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Two carboxylic functionalized poly(ionic liquids) and polyoxometalate ionic self-assemblies with tunable amphiphilic and oxidative activity and porous structure were designed and synthesized. They were used as efficient heterogeneous catalysts exhibiting excellent catalytic activity and quite stable reusability in additive−free Baeyer-Villiger oxidation of cyclic ketones, directly using 30% H₂O₂ solution in liquids−phase. Under optimum conditions, the corresponding lactones were obtained with yields ranging from 59.6 to 90.5%. The unique combination of carboxylic group with polyoxometalate anion, amphiphilic property, and porous structure is revealed to be responsible for their excellent catalytic performances in oxidation.