| Winter Garden to Reedley (California) | 2,257.57 mi (3,633.20 km) |
| Winter Garden to Reidsville (North Carolina) | 550.14 mi (885.37 km) |
| Winter Garden to Reisterstown (Maryland) | 801.89 mi (1,290.52 km) |
| Winter Garden to Rendon (Texas) | 970.22 mi (1,561.41 km) |
| Winter Garden to Reno (Nevada) | 2,298.18 mi (3,698.56 km) |
| Winter Garden to Renton (Washington) | 2,527.70 mi (4,067.94 km) |
| Winter Garden to Republic (Missouri) | 907.66 mi (1,460.73 km) |
| Winter Garden to Reston (Virginia) | 759.17 mi (1,221.77 km) |
| Winter Garden to Revere (Massachusetts) | 1,126.83 mi (1,813.45 km) |
| Winter Garden to Rexburg (Idaho) | 1,970.54 mi (3,171.27 km) |
| Winter Garden to Reynoldsburg (Ohio) | 791.75 mi (1,274.20 km) |
| Winter Garden to Rialto (California) | 2,136.12 mi (3,437.76 km) |
| Winter Garden to Richardson (Texas) | 946.98 mi (1,524.02 km) |
| Winter Garden to Richfield (Minnesota) | 1,297.91 mi (2,088.79 km) |
| Winter Garden to Richfield (Wisconsin) | 1,080.38 mi (1,738.71 km) |
