| Winter Garden to Hillcrest Heights (Maryland) | 759.25 mi (1,221.89 km) |
| Winter Garden to Hilliard (Ohio) | 799.05 mi (1,285.94 km) |
| Winter Garden to Hillsboro (Oregon) | 2,527.45 mi (4,067.54 km) |
| Winter Garden to Hillsborough (California) | 2,421.24 mi (3,896.61 km) |
| Winter Garden to Hillsborough (New Jersey) | 915.56 mi (1,473.44 km) |
| Winter Garden to Hilo (Hawaii) | 4,606.44 mi (7,413.34 km) |
| Winter Garden to Hilton Head Island (South Carolina) | 257.02 mi (413.63 km) |
| Winter Garden to Hinesville (Georgia) | 226.81 mi (365.02 km) |
| Winter Garden to Hinsdale (Illinois) | 982.64 mi (1,581.40 km) |
| Winter Garden to Hobart (Indiana) | 951.48 mi (1,531.26 km) |
| Winter Garden to Hobbs (New Mexico) | 1,311.65 mi (2,110.90 km) |
| Winter Garden to Hobe Sound (Florida) | 134.92 mi (217.13 km) |
| Winter Garden to Hoboken (New Jersey) | 945.62 mi (1,521.84 km) |
| Winter Garden to Hockessin (Delaware) | 846.61 mi (1,362.49 km) |
| Winter Garden to Hoffman Estates (Illinois) | 1,003.81 mi (1,615.48 km) |
