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 AED 503 per night from May 4 to May 5
AED 503
AED 563 total
includes taxes & fees
4 May - 5 May
9.4/10 Exceptional! (776 reviews)
"Staff was very friendly."

Reviewed on 16 April 2025

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 AED 465 per night from May 11 to May 12
AED 465
AED 521 total
includes taxes & fees
11 May - 12 May
9/10 Wonderful! (79 reviews)
"Na"

Reviewed on 19 April 2025

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 AED 375 per night from Apr 22 to Apr 23
AED 375
AED 420 total
includes taxes & fees
22 Apr - 23 Apr
6.8/10 (1,001 reviews)
"The rooms are very clean, nice rooms. Bed are ok,"

Reviewed on 6 April 2025

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 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)

Have a fun-filled day at LEGOLAND® Florida and find out why this is a popular theme park in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

LEGOLAND® Florida

Chain of Lakes Park

4/5(84 reviews)

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Chain of Lakes Park

Theatre Winter Haven

You can enjoy a show at Theatre Winter Haven during your trip to Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Theatre Winter Haven