| Winter Garden to Orangeburg (South Carolina) | 344.77 mi (554.86 km) |
| Winter Garden to Orangevale (California) | 2,364.83 mi (3,805.83 km) |
| Winter Garden to Orchards (Washington) | 2,511.00 mi (4,041.06 km) |
| Winter Garden to Orcutt (California) | 2,309.02 mi (3,716.01 km) |
| Winter Garden to Oregon (Ohio) | 911.69 mi (1,467.23 km) |
| Winter Garden to Oregon (Wisconsin) | 1,084.41 mi (1,745.19 km) |
| Winter Garden to Oregon City (Oregon) | 2,508.30 mi (4,036.72 km) |
| Winter Garden to Orem (Utah) | 1,885.88 mi (3,035.03 km) |
| Winter Garden to Orinda (California) | 2,412.59 mi (3,882.69 km) |
| Winter Garden to Orland Park (Illinois) | 969.04 mi (1,559.52 km) |
| Winter Garden to Orlando (Florida) | 16.39 mi (26.38 km) |
| Winter Garden to Ormond Beach (Florida) | 60.24 mi (96.94 km) |
| Winter Garden to Oro Valley (Arizona) | 1,764.17 mi (2,839.16 km) |
| Winter Garden to Oroville (California) | 2,388.55 mi (3,844.00 km) |
| Winter Garden to Oshkosh (Wisconsin) | 1,136.70 mi (1,829.34 km) |
