| Winter Garden to Oakleaf Plantation (Florida) | 113.30 mi (182.34 km) |
| Winter Garden to Oakley (California) | 2,386.75 mi (3,841.11 km) |
| Winter Garden to Oakton (Virginia) | 756.04 mi (1,216.72 km) |
| Winter Garden to Oakville (Missouri) | 848.21 mi (1,365.06 km) |
| Winter Garden to Oatfield (Oregon) | 2,509.50 mi (4,038.65 km) |
| Winter Garden to Ocala (Florida) | 55.28 mi (88.96 km) |
| Winter Garden to Ocean Acres (New Jersey) | 878.96 mi (1,414.54 km) |
| Winter Garden to Ocean City (New Jersey) | 841.99 mi (1,355.04 km) |
| Winter Garden to Ocean Pines (Maryland) | 774.48 mi (1,246.41 km) |
| Winter Garden to Ocean Pointe (Hawaii) | 4,736.45 mi (7,622.59 km) |
| Winter Garden to Ocean Springs (Mississippi) | 451.16 mi (726.07 km) |
| Winter Garden to Oceanside (California) | 2,131.76 mi (3,430.74 km) |
| Winter Garden to Oceanside (New York) | 949.18 mi (1,527.55 km) |
| Winter Garden to Ocoee (Florida) | 4.64 mi (7.47 km) |
| Winter Garden to Oconomowoc (Wisconsin) | 1,076.53 mi (1,732.50 km) |
