Winter Haven Holidays

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Top hotels in Winter Haven

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 2.507.092 ₫ per night from 16 Aug to 17 Aug
2.507.092 ₫
2.807.943 ₫ total
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Beautiful and clean rooms. The bed was so comfy. First hotel that I did not have to use my own soap, as they provided the brand I use! Staff was super friendly , this was the best experience I've had in a while!"

Reviewed on 28 Jul 2026

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 3.215.167 ₫ per night from 16 Aug to 17 Aug
3.215.167 ₫
3.600.987 ₫ total
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (1,353 reviews)
"STAFF WAS GREAT ROOM WAS SPACIOUS AND CLEAN"

Reviewed on 27 Jul 2026

Best Western Plus Winter Haven Inn & Suites 
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is 4.450.615 ₫ per night from 12 Aug to 13 Aug
4.450.615 ₫
6.017.020 ₫ total
12 Aug - 13 Aug
includes taxes & fees
8.8/10 Excellent! (325 reviews)
"The resort was pretty & family friendly. My family loved it & enjoyed our stay ❤️"

Reviewed on 29 Jul 2026

LEGOLAND Beach Retreat
See all 38,389 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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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.