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The fruit of Prunus avium L., commonly known as sweet cherry, is an excellent source of phytochemicals, namely, phenolic compounds. This study aims to determine in vitro the bioavailability and the bioactivity of phenolic compounds present in cherries. Caco-2 cells were used, and the permeability and integrity of the monolayer formed were investigated. After incubation, the phenolic compounds that permeabilized the cell monolayer were quantified using a high-performance liquid chromatography–diode array detector, and the antioxidant activity was evaluated by the 1,1-diphenyl-2-picrylhydrazyl method. The results demonstrated that the phenolic compounds of sweet cherries after undergoing a simulated digestion were absorbed by the cellular barrier, becoming bioavailable. Contrary to what was found after incubation with the in vitro digested extract, the integrity of the cell monolayer was altered and its permeability increased upon incubation with the sweet cherry phenolic extract. Regarding the antioxidant activity, it was verified that this decreased after the absorption by the cellular monolayer. This study suggests that digestion is an indispensable process for absorption because without it the phenolic content of the food matrix does not become bioaccessible.