Winter Haven Holidays

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Top hotels in Winter Haven

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 S$167 per night from 31 May to 1 Jun
S$167
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Front staff was great

Reviewed on 9 May, 2026

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 S$197 per night from 31 May to 1 Jun
S$197
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (1,259 reviews)
great hotel stay right by legoland! the staff was very friendly in the hotel is extremely clean!

Reviewed on 9 May, 2026

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$196 per night from 31 May to 1 Jun
S$196
31 May - 1 Jun
includes taxes & fees
9.8/10 Exceptional! (779 reviews)
Large clean rooms, helpful Polite staff

Reviewed on 8 May, 2026

Staybridge Suites Winter Haven Auburndale by IHG
See all 38,896 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

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

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$49
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Ladies Luncheon Pontoon Tour

Ladies Luncheon Pontoon Tour (Gentleman welcome)

S$127
per adult
Ladies Luncheon Pontoon Tour (Gentleman welcome)
See all activities in Winter Haven

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* 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.