Highland Park Vacations from $694

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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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,029, price is now $694 per person
$694
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (506 reviews)
The staff was so sweet and accommodating. Everything you could need for an overnight at the beach. Room by the road had traffic noise but we didn’t mind at all!

Reviewed on May 7, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,962, price is now $1,303 per person
$1,303
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (3,211 reviews)
We had a fabulous Mother’s Day weekend at Wyndham Grand Clearwater Beach. It also happened to be Country Weekend, which made the experience even more fun and memorable. The entertainment was a huge plus and created such an amazing atmosphere throughout the weekend. The lobby bar staff and pool staff were absolutely amazing. Everyone was so attentive, friendly, and welcoming, especially on Mother’s Day. They truly went above and beyond to make all the moms feel special and taken care of. From the beautiful property to the great energy and outstanding customer service, the entire experience exceeded our expectations. Thank you to the whole team for making our Mother’s Day celebration so enjoyable and unforgettable. We will definitely be back!

Reviewed on May 12, 2026

East Gulf Dockside Beach Homes

East Gulf Dockside Beach Homes

2.5 out of 5
Save 100% on your flight
Price was $1,300, price is now $893 per person
$893
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
No reviews
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,172, price is now $805 per person
$805
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,005 reviews)
Really enjoyed our stay. This is convenient to the beach and boardwalk.

Reviewed on May 10, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $1,151, price is now $798 per person
$798
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,245 reviews)
The 2 bedroom condo was very clean and updated. The walk to the beach was short and we didn't have to cross any busy streets just walked the small roads within the complex of other resort condos.

Reviewed on May 8, 2026

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Discover the most popular places to visit in Highland Park

Bok Tower Gardens

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

$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
$101 nightly
The price is $113 total per night from May 17 to May 18
$113 total
May 17 - May 18
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
Front staff was great

Reviewed on May 9, 2026

Holiday Inn Winter Haven by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
$296 nightly
The price is $332 total per night from May 19 to May 20
$332 total
May 19 - May 20
Total with taxes and fees
8.8/10 Excellent! (119 reviews)
Highly recommended! We went for My 6 year old son’ birthday and he had such a blast. Staff was amazing at all times. We will be coming back very soon. 🙏❤️

Reviewed on May 12, 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
$127 nightly
The price is $142 total per night from May 17 to May 18
$142 total
May 17 - May 18
Total with taxes and fees
9.4/10 Exceptional! (1,262 reviews)
Good for families

Reviewed on May 12, 2026

Best Western Plus Winter Haven Inn & Suites 
See all 1,481 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 $694 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.