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.
Blue Wave Suites

Blue Wave Suites

2 out of 5
Price was CA $1,255, price is now CA $841 per person
CA $841
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Tampa (TPA)
9.6/10 Exceptional! (50 reviews)
The room was clean and perfect. Great location and a great place to stay!! Loved the outdoor balcony and so easy to check in and check out with the kiosk

Reviewed on Nov 1, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $1,416, price is now CA $895 per person
CA $895
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was CA $1,521, price is now CA $969 per person
CA $969
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Tampa (TPA)
9.4/10 Exceptional! (4,000 reviews)

CW Resort

CW Resort

4 out of 5
Price was CA $1,530, price is now CA $994 per person
CA $994
per person
Jan 29 - Feb 1
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)
This Hotel Has the Most Passive aggressive staff and owner I have ever encountered, They say yes while intentionally stalling, and practicing misleading information about the hotel, They use Subtle hostility, sarcasm, eye rolling and claiming misunderstanding of the situation . They play the victim and try to shift the blame elsewhere when called out. The Biggest is complaint I have is they absolutely HATE EXPEDIA travel site, I was told 5 times that since booked my vacation through EXPEDIA travel that I can't have house keeping every day, no use of some of the amenities and have to pay for use of going to the beach. Because I used a Discounter travel site (Expedia) This was Crazy !!!

Reviewed on Nov 7, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $1,794, price is now CA $1,203 per person
CA $1,203
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (615 reviews)

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 15 to Nov 16
CA $167
CA $187 total
Nov 15 - Nov 16
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 $184 per night from Nov 15 to Nov 16
CA $184
CA $206 total
Nov 15 - Nov 16
includes taxes & fees
9.6/10 Exceptional! (1,385 reviews)
"It was a great stay. We have no complaints and highly recommend this hotel."

Reviewed on Nov 7, 2026

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 $189 per night from Nov 29 to Nov 30
CA $189
CA $212 total
Nov 29 - Nov 30
includes taxes & fees
9.8/10 Exceptional! (935 reviews)
"Beautiful hotel, rooms, service, staff, beds, location!"

Reviewed on Nov 6, 2026

Staybridge Suites Winter Haven Auburndale by IHG
See all 39,489 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 $841 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.