Winter Haven Holidays

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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$180 per night from 3 Aug to 4 Aug
S$180
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (888 reviews)
"Our stay was excellent!! The room was so neat and smelled clean at all times. Very quiet as well! The breakfast was delicious. We HIGHLY RECOMMEND this Hotel! You will not regret it but instead, you will love it!"

Reviewed on 14 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 20 Jul to 21 Jul
S$182
20 Jul - 21 Jul
includes taxes & fees
9.6/10 Exceptional! (424 reviews)
"Amazing stay! Clean and amazing rooms. AC that will rock your socks off lol Will be coming back"

Reviewed on 13 Jul, 2025

Staybridge Suites Winter Haven Auburndale by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way, Winter Haven, FL
The price is S$469 per night from 30 Jul to 31 Jul
S$469
30 Jul - 31 Jul
includes taxes & fees
10/10 Exceptional! (3 reviews)
"I had six grandkids and they all love playing with the Legos! Very convenient having the theme park next-door. We were disappointed some of the things were closed, but overall, it was a good experience."

Reviewed on 2 Jul, 2025

Legoland Florida Hotel
See all 38,384 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$85
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
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.