Fluorine-containing polymers have potential for use in medicine and other applications, but the synthesis of degradable fluorous polymers is underexplored. In this report, we present a facile route to degradable fluorinated polymers and characterize the effect of fluorous comonomer identity on the polymerization as well as the degradation kinetics of the resulting polymer. Copolymers of poly(ethylene glycol methyl ether methacrylate) (PEGMA), fluorous methacrylate (1H,1H,2H,2H-perfluorooctyl or 1H,1H,2H,2H,3H,3H-perfluoropentyl methacrylate), and cyclic ketene acetal 5,6-benzo-2-methylene-1,3-dioxepane (BMDO) were synthesized via ruthenium-catalyzed living radical polymerization. It was observed that increasing the fluorous monomer content led to enhanced BMDO incorporation in the resulting polymer. Density functional theory calculations suggest that this is due to the decreased energy gap between the singly occupied molecular orbital (SOMO) of the methacrylate radical and the highest occupied molecular orbital (HOMO) of BMDO. Moreover, polymers with higher fluorous monomer content were more hydrolytically stable, with a degradation rate constant 100-fold smaller for the polymer with highest fluorous content compared to the nonfluorous polymer. This work provides easy access to degradable fluorous polymers using vinyl monomers. In addition, the insights gained into modulation of reactivity of cyclic ketene acetals and polymer degradation will be useful in applying fluorous polymers for a variety of biomedical applications.