Winter Haven Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,240, price is now CA $1,208 per person
CA $1,208
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
Loved the property will stay again

Reviewed on Nov 11, 2026

CW Resort

CW Resort

4 out of 5
Price was CA $2,616, price is now CA $1,525 per person
CA $1,525
per person
Jan 22 - Jan 29
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)

Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Save 100% on your flight
Price was CA $2,019, price is now CA $1,249 per person
CA $1,249
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (742 reviews)
It was a great location for the beach, dinner, and awesome spot to just hang out on the property! Beautiful beautiful place!!

Reviewed on Nov 9, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Price was CA $2,593, price is now CA $1,633 per person
CA $1,633
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (958 reviews)
Parking is $52 per night. Ugh. No bellman service. Awkward entry points with steps.

Reviewed on Nov 6, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,913, price is now CA $1,209 per person
CA $1,209
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,532 reviews)
Nicely renovated. Clean and convenient.

Reviewed on Nov 10, 2026

Ready to book your vacation to Winter Haven?

 

Choose your dates

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 $167 per night from Nov 24 to Nov 25
CA $167
CA $188 total
Nov 24 - Nov 25
includes taxes & fees
Holiday Inn Winter Haven by IHG
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 $173 per night from Nov 17 to Nov 18
CA $173
CA $194 total
Nov 17 - Nov 18
includes taxes & fees
Best Western Plus Winter Haven Inn & Suites 
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
The price is CA $190 per night from Nov 29 to Nov 30
CA $190
CA $213 total
Nov 29 - Nov 30
includes taxes & fees
Staybridge Suites Winter Haven Auburndale by IHG
See all 39,540 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

Stay near popular Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 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.
See properties

What to do in Winter Haven

LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

CA $122
per traveller
LEGOLAND Florida FasTrack Pass
See all activities in Winter Haven

Frequently asked questions

How much does a Winter Haven vacation package cost?
You'll find cheap prices from CA $1,208 on Expedia for your Winter Haven escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
You can typically find lower rates and greater availability in September, October and November. Check out our cheap Winter Haven vacation packages and you could get some great off-season discounts.
How many days is enough for Winter Haven?
Dedicate around 2 days for your Winter Haven vacation to really discover all that makes this place special. Explore popular areas, including Cypress Gardens and Jan Phyl Village. Then make a beeline for top attractions like Auburndale City Park and Theatre Winter Haven. With a good itinerary, you'll be kept busy with room for some downtime too. Want to venture outside of Winter Haven? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Winter Haven?
Whether you're looking to visit top attractions like Chain of Lakes Park and Theatre Winter Haven on your Winter Haven vacation, or coming for its great fishing, walking trails and golfing, there's something for everyone here. With so much to do, you'll soon find out why so many visitors think Winter Haven is a good vacation destination.
How to find the best Winter Haven package deals?
Start your search for a Winter Haven package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winter Haven package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winter Haven adventure off to a flying start.
Is it cheaper to book a Winter Haven vacation as a package?
You can enjoy significant savings on your next Winter Haven break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winter Haven?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Winter Haven getaway.
How to plan a trip to Winter Haven?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Winter Haven.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodations will probably be the largest expense during your trip to Winter Haven.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Winter Haven. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Winter Haven vacation package that brings all your bookings together.

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