| Winter Haven to Yonkers (New York) | 997.83 mi (1,605.85 km) |
| Winter Haven to Yorba Linda (California) | 2,164.20 mi (3,482.95 km) |
| Winter Haven to York (Pennsylvania) | 873.18 mi (1,405.26 km) |
| Winter Haven to Yorktown (Indiana) | 868.51 mi (1,397.73 km) |
| Winter Haven to Yorkville (Illinois) | 1,016.62 mi (1,636.09 km) |
| Winter Haven to Youngstown (Ohio) | 906.23 mi (1,458.43 km) |
| Winter Haven to Youngsville (Louisiana) | 638.03 mi (1,026.82 km) |
| Winter Haven to Ypsilanti (Michigan) | 989.24 mi (1,592.02 km) |
| Winter Haven to Yuba City (California) | 2,402.10 mi (3,865.81 km) |
| Winter Haven to Yucaipa (California) | 2,122.68 mi (3,416.12 km) |
| Winter Haven to Yucca Valley (California) | 2,087.34 mi (3,359.24 km) |
| Winter Haven to Yukon (Oklahoma) | 1,074.74 mi (1,729.63 km) |
| Winter Haven to Yulee (Florida) | 181.42 mi (291.97 km) |
| Winter Haven to Yuma (Arizona) | 1,976.92 mi (3,181.55 km) |
| Winter Haven to Zachary (Louisiana) | 598.41 mi (963.05 km) |
