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$160 per night from 5 Jul to 6 Jul
S$160
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Stay elsewhere! Housekeeping never came. Hotel smelled like weed. No microwave in room. Dailey per person charge for breakfast."

Reviewed on 22 Jun, 2026

Holiday Inn Winter Haven by IHG
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is S$281 per night from 5 Jul to 6 Jul
S$281
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (271 reviews)
"Great experience!!!"

Reviewed on 22 Jun, 2026

LEGOLAND Beach Retreat
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$173 per night from 29 Jun to 30 Jun
S$173
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (1,309 reviews)
"Love it"

Reviewed on 22 Jun, 2026

Best Western Plus Winter Haven Inn & Suites 
See all 37,992 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$50
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

S$141
per traveller
LEGOLAND Florida FasTrack Pass
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.