Winter Haven Vacation Packages

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Your Winter Haven Vacation

When a city getaway is calling, answer it with a Winter Haven vacation package. The neighborhood of Fussels Corner, which is great for golfing, nature and walking, makes a fantastic base for your adventures. You'll want to take in some sights during your trip to Winter Haven. Carve out some time for popular attractions like LEGOLAND® Florida, Chain of Lakes Park and Auburndale City Park. Don't put off visiting this destination any longer. The perfect Winter Haven vacation is just a few clicks away with Expedia.

Top Winter Haven 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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Winter Haven 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
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is CA $423 per night from Mar 5 to Mar 6
CA $423
CA $527 total
Mar 5 - Mar 6
includes taxes & fees
8.8/10 Excellent! (65 reviews)
Room clean kids loved bunkbeds Staff helpful

Reviewed on Feb 1, 2026

Legoland Florida Hotel
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 39,811 properties in Winter Haven
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 Winter Haven

Legoland Florida featuring a pond, a garden and a river or creek

LEGOLAND® Florida

4.5/5(72 reviews)

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

LEGOLAND® Florida
Scenic view of Winter Park, Chain of Lakes canal. The Chain of Lakes is a popular tourist destination for residents and visitors to Winter Park, Florida, USA.

Chain of Lakes Park

3/5(1 review)

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Chain of Lakes Park

Indigo's Family Fun Center

Enjoy a stop at Indigo's Family Fun Center, an entertaining place to visit in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Indigo's Family Fun Center

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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.