| Winter Garden to Robbinsdale (Minnesota) | 1,307.90 mi (2,104.87 km) |
| Winter Garden to Robertsville (New Jersey) | 914.35 mi (1,471.50 km) |
| Winter Garden to Robinson (Texas) | 949.49 mi (1,528.06 km) |
| Winter Garden to Robstown (Texas) | 979.61 mi (1,576.54 km) |
| Winter Garden to Rochester (Michigan) | 980.98 mi (1,578.73 km) |
| Winter Garden to Rochester (Minnesota) | 1,226.40 mi (1,973.70 km) |
| Winter Garden to Rochester (New Hampshire) | 1,177.78 mi (1,895.46 km) |
| Winter Garden to Rochester (New York) | 1,034.51 mi (1,664.88 km) |
| Winter Garden to Rochester Hills (Michigan) | 979.64 mi (1,576.58 km) |
| Winter Garden to Rock Hill (South Carolina) | 443.43 mi (713.63 km) |
| Winter Garden to Rock Island (Illinois) | 1,026.44 mi (1,651.90 km) |
| Winter Garden to Rock Springs (Wyoming) | 1,792.09 mi (2,884.09 km) |
| Winter Garden to Rockford (Illinois) | 1,035.83 mi (1,667.01 km) |
| Winter Garden to Rockledge (Florida) | 54.50 mi (87.70 km) |
| Winter Garden to Rocklin (California) | 2,367.08 mi (3,809.44 km) |
