Winter Haven Vacations

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Find the Best Winter Haven Vacation Packages

Winter Haven Hotel Deals

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 NT$4,158 per night from May 18 to May 19
NT$4,158
NT$4,657 total
includes taxes & fees
May 18 - May 19
9.4/10 Exceptional! (783 reviews)
"Clean, updated and nicely designed property and rooms. Breakfast was good with a variety of options (eggs, potatoes, sausage, biscuits, bagels, cereal, oatmeal etc.) The only drawback was there does not seem to be enough soundproofing because we could hear everything; doors being slammed shut, people ..."

Reviewed on 2025/4/22

Best Western Plus Winter Haven Inn & Suites 
Home2 Suites By Hilton Winter Haven
Home2 Suites By Hilton Winter Haven
3 out of 5
6015 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NT$4,258 per night from May 18 to May 19
NT$4,258
NT$4,769 total
includes taxes & fees
May 18 - May 19
9/10 Wonderful! (82 reviews)
"We were bringing our family to Legoland, and as presented, Legoland is literally right outside the door. The front desk staff was very helpful and a significant plus in giving us a good feeling about the hotel and our stay. Our kids had a great time in the pool, breakfast was good, but the overall ..."

Reviewed on 2025/4/21

Home2 Suites By Hilton Winter Haven
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St, SW, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is NT$3,317 per night from Apr 28 to Apr 29
NT$3,317
NT$3,715 total
includes taxes & fees
Apr 28 - Apr 29
6.8/10 (1,002 reviews)
"Great"

Reviewed on 2025/4/23

Howard Johnson by Wyndham Winter Haven FL
See all 38,330 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.

Frequently asked questions

How much does a Winter Haven vacation package cost?
You’ll find cheap prices on Expedia for your Winter Haven getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
You can generally find reduced prices and better availability in September, October and November. Explore 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 if you’re hoping to enjoy everything that makes this place unique. Stroll around popular neighborhoods, including Cypress Gardens and Jan Phyl Village. Then tick off top attractions like Indigo’s Billiards, Bowling & Games and Indigo’s Family Fun Center. With a good itinerary, you’ll be kept busy with room for some downtime too. Want to travel outside of Winter Haven? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Winter Haven?
Popular for its fishing, walking trails and golfing, a Winter Haven vacation is a hit with all kinds of visitors. Be sure to check out top sights like Chain of Lakes Park and Theatre Winter Haven, and consider renting a set of wheels for day trips to explore even more.
How to find the best Winter Haven package deals?
Use Expedia’s filters to find some of the best Winter Haven package deals. When you start your search, simply set your maximum budget and then sort the results by “Price: low to high.” If you want to save, plan your adventure for midweek, or search for Winter Haven package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it’s usually best to lock in your vacation package well in advance.
Is it cheaper to book a Winter Haven vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can tailor your Winter Haven trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winter Haven?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Winter Haven getaway.
How to plan a trip to Winter Haven?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Winter Haven.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Winter Haven. Then, pick a hotel that matches your budget, whether that’s an affordable option or a lavish retreat.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to experience in Winter Haven. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Winter Haven vacation package.

Discover the most popular places to visit in Winter Haven

Legoland Florida which includes a pond, a river or creek and rides

LEGOLAND® Florida

4.5/5(1,082 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.

LEGOLAND® Florida

Northgate Shopping Center

4.5/5(3 reviews)

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

Inman Park

5/5(4 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.

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