Highland Park Vacations from $567

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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.
Blue Wave Suites

Blue Wave Suites

2 out of 5
Price was $850, price is now $567 per person
$567
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (50 reviews)
The room was clean and perfect. Great location and a great place to stay!! Loved the outdoor balcony and so easy to check in and check out with the kiosk

Reviewed on Nov 1, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was $1,110, price is now $621 per person
$621
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (4,000 reviews)
Wonderful hotel with nice beachfront location equipped with cabanas to relax on. The on site restaurant Ocean Hai serves excellent dinner with special emphasis on seafood.

Reviewed on Nov 6, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,283, price is now $807 per person
$807
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (614 reviews)

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,161, price is now $751 per person
$751
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,409 reviews)
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating

Reviewed on Nov 7, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $925, price is now $615 per person
$615
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
The hole property was very clean the staff was always cleaning doors, floors, windows everything.The room was great. The only dislike was the pool closing at dark.

Reviewed on Nov 6, 2026

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What to do in Highland Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$33
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

$87
per traveler
LEGOLAND Florida FasTrack Pass
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
$118 nightly
The price is $132 total per night from Nov 15 to Nov 16
$132 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
"Spacious, comfortable and clean room. Conveniently located. Excellent for an fairly good price."

Reviewed on Nov 6, 2026

Holiday Inn Winter Haven by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
$249 nightly
The price is $279 total per night from Nov 17 to Nov 18
$279 total
Nov 17 - Nov 18
Total with taxes and fees
8.6/10 Excellent! (215 reviews)
"Para ser Halloween no habían los caramelos para los niños, tuvimos que salir a Walmart a comprarles, el desayuno es un solo plato dirigido para la habitación Muy poca disponibilidad de Legos para comprar adentro del hotel 😅 Y la dificultad principal es la demora de los ascensores Las habitaciones ..."

Reviewed on Nov 6, 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
$130 nightly
The price is $146 total per night from Nov 15 to Nov 16
$146 total
Nov 15 - Nov 16
Total with taxes and fees
9.6/10 Exceptional! (1,384 reviews)
"Exceptional place to stay. Staff very cordial, room very modern and clean and overall facility very eye pleasing."

Reviewed on Nov 6, 2026

Best Western Plus Winter Haven Inn & Suites 
See all 1,457 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 $567 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.