This is a list of the largest metropolitan areas in the insular Caribbean , based on the latest official population estimates or projections.
| Rank | Metropolitan area | Population | Year | Country/territory |
|---|---|---|---|---|
| 1 | Santo Domingo | 4,751,036 [1] | 2025 | |
| 2 | Havana | 2,732,971 [2] | 2024 | |
| 3 | Port-au-Prince | 2,618,894 [3] | 2015 | |
| 4 | San Juan | 2,035,733 [a] [4] | 2023 | |
| 5 | Kingston | 1,190,763 [b] [6] | 2015 | |
| 6 | Santiago de los Caballeros | 1,074,684 [c] [8] | 2015 | |
| 7 | Nassau | 296,522 | 2024 | |
| 8 | Willemstad | 136,660 | ||
| 9 | Port of Spain | 81,142 | 2024 |