| Winter Garden to Yonkers (New York) | 961.87 mi (1,547.98 km) |
| Winter Garden to Yorba Linda (California) | 2,157.97 mi (3,472.92 km) |
| Winter Garden to York (Pennsylvania) | 836.36 mi (1,345.99 km) |
| Winter Garden to Yorktown (Indiana) | 834.49 mi (1,342.98 km) |
| Winter Garden to Yorkville (Illinois) | 984.61 mi (1,584.57 km) |
| Winter Garden to Youngstown (Ohio) | 869.28 mi (1,398.96 km) |
| Winter Garden to Youngsville (Louisiana) | 635.43 mi (1,022.62 km) |
| Winter Garden to Ypsilanti (Michigan) | 953.47 mi (1,534.46 km) |
| Winter Garden to Yuba City (California) | 2,390.02 mi (3,846.36 km) |
| Winter Garden to Yucaipa (California) | 2,116.26 mi (3,405.79 km) |
| Winter Garden to Yucca Valley (California) | 2,080.79 mi (3,348.71 km) |
| Winter Garden to Yukon (Oklahoma) | 1,060.73 mi (1,707.07 km) |
| Winter Garden to Yulee (Florida) | 144.62 mi (232.74 km) |
| Winter Garden to Yuma (Arizona) | 1,972.34 mi (3,174.18 km) |
| Winter Garden to Zachary (Louisiana) | 592.90 mi (954.19 km) |
