| Winter Garden to Rockport (Texas) | 941.60 mi (1,515.35 km) |
| Winter Garden to Rockville (Maryland) | 771.39 mi (1,241.43 km) |
| Winter Garden to Rockville Centre (New York) | 951.00 mi (1,530.48 km) |
| Winter Garden to Rockwall (Texas) | 930.78 mi (1,497.94 km) |
| Winter Garden to Rocky Mount (North Carolina) | 558.79 mi (899.28 km) |
| Winter Garden to Rocky Point (New York) | 986.20 mi (1,587.14 km) |
| Winter Garden to Rocky River (Ohio) | 893.36 mi (1,437.73 km) |
| Winter Garden to Roessleville (New York) | 1,070.44 mi (1,722.71 km) |
| Winter Garden to Rogers (Arkansas) | 906.84 mi (1,459.41 km) |
| Winter Garden to Rogers (Minnesota) | 1,323.75 mi (2,130.36 km) |
| Winter Garden to Rohnert Park (California) | 2,442.60 mi (3,930.98 km) |
| Winter Garden to Rolla (Missouri) | 874.69 mi (1,407.67 km) |
| Winter Garden to Rolling Meadows (Illinois) | 1,002.02 mi (1,612.60 km) |
| Winter Garden to Roma (Texas) | 1,076.24 mi (1,732.04 km) |
| Winter Garden to Rome (Georgia) | 448.49 mi (721.78 km) |
