| Winter Garden to Rome (New York) | 1,069.80 mi (1,721.68 km) |
| Winter Garden to Romeoville (Illinois) | 975.51 mi (1,569.94 km) |
| Winter Garden to Romulus (Michigan) | 950.48 mi (1,529.66 km) |
| Winter Garden to Ronkonkoma (New York) | 973.24 mi (1,566.28 km) |
| Winter Garden to Roosevelt (New York) | 953.38 mi (1,534.31 km) |
| Winter Garden to Rosamond (California) | 2,183.93 mi (3,514.69 km) |
| Winter Garden to Rosaryville (Maryland) | 757.57 mi (1,219.18 km) |
| Winter Garden to Roscoe (Illinois) | 1,044.90 mi (1,681.61 km) |
| Winter Garden to Rose Hill (Virginia) | 753.17 mi (1,212.11 km) |
| Winter Garden to Roseburg (Oregon) | 2,515.92 mi (4,048.98 km) |
| Winter Garden to Rosedale (California) | 2,240.71 mi (3,606.08 km) |
| Winter Garden to Rosedale (Maryland) | 799.81 mi (1,287.17 km) |
| Winter Garden to Roselle (Illinois) | 997.30 mi (1,605.01 km) |
| Winter Garden to Roselle (New Jersey) | 934.15 mi (1,503.37 km) |
| Winter Garden to Roselle Park (New Jersey) | 934.75 mi (1,504.33 km) |
