MD2 pineapple production in the Valle del Cauca Department, Colombia, has increased in recent years due to its preference in the national and international markets. Pineapple mealybug wilt (PMW), reported in all production areas around the world, is associated with two mealybug species, Dysmicoccus brevipes and D. neobrevipes, and a group of virus species known as pineapple mealybug wilt-associated viruses (PMWaVs). In a previous study, D. brevipes was determined to be the main mealybug species associated with pineapples in the region; hence, the objective of this study was to determine the occurrence and distribution of PMWaVs in pineapple plants and specimens of D. brevipes collected in five MD2 pineapple fields in the Department of Valle del Cauca. Our results confirmed the presence of three virus species in both plant and mealybug specimens. PMWaV3 showed the highest detection frequencies (92.6% and 88.7%), followed by PMWaV1 (26.5% and 8.3%) and PMWaV2 (12.0% and 2.0%) in plant and mealybug samples, respectively. Mixed infections of PMWaVs were found also in the studied plant material. The most common virus association consisting of PMWaV1 and PMWaV3 was found in 30 plant samples (20%). The correlation analysis between each virus species found in mealybugs and their pineapple host suggests that PMWaV3 is not only transmitted through infested plant material, but that D. brevipes may also play a role in the dynamics of disease dissemination. The results of this study contribute to the understanding of PMWaV transmission in MD2 pineapple-cultivated areas in the Valle del Cauca region.