Highland Park Vacation Packages

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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!

Top Highland Park Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,252, price is now CA $825 per person
CA $825
per person
Jun 15 - Jun 20
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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 Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $1,610, price is now CA $927 per person
CA $927
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,191 reviews)
What a beautiful hotel. Excellent customer service. Great location. Rooftop bar is top notch

Reviewed on Apr 25, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $3,311, price is now CA $2,195 per person
CA $2,195
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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

DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

4 out of 5
Price was CA $1,951, price is now CA $1,316 per person
CA $1,316
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,006 reviews)
The staff very friendly and helpful. Especially Dinah and Stacy (Lifeguard). The meals were above and beyond. The house keeping staff were wonderful.

Reviewed on May 3, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $1,710, price is now CA $1,156 per person
CA $1,156
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,158 reviews)
Cutting board, bread knife were missing. Kettle was offered on request.

Reviewed on Apr 24, 2026

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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
The price is CA $161 per night from May 31 to Jun 1
CA $161
CA $180 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Overall a great stay. The room was great. On site gym was a little sparse for my taste, but we made it work. Was disappointed that breakfast was an 11.99 buffet. I'm from the area and there are better options nearby.

Reviewed on May 2, 2026

Holiday Inn Winter Haven by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is CA $598 per night from Jun 4 to Jun 5
CA $598
CA $723 total
Jun 4 - Jun 5
includes taxes & fees
8.8/10 Excellent! (116 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
The price is CA $191 per night from May 31 to Jun 1
CA $191
CA $214 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,250 reviews)
Room was very large and nice. Breakfast meal was limited but adequate Staff was helpful and polite

Reviewed on May 4, 2026

Best Western Plus Winter Haven Inn & Suites 
See all 1,483 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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Discover the most popular places to visit in Highland Park

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

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

What to do in Highland Park

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Horse Petting

Central Florida Adventure Park - Authentic Dude Ranch Experience

CA $34
per adult
Central Florida Adventure Park - Authentic Dude Ranch Experience
See all activities in Highland Park

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.