This review summarizes recent trends (2013–2023) in the synthesis and bioactivity of coumarin, coumarin–chalcone, and coumarin–triazole molecular hybrids. The synthesis of these compounds involves established reactions such as Pechmann condensation, Claisen–Schmidt condensation, and azide–alkyne cycloaddition, resulting in diverse structures with various substituents and fusion points. The synthesized compounds exhibit a wide range of bioactivities, including antioxidant, antimicrobial, anticancer, antidiabetic, and anti-cholinesterase activities. While some structure–activity relationship (SAR) studies have been reported, extensive SAR analysis is lacking. The mechanisms of action for these hybrids need further investigation to optimize their synergistic effects. The review highlights the potential of these molecular hybrids in medicinal chemistry and health science, aiming to provide valuable information for future research.This review summarizes recent trends (2013–2023) in the synthesis and bioactivity of coumarin, coumarin–chalcone, and coumarin–triazole molecular hybrids. The synthesis of these compounds involves established reactions such as Pechmann condensation, Claisen–Schmidt condensation, and azide–alkyne cycloaddition, resulting in diverse structures with various substituents and fusion points. The synthesized compounds exhibit a wide range of bioactivities, including antioxidant, antimicrobial, anticancer, antidiabetic, and anti-cholinesterase activities. While some structure–activity relationship (SAR) studies have been reported, extensive SAR analysis is lacking. The mechanisms of action for these hybrids need further investigation to optimize their synergistic effects. The review highlights the potential of these molecular hybrids in medicinal chemistry and health science, aiming to provide valuable information for future research.