Winter Haven Vacations from ₩328,187

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The Latest Winter Haven Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Tampa Fairgrounds/Casino

Wyndham Garden Tampa Fairgrounds/Casino

2 out of 5
per person
Oct 27 - Oct 29
found 8 hours ago
Roundtrip flight included
New York (LGA) to Tampa (TPA)
8.6/10 Excellent! (8 reviews)
Clean, good location.

Reviewed on Aug 5, 2025

Hampton Inn & Suites Tampa Northwest/Oldsmar

Hampton Inn & Suites Tampa Northwest/Oldsmar

2.5 out of 5
per person
Oct 27 - Oct 29
found 8 hours ago
Roundtrip flight included
New York (LGA) to Tampa (TPA)
9.2/10 Wonderful! (1,000 reviews)
Great customer service

Reviewed on Aug 3, 2025

Holiday Inn Express & Suites Ruskin by IHG

Holiday Inn Express & Suites Ruskin by IHG

2.5 out of 5
per person
Oct 27 - Oct 29
found 8 hours ago
Roundtrip flight included
New York (LGA) to Tampa (TPA)
9.6/10 Exceptional! (1,007 reviews)
Great stay option, no doubt.

Reviewed on Aug 4, 2025

Seminole Hard Rock Hotel & Casino Tampa

Seminole Hard Rock Hotel & Casino Tampa

4 out of 5
per person
Oct 27 - Oct 29
found 8 hours ago
Roundtrip flight included
New York (LGA) to Tampa (TPA)
8.8/10 Excellent! (1,360 reviews)
Good place to stay for a weekend. Only issue I had was the overbearing smell of smoke inside the casino. Literally burning my eyes.

Reviewed on Aug 3, 2025

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
per person
Oct 27 - Oct 29
found 8 hours ago
Roundtrip flight included
New York (LGA) to Tampa (TPA)
9.2/10 Wonderful! (1,022 reviews)
It was quiet! The pancake machine is my favorite.

Reviewed on Aug 3, 2025

Find the Best Winter Haven Vacation Packages

Winter Haven Hotel Deals

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 ₩175,891 per night from Aug 10 to Aug 11
₩175,891
₩196,998 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (471 reviews)
"It is a very brand new hotel. Nothing to complain. The room is very clean. We really like it!"

Reviewed on Aug 1, 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 ₩128,802 per night from Aug 17 to Aug 18
₩128,802
₩144,258 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Only problem I had was with the curtains closing completely in the corner windows which left us slightly exposed. We worked around it so I still gave it 5 stars."

Reviewed on Jul 22, 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 ₩175,406 per night from Aug 10 to Aug 11
₩175,406
₩196,456 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (934 reviews)
"Great location if you plan to go to Legoland/Peppa Pig park. It was very clean and breakfast was great"

Reviewed on Aug 4, 2025

Best Western Plus Winter Haven Inn & Suites 
See all 37,729 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.

Discover the most popular places to visit in Winter Haven

Legoland Florida which includes a pond, a river or creek and rides

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

Sertoma Park

Sertoma Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Sertoma Park

Frequently asked questions

How much does a Winter Haven vacation package cost?
You'll find cheap prices from ₩328,187 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.