| Winter Garden to Siloam Springs (Arkansas) | 919.84 mi (1,480.35 km) |
| Winter Garden to Silver Firs (Washington) | 2,533.47 mi (4,077.23 km) |
| Winter Garden to Silver Spring (Maryland) | 768.77 mi (1,237.21 km) |
| Winter Garden to Silver Springs Shores (Florida) | 46.85 mi (75.39 km) |
| Winter Garden to Silverdale (Washington) | 2,553.31 mi (4,109.16 km) |
| Winter Garden to Silverton (Oregon) | 2,512.00 mi (4,042.67 km) |
| Winter Garden to Simi Valley (California) | 2,213.87 mi (3,562.88 km) |
| Winter Garden to Simpsonville (South Carolina) | 429.21 mi (690.75 km) |
| Winter Garden to Sioux City (Iowa) | 1,269.50 mi (2,043.07 km) |
| Winter Garden to Sioux Falls (South Dakota) | 1,332.91 mi (2,145.11 km) |
| Winter Garden to Skokie (Illinois) | 993.91 mi (1,599.55 km) |
| Winter Garden to Sleepy Hollow (New York) | 970.61 mi (1,562.04 km) |
| Winter Garden to Slidell (Louisiana) | 507.12 mi (816.13 km) |
| Winter Garden to Smithfield (North Carolina) | 517.76 mi (833.26 km) |
| Winter Garden to Smithfield (Utah) | 1,924.01 mi (3,096.39 km) |
