| Winter Garden to Seymour (Indiana) | 759.84 mi (1,222.85 km) |
| Winter Garden to Seymour (Tennessee) | 522.47 mi (840.84 km) |
| Winter Garden to Shady Hills (Florida) | 58.49 mi (94.12 km) |
| Winter Garden to Shafter (California) | 2,240.62 mi (3,605.94 km) |
| Winter Garden to Shaker Heights (Ohio) | 893.54 mi (1,438.01 km) |
| Winter Garden to Shakopee (Minnesota) | 1,297.38 mi (2,087.93 km) |
| Winter Garden to Sharon (Pennsylvania) | 879.10 mi (1,414.78 km) |
| Winter Garden to Sharonville (Ohio) | 759.27 mi (1,221.92 km) |
| Winter Garden to Shasta Lake (California) | 2,440.60 mi (3,927.77 km) |
| Winter Garden to Shawnee (Kansas) | 1,046.30 mi (1,683.86 km) |
| Winter Garden to Shawnee (Oklahoma) | 1,014.79 mi (1,633.15 km) |
| Winter Garden to Sheboygan (Wisconsin) | 1,103.65 mi (1,776.15 km) |
| Winter Garden to Shelby (North Carolina) | 466.27 mi (750.39 km) |
| Winter Garden to Shelbyville (Indiana) | 796.14 mi (1,281.26 km) |
| Winter Garden to Shelbyville (Kentucky) | 699.70 mi (1,126.07 km) |
