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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,422, price is now CA $824 per person
CA $824
per person
May 9 - May 16
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
The property was perfect for pets. Big space to walk and off the main road.

Reviewed on Mar 23, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,351, price is now CA $1,460 per person
CA $1,460
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (846 reviews)
We enjoyed the pool area. Hotel was very quite, and very clean

Reviewed on Mar 24, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $1,792, price is now CA $1,186 per person
CA $1,186
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9/10 Wonderful! (1,193 reviews)
Everything was great

Reviewed on Mar 23, 2026

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Price was CA $1,969, price is now CA $1,318 per person
CA $1,318
per person
May 9 - May 16
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
2/10 (4 reviews)
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Price was CA $3,473, price is now CA $2,349 per person
CA $2,349
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
7.6/10 Good! (1,038 reviews)
Room was terrible! AC did not work, Bathroom door knob was barely hanging on. Toilet was nasty upon check in, checked out the next day and moved to another venue. Completely dissatisified!

Reviewed on Mar 23, 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 $152 per night from Apr 1 to Apr 2
CA $152
CA $170 total
Apr 1 - Apr 2
includes taxes & fees
7.2/10 Good! (1,008 reviews)
Clean, comfortable bed, and a hot shower

Reviewed on Mar 25, 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 $424 per night from Apr 19 to Apr 20
CA $424
CA $529 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (91 reviews)
Legoland was the best decision we ever made. If it weren’t for them our vacation would have been absolutely ruined. Expedia completely screwed up our bookings. We arrived after a an entire day of airports. Staff couldn’t have been better. The next day we woke up to a phenomenal breakfast only to ...

Reviewed on Mar 24, 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 $321 per night from Mar 26 to Mar 27
CA $321
CA $413 total
Mar 26 - Mar 27
includes taxes & fees
9/10 Wonderful! (183 reviews)
Everything was nice and clean

Reviewed on Mar 17, 2026

LEGOLAND Beach Retreat
See all 39,091 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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Family Vacations

Discover the most popular places to visit in Winter Haven

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

LEGOLAND® Florida

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

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

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Winter Haven

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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.