| Winter Garden to Shelbyville (Tennessee) | 558.29 mi (898.48 km) |
| Winter Garden to Shelton (Connecticut) | 1,002.43 mi (1,613.26 km) |
| Winter Garden to Shelton (Washington) | 2,564.25 mi (4,126.77 km) |
| Winter Garden to Shenandoah (Louisiana) | 579.96 mi (933.36 km) |
| Winter Garden to Shepherdsville (Kentucky) | 693.73 mi (1,116.46 km) |
| Winter Garden to Sheridan (Wyoming) | 1,786.20 mi (2,874.61 km) |
| Winter Garden to Sherman (Texas) | 954.78 mi (1,536.58 km) |
| Winter Garden to Sherrelwood (Colorado) | 1,541.65 mi (2,481.04 km) |
| Winter Garden to Sherwood (Arkansas) | 760.01 mi (1,223.11 km) |
| Winter Garden to Sherwood (Oregon) | 2,520.41 mi (4,056.21 km) |
| Winter Garden to Shiloh (Illinois) | 840.53 mi (1,352.70 km) |
| Winter Garden to Shiloh (Ohio) | 793.26 mi (1,276.63 km) |
| Winter Garden to Shiloh (Pennsylvania) | 835.75 mi (1,345.01 km) |
| Winter Garden to Shirley (New York) | 979.68 mi (1,576.64 km) |
| Winter Garden to Shively (Kentucky) | 709.85 mi (1,142.39 km) |
