Winter Haven Vacations

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Find the Best Winter Haven Vacation Packages

Winter Haven Hotel Deals

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL
Fully refundableReserve now, pay when you stay
₩119,724
₩134,091 total
Sep 6 - Sep 7
includes taxes & fees
Holiday Inn Winter Haven by IHG
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
₩162,025
₩181,468 total
Aug 9 - Aug 10
includes taxes & fees
Best Western Plus Winter Haven Inn & Suites 
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
₩146,543
₩164,128 total
Aug 9 - Aug 10
includes taxes & fees
9.8/10 Exceptional! (858 reviews)
"Definitely one of my favorite hotels ever. I love that it is located in the community so there are a lot of things that are walking distance. We were able to walk to the park and the local pizza place in a short distance. The staff were amazing. Every one was kind and helpful. The hotel is very clean ..."

Reviewed on Aug 6, 2026

Staybridge Suites Winter Haven Auburndale by IHG
See all 38,612 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.

Stay near popular Winter Haven attractions

A detailed model of a cityscape with various buildings, including a tall skyscraper, a modern building, and a historic building with a red roof.

LEGOLAND® Florida

9.0/10 (2,150 reviews)
LEGOLAND Florida Resort captivates families with 50+ rides and attractions for children aged 2-12. Explore themed worlds with interactive adventures, family-friendly coasters, and impressive LEGO replicas.
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A narrow water channel surrounded by lush greenery and tall trees.

Chain of Lakes Park

8.2/10 (185 reviews)
Navigate through 22 interconnected lakes in this serene Florida park, a haven for water enthusiasts. Rent a boat to explore the unique canal system connecting these diverse aquatic environments.
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Peppa Pig Theme Park Florida

The world's first Peppa Pig theme park offers rides and play areas designed for preschoolers. Families can enjoy Daddy Pig's Roller Coaster and meet beloved characters in this colorful, interactive environment.
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Theatre Winter Haven

7.4/10 (56 reviews)
Theatre Winter Haven delivers captivating community productions in an intimate setting with excellent acoustics. Secure tickets in advance to experience classic plays and musicals in this cultural cornerstone.
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Northgate Shopping Center

7.8/10 (35 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.
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Indigo's Family Fun Center

6.6/10 (19 reviews)
This laid-back entertainment venue combines bowling, billiards, and arcade games under one roof. Spend an evening challenging friends to friendly competition while enjoying drinks from the bar area.
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Lake Henry Golf Club

6.0/10 (11 reviews)
This private executive golf course offers a quick yet challenging par-60 layout with water hazards and quality Bermuda fairways. Members enjoy a relaxed round that can be completed in under three hours.
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Cypresswood Golf and Country Club

6.4/10 (25 reviews)
Designed by Ron Garl, this championship golf course challenges players amid Florida's natural landscape. Enjoy a round followed by live music and dining at the clubhouse on Thursday through Saturday evenings.
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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.

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