| Winter Garden to Ridgefield Park (New Jersey) | 952.41 mi (1,532.76 km) |
| Winter Garden to Ridgeland (Mississippi) | 575.20 mi (925.70 km) |
| Winter Garden to Ridgewood (New Jersey) | 957.82 mi (1,541.46 km) |
| Winter Garden to Rifle (Colorado) | 1,671.63 mi (2,690.23 km) |
| Winter Garden to Rincon (Georgia) | 260.17 mi (418.71 km) |
| Winter Garden to Ringwood (New Jersey) | 961.41 mi (1,547.24 km) |
| Winter Garden to Río Grande (Puerto Rico) | 1,218.82 mi (1,961.50 km) |
| Winter Garden to Rio Grande City (Texas) | 1,065.57 mi (1,714.87 km) |
| Winter Garden to Rio Linda (California) | 2,376.69 mi (3,824.91 km) |
| Winter Garden to Rio Rancho (New Mexico) | 1,539.24 mi (2,477.17 km) |
| Winter Garden to Rio Rico (Arizona) | 1,764.90 mi (2,840.33 km) |
| Winter Garden to Ripon (California) | 2,354.91 mi (3,789.86 km) |
| Winter Garden to River Edge (New Jersey) | 956.33 mi (1,539.06 km) |
| Winter Garden to River Falls (Wisconsin) | 1,279.58 mi (2,059.29 km) |
| Winter Garden to River Forest (Illinois) | 986.47 mi (1,587.57 km) |
