Winter Haven Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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 S$178 per night from 13 Jul to 14 Jul
S$178
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (876 reviews)
Relaxing Stay
"I had a very relaxing time during my stay at Best Western"

Reviewed on 8 Jul, 2025

Best Western Plus Winter Haven Inn & Suites 
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 S$182 per night from 21 Jul to 22 Jul
S$182
21 Jul - 22 Jul
includes taxes & fees
9.6/10 Exceptional! (411 reviews)
10 out of 10
"This stay was beyond my expectations. Cleanliness, quality, service, even the breakfast was on point. Will definitely return int the future."

Reviewed on 7 Jul, 2025

Staybridge Suites Winter Haven Auburndale by IHG
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 7 Aug to 8 Aug
S$129
7 Aug - 8 Aug
includes taxes & fees
9.4/10 Exceptional! (536 reviews)
"Property was stunning, clean, modern, chic, and the room was incredible. Pro tips: If you call in the evening (I called 14 times between 1015pm and 145am due to my flight being delayed, ensuring I could check in passed their posted 2pm cutoff) they probably won't answer and when questioned about ..."

Reviewed on 7 Jul, 2025

Kompose Boutique Resort at Theme Parks
See all 38,170 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.

Popular places to visit

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

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

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Go City: Orlando All-Inclusive Pass with Kennedy Space Center

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

S$280
per adult
84% of travellers recommend
Go City: Orlando All-Inclusive Pass with Kennedy Space Center
Ladies Luncheon Pontoon Tour

Ladies Luncheon Pontoon Tour (Gentleman welcome)

S$128
per adult
Ladies Luncheon Pontoon Tour (Gentleman welcome)
See all activities in Winter Haven

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.