Highland Park Vacations from $424

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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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $694, price is now $424 per person
$424
per person
Jan 22 - Jan 25
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
18.4/10 Exceptional! (4,612 reviews)
Room and areas we clean and very quiet. I would stay again.

Reviewed on Nov 16, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,679, price is now $926 per person
$926
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (466 reviews)
Very nice stay. Would stay there again.

Reviewed on Nov 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,492, price is now $844 per person
$844
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
19.2/10 Exceptional! (707 reviews)
The unit was excellent. The price for these accommodations was very reasonable. It had two bedrooms and two full bathrooms. There was a washed and dryer, full well stocked kitchen, living/ dining area and a large patio. The appliances were spotless and looked brand new. Everything worked perfectly. There are large screen easy to use TV's in each bedroom and the living area. The staff was super friendly and helpful. The swimming pool was very well kept and clean. The outdoor spa was exceptional. Parking was great. We have been traveling since 2000 in many locations around the USA and other countries. These were by far the best accommodations we have experienced. Wonderful experience and an exceptional staff! When we return to this area we will stay here.

Reviewed on Nov 14, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,734, price is now $1,037 per person
$1,037
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
18.4/10 Exceptional! (1,001 reviews)
Great front desk staff ! Very kind and helpful

Reviewed on Oct 27, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,423, price is now $901 per person
$901
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,006 reviews)
Would definitely stay here again .

Reviewed on Oct 31, 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

$58
per traveler
84% 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
$112 nightly
The price is $125 total per night from Nov 30 to Dec 1
$125 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Simple and direct, you get what you pay for

Reviewed on Nov 14, 2025

Holiday Inn Winter Haven by IHG
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
$144 nightly
The price is $161 total per night from Nov 19 to Nov 20
$161 total
Nov 19 - Nov 20
Total with taxes and fees
9.6/10 Exceptional! (639 reviews)
Hotel was very clean and quiet. Beds were amazing. Will stay here again

Reviewed on Nov 15, 2025

Staybridge Suites Winter Haven Auburndale by IHG
Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven

3 out of 5
6015 Cypress Gardens Blvd Winter Haven FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $155 total per night from Nov 25 to Nov 26
$155 total
Nov 25 - Nov 26
Total with taxes and fees
9.4/10 Exceptional! (231 reviews)
Great

Reviewed on Nov 10, 2025

Home2 Suites By Hilton Winter Haven
See all 1,560 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 $424 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.