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.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,657, price is now CA $955 per person
CA $955
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,193 reviews)
Great place to stay! Friendly staff. Spacious suites. Pet friendly. Heated pool.

Reviewed on Jan 31, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Price was CA $2,779, price is now CA $1,663 per person
CA $1,663
per person
Apr 11 - Apr 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (2,355 reviews)
Furniture was very old/ dirty and couch was broken.

Reviewed on Jan 14, 2026

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,617, price is now CA $978 per person
CA $978
per person
Apr 11 - Apr 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (496 reviews)
The room was clean. Comfortable bed. Kitchenette. Beautiful view of the water. Can watch the birds. Close to stores, restaurant, St. Pete beach, Tampa bay, and old Tampa bay, and other sites. The city of St. Petersburg and Tampa.

Reviewed on Jan 24, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $2,295, price is now CA $1,469 per person
CA $1,469
per person
Apr 11 - Apr 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
Great room, great view and beach. Wonderful staff. I would stay here again.

Reviewed on Feb 6, 2026

John's Pass Hotel

John's Pass Hotel

2 out of 5
Price was CA $3,037, price is now CA $1,950 per person
CA $1,950
per person
Apr 11 - Apr 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (263 reviews)
Room was spotless. Great stay here. Great for a couple days vacation with enough to walk to including the beach. Will come back again.

Reviewed on Feb 3, 2026

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Highland Park Hotel Deals

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Feb 10 to Feb 11
CA $139
CA $156 total
Feb 10 - Feb 11
includes taxes & fees
7/10 Good! (1,005 reviews)
Kind and helpful staff. Clean room.

Reviewed on Jan 31, 2026

Howard Johnson by Wyndham Winter Haven FL
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
2953 Ridge Way Lake Wales FL
Fully refundable
The price is CA $201 per night from Feb 22 to Feb 23
CA $201
CA $225 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Clean, great staff, comfortable, great coffee!!!!

Reviewed on Feb 1, 2026

Holiday Inn Express Lake Wales N-Winter Haven by IHG
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is CA $320 per night from Feb 27 to Feb 28
CA $320
CA $412 total
Feb 27 - Feb 28
includes taxes & fees
9/10 Wonderful! (159 reviews)
Good

Reviewed on Feb 2, 2026

LEGOLAND Beach Retreat
See all 1,575 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

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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.