| Key West to Winder (Georgia) | 661.79 mi (1,065.04 km) |
| Key West to Windsor (California) | 2,576.08 mi (4,145.79 km) |
| Key West to Windsor (Colorado) | 1,729.82 mi (2,783.88 km) |
| Key West to Winfield (Kansas) | 1,253.72 mi (2,017.68 km) |
| Key West to Winnetka (Illinois) | 1,259.14 mi (2,026.39 km) |
| Key West to Winona (Minnesota) | 1,457.30 mi (2,345.30 km) |
| Key West to Winston-Salem (North Carolina) | 802.32 mi (1,291.22 km) |
| Key West to Winter Garden (Florida) | 275.07 mi (442.69 km) |
| Key West to Winter Gardens (California) | 2,194.48 mi (3,531.67 km) |
| Key West to Winter Haven (Florida) | 238.25 mi (383.43 km) |
| Key West to Winter Park (Florida) | 280.05 mi (450.70 km) |
| Key West to Winter Springs (Florida) | 286.70 mi (461.41 km) |
| Key West to Winterville (North Carolina) | 801.30 mi (1,289.56 km) |
| Key West to Winton (California) | 2,444.80 mi (3,934.52 km) |
| Key West to Wisconsin Rapids (Wisconsin) | 1,442.88 mi (2,322.09 km) |
