| Winter Garden to Ramsey (New Jersey) | 961.71 mi (1,547.72 km) |
| Winter Garden to Rancho Cordova (California) | 2,365.85 mi (3,807.47 km) |
| Winter Garden to Rancho Cucamonga (California) | 2,146.28 mi (3,454.11 km) |
| Winter Garden to Rancho Mirage (California) | 2,080.79 mi (3,348.71 km) |
| Winter Garden to Rancho Palos Verdes (California) | 2,192.02 mi (3,527.71 km) |
| Winter Garden to Rancho San Diego (California) | 2,109.96 mi (3,395.65 km) |
| Winter Garden to Rancho Santa Margarita (California) | 2,148.15 mi (3,457.12 km) |
| Winter Garden to Randallstown (Maryland) | 796.80 mi (1,282.33 km) |
| Winter Garden to Rantoul (Illinois) | 893.76 mi (1,438.37 km) |
| Winter Garden to Rapid City (South Dakota) | 1,603.57 mi (2,580.70 km) |
| Winter Garden to Ravenna (Ohio) | 872.12 mi (1,403.55 km) |
| Winter Garden to Raymondville (Texas) | 1,000.97 mi (1,610.91 km) |
| Winter Garden to Raymore (Missouri) | 1,022.46 mi (1,645.49 km) |
| Winter Garden to Raytown (Missouri) | 1,031.26 mi (1,659.65 km) |
| Winter Garden to Reading (Ohio) | 755.66 mi (1,216.12 km) |
