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.
The Avalon Club
CA $1,292
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (595 reviews)
Our family had a wonderful stay. The location was perfect. We also loved being able to use the hotels umbrellas, chairs & towels at the beach. The suite was more spacious than we expected! The sofa bed was not comfortable, but the regular beds were. Can’t beat the price for the room & view we had. We would absolutely come back!
Reviewed on Sep 21, 2026
Hotel South Tampa & Suites
Virginia Park
CA $1,193
per person
Dec 6 - Dec 13
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (1,881 reviews)
Todo excelente, el lugar está muy acorde al precio. Las chicas de recepción y la limpieza bastante amables y atentas. Desayuno variado. Buena ubicación. Ideal para cuando viajas solo.
Reviewed on Sep 22, 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 refundable
CA $154
CA $173 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"I love this hotel. All the staff was wonderful, personable and helpful. My room was fantastic. My bed was very comfortable and I will definitely use this hotel when I come back to Winterhaven. One last thing it’s very convenient to everything you need."
Reviewed on Sep 22, 2026
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
CA $171
CA $192 total
Sep 27 - Sep 28
includes taxes & fees
9.6/10 Exceptional! (1,367 reviews)
"."
Reviewed on Sep 22, 2026
Staybridge Suites Winter Haven Auburndale by IHG
305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
CA $182
CA $204 total
Sep 27 - Sep 28
includes taxes & fees
9.8/10 Exceptional! (911 reviews)
"I had a last-minute emergency for me to stay away from my local home for a couple of days. The check-in was so reassuring as it was last minute.. And the room... excellent. The property was extrememly clean, well appointed and I felt very safe as a single female. The breakfast and evening social ..."
Reviewed on Sep 22, 2026
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.
Inman Park
7.4/10 (14 reviews)
Inman Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? 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.
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.
Sertoma Park
6.6/10 (28 reviews)
Sertoma Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? 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 $934 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.
