Winter Haven Trips (flight + hotel)

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Top hotels in Winter Haven

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 P7,245 per night from Aug 14 to Aug 15
P7,245
P8,115 total
Aug 14 - Aug 15
includes taxes & fees
9.6/10 Exceptional! (488 reviews)
"Very nice"

Reviewed on Aug 8, 2025

Staybridge Suites Winter Haven Auburndale by IHG
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 P5,306 per night from Sep 7 to Sep 8
P5,306
P5,942 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Excellent hotel
"This holiday Inn property was wonderful. Checkin was simple ,easy and I was given free food vouchers for my daughter for breakfast and dinner (with 1 adult paying adult. The breakfast was a full breakfast with all variety of items;Well worth it. Our room was clean and very spacious (1king bed & daybed ..."

Reviewed on Aug 6, 2025

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 P6,885 per night from Aug 17 to Aug 18
P6,885
P7,711 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (939 reviews)
"Great location. Great staff.. Clean, modern spacious rooms."

Reviewed on Aug 6, 2025

Best Western Plus Winter Haven Inn & Suites 
See all 38,265 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.

Popular places to visit

Legoland Florida featuring a park, rides and a pond

LEGOLAND® Florida

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

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.

Peppa Pig Theme Park Florida

Lake Henry Golf Club

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.

Lake Henry Golf Club

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

P3,862
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Winter Haven

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.

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