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 $1,010, price is now CA $652 per person
CA $652
per person
Jul 30 - Aug 3
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (79 reviews)
The room was a little noisy from the air conditioner and outside noise. The shower was way to high.

Reviewed on Jun 19, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $1,802, price is now CA $1,180 per person
CA $1,180
per person
Aug 27 - Aug 31
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
No reviews
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,607, price is now CA $1,802 per person
CA $1,802
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,020 reviews)
Was a great stay overall, great staff very attentive to everything and professional, the location is great walk-able to restaurants and right in front of the beach, very clean and equipped rooms, only reason it doesn't get a five star is cause the amenities close to early and have no food available to buy at property.

Reviewed on Jun 23, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,564, price is now CA $1,087 per person
CA $1,087
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,149 reviews)
The room cleaning service lacked greatly! The floors were not even swept, the blankets were simply thrown up on the bed and the dirty towels picked up and new ones thrown on the counter! The floors had hair on them in the bathroom upon arrival.

Reviewed on Jun 23, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,866, price is now CA $2,014 per person
CA $2,014
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (532 reviews)
We had the best time! This is a perfect spot for a family trip!

Reviewed on Jun 22, 2026

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Winter Haven 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 $156 per night from Jul 5 to Jul 6
CA $156
CA $174 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Stay elsewhere! Housekeeping never came. Hotel smelled like weed. No microwave in room. Dailey per person charge for breakfast."

Reviewed on Jun 22, 2026

Holiday Inn 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 $265 per night from Jul 19 to Jul 20
CA $265
CA $352 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (271 reviews)
"Great experience!!!"

Reviewed on Jun 22, 2026

LEGOLAND Beach Retreat
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 $169 per night from Jun 29 to Jun 30
CA $169
CA $189 total
Jun 29 - Jun 30
includes taxes & fees
9.4/10 Exceptional! (1,309 reviews)
"Love it"

Reviewed on Jun 22, 2026

Best Western Plus Winter Haven Inn & Suites 
See all 37,706 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winter Haven

LEGOLAND® Florida

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

Northgate Shopping Center

You can search for that perfect souvenir at Northgate Shopping Center during your stay in Cypress Gardens. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Northgate Shopping Center

What to do in Winter Haven

LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

CA $151
per traveller
LEGOLAND Florida FasTrack Pass
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.