| Winter Springs to Seymour (Indiana) | 756.51 mi (1,217.49 km) |
| Winter Springs to Seymour (Tennessee) | 517.64 mi (833.07 km) |
| Winter Springs to Shady Hills (Florida) | 79.93 mi (128.64 km) |
| Winter Springs to Shafter (California) | 2,255.19 mi (3,629.38 km) |
| Winter Springs to Shaker Heights (Ohio) | 883.53 mi (1,421.91 km) |
| Winter Springs to Shakopee (Minnesota) | 1,297.48 mi (2,088.10 km) |
| Winter Springs to Sharon (Pennsylvania) | 867.87 mi (1,396.70 km) |
| Winter Springs to Sharonville (Ohio) | 753.54 mi (1,212.70 km) |
| Winter Springs to Shasta Lake (California) | 2,452.37 mi (3,946.71 km) |
| Winter Springs to Shawnee (Kansas) | 1,052.51 mi (1,693.84 km) |
| Winter Springs to Shawnee (Oklahoma) | 1,026.52 mi (1,652.02 km) |
| Winter Springs to Sheboygan (Wisconsin) | 1,099.65 mi (1,769.72 km) |
| Winter Springs to Shelby (North Carolina) | 456.40 mi (734.51 km) |
| Winter Springs to Shelbyville (Indiana) | 792.25 mi (1,275.00 km) |
| Winter Springs to Shelbyville (Kentucky) | 695.89 mi (1,119.93 km) |
