfect. Amazing beach, amazing spacious room. One of our new top picks for vacay spots.

Reviewed on Apr 30, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $840, price is now $566 per person
$566
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,196 reviews)
Loved the location and the roof top pool and bar!!

Reviewed on May 6, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,285, price is now $880 per person
$880
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (953 reviews)
Great stay! I don’t even want divulge the details of how great this place is because I want it to remain a hidden gem.

Reviewed on May 7, 2026

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $1,176, price is now $817 per person
$817
per person
Jul 22 - Jul 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (662 reviews)
We enjoyed our stay here and highly recommend it to anyone traveling to the area. The staff was super helpful. Parking does get overcrowded due to the pickleball courts and volleyball courts but we always had a place to park. The Skybar is a good place to enjoy a cold beverage and take in the view!

Reviewed on May 7, 2026

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Discover the most popular places to visit in Highland Park

Bok Tower Gardens

Bok Tower Gardens

4.5/5(66 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
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

5/5(1 review)

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

$39
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Horse Petting

Central Florida Adventure Park - Authentic Dude Ranch Experience

$25
per adult
Central Florida Adventure Park - Authentic Dude Ranch Experience
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
$114 nightly
The price is $128 total per night from Jun 7 to Jun 8
$128 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
Place was great and walking distance from two wonderful restaurants. Staff was friendly and very hospitable. Would definitely recommend

Reviewed on May 7, 2026

Holiday Inn Winter Haven by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
$308 nightly
The price is $345 total per night from May 13 to May 14
$345 total
May 13 - May 14
Total with taxes and fees
8.8/10 Excellent! (117 reviews)
In room treasure hunt was great, kids loved the disco elevator, food was ok. Lots of maintenance going on, screw loose in door, staff not as pleasant as I would think for a kids/family focused resort.

Reviewed on May 5, 2026

Legoland Florida Hotel
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 May 31 to Jun 1
$155 total
May 31 - Jun 1
Total with taxes and fees
9.4/10 Exceptional! (1,253 reviews)
Great choice of hotel by us 🙂 lovely location, friendly welcoming staff, parking, self service breakfast, coffee and water available in the reception area daily, large room with walk in shower, small clothes hanging area but sufficient for our stay, drawers, sofa bed in our room too, fridge, microwave ...

Reviewed on May 6, 2026

Best Western Plus Winter Haven Inn & Suites 
See all 1,485 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 $565 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.