The prediction of leaf wetness duration (LWD) is an issue of interest for disease prevention in coffee plantations, forests, and other crops. This study analyzed different LWD prediction approaches using machine learning and meteorological and temporal variables as the models’ input. The information was collected through meteorological stations placed in coffee plantations in six different regions of Costa Rica, and the leaf wetness duration was measured by sensors installed in the same regions. The best prediction models had a mean absolute error of around 60 min per day. Our results demonstrate that for LWD modeling, it is not convenient to aggregate records at a daily level. The model performance was better when the records were collected at intervals of 15 min instead of 30 min.