Winter Haven Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 4 Dec to 5 Dec
S$180
includes taxes & fees
4 Dec - 5 Dec
9.4/10 Exceptional! (614 reviews)
"Close to legoland and the staff are amazing and very friendly. The breakfast options were great too."

Reviewed on 30 Nov,2024

Best Western Plus Winter Haven Inn & Suites 
Holiday Inn Winter Haven, an IHG Hotel
Holiday Inn Winter Haven, an IHG Hotel
3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is S$148 per night from 8 Dec to 9 Dec
S$148
includes taxes & fees
8 Dec - 9 Dec
8.8/10 Excellent! (1,003 reviews)
"It was a nice place with nice people that made aure we were happy and comfortable."

Reviewed on 3 Dec,2024

Holiday Inn Winter Haven, an IHG Hotel
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 6 Dec to 7 Dec
S$153
includes taxes & fees
6 Dec - 7 Dec
6.8/10 (1,004 reviews)
"Great location. Just need to improve on their breakfast options"

Reviewed on 30 Nov,2024

Howard Johnson by Wyndham Winter Haven FL
See all 37,350 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 holiday package cost?
Maybe less than you might think — from just , actually! By bundling flights, hotels and car rentals into your own custom-built package, your Winter Haven escape is just a few clicks away.
How do I get a cheap travel package to Winter Haven?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we’ve got them all covered. Select a combination that best fits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 hotel options worldwide, which lets you customize your Winter Haven adventure.
Where should I stay in Winter Haven?
If this is your first visit to Winter Haven, you’ll love Cypress Gardens. This vibrant neighbourhood is home to some excellent attractions, such as LEGOLAND® Florida.
What are the top hotels in Winter Haven?
If you’re thinking of staying in the Cypress Gardens neighbourhood, some great options are Winter Haven Gardens Inn and Holiday Inn Winter Haven, an IHG Hotel. Jan Phyl Village is also a popular Winter Haven area. We recommend Courtyard by Marriott Winter Haven or Econo Lodge Winter Haven Chain Of Lakes if you choose this end of town.
How far in advance should I book my Winter Haven holiday?
Be rewarded with the biggest variety and the cheapest prices by booking your holiday to Winter Haven nice and early. Airlines tend to release flight tickets around 12 months before departure, so reserve your spot as soon as possible. That said, Expedia is committed to giving you the best bargains around, so it’s always a good time to book your dream holiday!
What does an Expedia Winter Haven travel package include?
Travel packages include flights, hotels and rental cars, but you can combine any of them to create your dream Winter Haven holiday. You can also add on fun things like tours and activities once you’ve made your booking. You’re the boss! When you bundle your bookings with Expedia, you’ll get access to discounts you won’t find anywhere else.
What should I know before booking a Winter Haven travel package?
So many places to wander around, so many things to see. With a package, you’ll be able to check more of them off your list. Combine your flights, hotels and rental cars and land big savings.
Can I choose my airline with a Winter Haven Expedia holiday package?
Yes, and with over 550 airlines to choose from globally, you’re spoiled for choice. Browse the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Winter Haven holiday package?
Yes you can, and we’ll help you every step of the way. You may be able to amend or cancel your Winter Haven holiday package at no cost within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company if your booking is older than that. If your travel plans unexpectedly change, take a look at our Customer Service Portal for further information.

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$106
Per adult
84% of travellers recommend
LEGOLAND® Florida Tickets
Go City: Orlando All-Inclusive Pass with 25+ Attractions

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

S$267
Per adult
84% of travellers recommend
Go City: Orlando All-Inclusive Pass with Kennedy Space Center
One hour Pontoon Boat Cruise of The Chain of Lakes

One hour Historical Wildlife Boat Cruise of The Chain of Lakes

S$36
Per adult
100% of travellers recommend
One hour Historical Wildlife Boat Cruise of The Chain of Lakes
See all activities in Winter Haven

* 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.