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.
Hibiscus Suites - Gateway to Siesta Key
CA $966
per person
Nov 6 - Nov 13
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,425 reviews)
Property looks to be recently renovated. Nice pool, room is large and has a kitchenette. Only drawbacks I can think of were very minor. Blinds in bedroom could use black out curtains or something darker. So bring an eye mask. Pool closes at dusk which is a shame. Location is a few minutes drive to the main beaches. Great value, clean, and service from front desk and house keeping were very good.
Reviewed on Aug 29, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,480
per person
Nov 3 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.6/10 Exceptional! (1,173 reviews)
Property was very clean and well maintained. The unit was well equipped and stocked w/ laundry/dish detergent and plenty of towels.
Reviewed on Aug 28, 2026
Captiva Beach Resort
South Village
CA $1,238
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,300 reviews)
Our stay was perfect! The room was beautiful with good AC and very clean. Housekeeping went above and beyond. Very close to the beach and the free trolley to the village. It was very quiet and we enjoyed great sleeps. This was our second time here and I can only hope we get to come back again.
Reviewed on Aug 27, 2026
Ready to book your vacation to Winter Haven?
Winter Haven Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundableReserve now, pay when you stay
CA $122
CA $136 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Staff is friendly, close to many things"
Reviewed on Aug 29, 2026
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
CA $158
CA $178 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,355 reviews)
"The rooms very spacious and most of all the breakfast"
Reviewed on Aug 29, 2026
Staybridge Suites Winter Haven Auburndale by IHG
305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
CA $168
CA $188 total
Sep 6 - Sep 7
includes taxes & fees
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.
Stay near popular Winter Haven attractions
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.
Chain of Lakes Park
8.2/10 (185 reviews)
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.
Peppa Pig Theme Park Florida
Have a fun-filled day with the family at Peppa Pig Theme Park Florida during your visit to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Theatre Winter Haven
7.4/10 (56 reviews)
You can enjoy a show at Theatre Winter Haven during your trip to Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Cypresswood Golf and Country Club
6.4/10 (25 reviews)
Enjoy a round of golf in Winter Haven at Cypresswood Golf and Country Club. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Lake Henry Golf Club
6.0/10 (11 reviews)
Enjoy a round of golf in Winter Haven at Lake Henry Golf Club. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Willowbrook Golf Course
6.8/10 (15 reviews)
Enjoy a round of golf in Winter Haven at Willowbrook Golf Course. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Lake Region Golf Club
Enjoy a round of golf in Winter Haven at Lake Region Golf Club. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
What to do in Winter Haven
Frequently asked questions
How much does a Winter Haven vacation package cost?
You'll find cheap prices from CA $966 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?
- 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.
- 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.
- 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.
- 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.
