Droughts constitute natural hazards that affect water supply for ecosystems and human livelihoods. In 2013–2016, the Caribbean experienced the worst drought since the 1950s, and climate projections for the southern Caribbean predict less rainfall by the end of the 21st century. We assessed streamflow response to drought for a watershed in the Colombian Caribbean by analyzing the effects of drought length and land cover on streamflow recovery. We generated a calibrated SWAT model and created annual and monthly drought scenarios from rainfall records. We used our model to predict water yield for selected land covers (wet forest, shade coffee, shrub, and dry forest) under drought conditions. Annual scenarios resulted in water yield reductions of ~15 mm month−1 (wet forest, coffee, and shrub) and 5 mm month−1 (dry forest) for the first month after a two-year drought. Maximum water yield reductions for monthly scenarios occurred after a 10-month drought and were ~100 mm month−1 (wet forest, coffee, and shrub) and 20 mm month−1 (dry forest). Streamflow recovered within nine months (annual scenarios), and two to eight months (monthly scenarios) after drought termination. Drought response seems to be conditioned by climatic factors (rainfall seasonality and spatial variability) and catchment properties.