Climate change (CC) along with Land Use and Land Cover Change (LULCC) have a strong influence in water availability in already fragile Mediterranean ecosystems. In this work the Soil and Water Assessment Tool (SWAT) was implemented for the 2006–2018 period in a rainfed catchment of central Chile (36°) to test the hypothesis that adaptive plantation strategies could mitigate the impacts of climate change and increase streamflow. We also hypothesize that afforestation with exotic tree plantations will reduce water availability in Mediterranean catchments, acting in synergy with climate change. Five LULCC scenarios are analyzed: i) current long-term national Forest Policy (FP), ii) extreme scenario (EX) with large afforestation surfaces, both including the replacement of native shrublands with Pinus radiata; iii) adaptive plantation management scenario (FM), with lower planting density, iv) forced land displacement scenario (FLD), where plantations at the headwaters are moved to lowland areas and replaced with native shrublands, and v) pristine scenario (PR), with only native vegetation. Each LULCC scenario was run with present climate and with projections of different CMIP5 climate models under the RCP 8.5 scenario for the period 2037–2050, and then compared against simulations based on the present land cover and climate. Simulations with the five LULCC scenarios (FP, EX, FM, FLD and PR) with present climate resulted in variations of −2.5, −17.3, 0, 2.3 and 10.9% on mean annual streamflow (Q), while simulations with the current land cover and CC projections produced a 32.1% decrease in mean annual Q. The joint impact of CC and LULCC leads to changes in mean annual Q ranging from −46.2% (EX) to –23.3% (PR). Afforestation with exotic pines will intensify the reduction in water yield, while conservative scenarios focused on native forests protection and restoration could partially mitigate the effect of CC. We make a strong call to rethink current and future land management strategies to cope with lower water availability in a drier future.