| Winter Garden to Rowlett (Texas) | 937.00 mi (1,507.96 km) |
| Winter Garden to Roy (Utah) | 1,920.73 mi (3,091.12 km) |
| Winter Garden to Royal Kunia (Hawaii) | 4,734.13 mi (7,618.85 km) |
| Winter Garden to Royal Oak (Michigan) | 968.89 mi (1,559.28 km) |
| Winter Garden to Royal Palm Beach (Florida) | 152.29 mi (245.09 km) |
| Winter Garden to Royse City (Texas) | 925.14 mi (1,488.88 km) |
| Winter Garden to Ruskin (Florida) | 76.52 mi (123.15 km) |
| Winter Garden to Russellville (Alabama) | 547.63 mi (881.33 km) |
| Winter Garden to Russellville (Arkansas) | 820.46 mi (1,320.41 km) |
| Winter Garden to Ruston (Louisiana) | 711.99 mi (1,145.84 km) |
| Winter Garden to Rutherford (New Jersey) | 948.19 mi (1,525.96 km) |
| Winter Garden to Rutland (Vermont) | 1,145.32 mi (1,843.22 km) |
| Winter Garden to Sabana Grande (Puerto Rico) | 1,174.63 mi (1,890.38 km) |
| Winter Garden to Sachse (Texas) | 939.72 mi (1,512.33 km) |
| Winter Garden to Saco (Maine) | 1,206.02 mi (1,940.90 km) |
