Winter Haven Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to SAR 390 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 SAR 603 per night from Mar 30 to Mar 31
SAR 603
SAR 675 total
includes taxes & fees
30 Mar - 31 Mar
9.4/10 Exceptional! (732 reviews)
Great Hotel
"Needed a hotel immediately after the VRB was not up to standards. Place was very convenient to the venue we needed to attend. Very comfortable. Very friendly staff as well."

Reviewed on 9 March 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, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is SAR 414 per night from Apr 6 to Apr 7
SAR 414
SAR 464 total
includes taxes & fees
6 Apr - 7 Apr
6.8/10 (1,000 reviews)
Pleased
"We were very happy with our room and the property. We loved its proximity to legoland … the breakfast in the morning was just what we needed. We were very pleased."

Reviewed on 9 March 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 SAR 577 per night from Apr 13 to Apr 14
SAR 577
SAR 836 total
includes taxes & fees
13 Apr - 14 Apr
8/10 Very Good! (7,089 reviews)
"Stay was great overall. We were unable to get two units close to each other so that was hard. Both units were missing towels and garbage bags but staff eventually able to bring those. Property is well kept but parking limited for handicapped within the garages."

Reviewed on 12 March 2025

The Grove Resort & Water Park Orlando
See all 38,208 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

Winter Haven Hospital

Though Winter Haven Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Winter Haven while you are here.

Winter Haven Hospital