| The Villages to Oakleaf Plantation (Florida) | 87.93 mi (141.51 km) |
| The Villages to Oakley (California) | 2,354.41 mi (3,789.06 km) |
| The Villages to Oakton (Virginia) | 740.14 mi (1,191.13 km) |
| The Villages to Oakville (Missouri) | 814.25 mi (1,310.40 km) |
| The Villages to Oatfield (Oregon) | 2,475.35 mi (3,983.69 km) |
| The Villages to Ocala (Florida) | 21.36 mi (34.37 km) |
| The Villages to Ocean Acres (New Jersey) | 867.70 mi (1,396.43 km) |
| The Villages to Ocean City (New Jersey) | 830.83 mi (1,337.09 km) |
| The Villages to Ocean Pines (Maryland) | 763.61 mi (1,228.91 km) |
| The Villages to Ocean Pointe (Hawaii) | 4,707.63 mi (7,576.20 km) |
| The Villages to Ocean Springs (Mississippi) | 421.09 mi (677.68 km) |
| The Villages to Oceanside (California) | 2,101.60 mi (3,382.20 km) |
| The Villages to Oceanside (New York) | 937.80 mi (1,509.24 km) |
| The Villages to Ocoee (Florida) | 35.52 mi (57.17 km) |
| The Villages to Oconomowoc (Wisconsin) | 1,045.25 mi (1,682.16 km) |
