Highland Park Vacations from $350

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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $574, price is now $350 per person
$350
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep 2, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,330, price is now $720 per person
$720
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
We were very pleased with our 3 night stay at the hotel. The staff graciously offered us an umbrella and chairs to take to the beach from the donation stash. We really appreciated that and returned the items when we left for future guests.

Reviewed on Sep 8, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $1,117, price is now $658 per person
$658
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (23 reviews)
This property was recently acquired in July by new owners & they are in the process of renovations. The 1st night there, we were cooking dinner in the microwave & it blew the fuse for the microwave and fridge. Staff was very quick to keep us on the bottom level as requested but move us to another room. 2nd room AC didn't cool properly, and I called the afterhours number and they made sure that maintenance was there at 6am (earliest possible) to replace the unit with one that worked. Hotel was super clean. Staff & Owners were GREAT. Location is very convenient & walkable to everything local. 1 street away from beachfront.

Reviewed on Sep 13, 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,540, price is now $962 per person
$962
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,411 reviews)
Clean and beautiful beach

Reviewed on Sep 7, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,847, price is now $1,154 per person
$1,154
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,600 reviews)
Great location for families and a wonderful hotel

Reviewed on Sep 14, 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

4.5/5(64 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
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

$69
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Highland Park

Highland Park Hotel Deals

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
$135 nightly
The price is $151 total per night from Sep 18 to Sep 19
$151 total
Sep 18 - Sep 19
Total with taxes and fees
9.6/10 Exceptional! (546 reviews)
"I really enjoyed our stay. We enjoyed the pool area and the grills too. The rooms were nice and clean and any questions or thing we need was answered and attended to quickly."

Reviewed on Sep 6, 2025

Staybridge Suites Winter Haven Auburndale by IHG
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
$93 nightly
The price is $104 total per night from Sep 28 to Sep 29
$104 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Good location but be prepared to pay for it.
"This hotel has a great location (in this occasion). Rather pricey but it was clean and the staff was very friendly. But the fact that breakfast is not included was a real disappointment. It was $11.99 per day and it didn't include anything that other hotels includes in the pricing. WiFi and free ..."

Reviewed on Sep 9, 2025

Holiday Inn Winter Haven by IHG
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
$124 nightly
The price is $139 total per night from Sep 16 to Sep 17
$139 total
Sep 16 - Sep 17
Total with taxes and fees
9.4/10 Exceptional! (978 reviews)
Great hotel, clean and comfortable!
"This was a very nice hotel, clean and comfortable, with a friendly staff and a great breakfast! The room was spacious and clean, and very quiet!"

Reviewed on Sep 7, 2025

Best Western Plus Winter Haven Inn & Suites 
See all 1,563 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.

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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 $350 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.