Winter Haven Holidays

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Top hotels in Winter Haven

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 €167 per night from 23 Feb to 24 Feb
€167
includes taxes & fees
23 Feb - 24 Feb
9.4/10 Exceptional! (716 reviews)
"The property is very good, and staff are very friendly. The only issue is the pool was cold."

Reviewed on 19 Feb 2025

Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is €127 per night from 2 Mar to 3 Mar
€127
includes taxes & fees
2 Mar - 3 Mar
6.8/10 (1,006 reviews)
"Very clean"

Reviewed on 20 Feb 2025

Howard Johnson by Wyndham Winter Haven FL
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is €188 per night from 23 Mar to 24 Mar
€188
includes taxes & fees
23 Mar - 24 Mar
8/10 Very Good! (6,918 reviews)
"Loved this property and so did the kids will definitely be back."

Reviewed on 20 Feb 2025

The Grove Resort & Water Park Orlando
See all 38,196 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 holiday 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 holiday 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 holiday 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 holiday if you’re hoping to enjoy everything that makes this place unique. Stroll around popular neighbourhoods, including Cypress Gardens and Jan Phyl Village. Then tick off top attractions like Indigo’s Billiards, Bowling & Games and Indigo’s Family Fun Centre. 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 holiday package to Winter Haven?
Popular for its fishing, walking trails and golfing, a Winter Haven holiday 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 holiday package well in advance.
Is it cheaper to book a Winter Haven holiday as a package?
An Expedia holiday 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 holiday 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 customised Winter Haven holiday package.

Popular places to visit

Legoland Florida featuring a river or creek, a pond and rides

LEGOLAND® Florida

4.5/5(7 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

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 visit its top-notch restaurants.

Lake Henry Golf Club

Sertoma Park

Explore the great outdoors at Sertoma Park, a lovely green space in Winter Haven. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

Sertoma Park

What to do in Winter Haven

Go City: Orlando All-Inclusive Pass with Kennedy Space Center

Go City: Orlando All-Inclusive Pass with Kennedy Space Center

€192
per adult
84% of travellers recommend
Go City: Orlando All-Inclusive Pass with Kennedy Space Center
See all activities in Winter Haven
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.