A multicomponent reaction for the preparation of dioxaspirodecanes starting from allylsilyl alcohols was achieved. The one-pot sequence involves the sequential acid-catalyzed reaction of an allylsilyl alcohol with an aldehyde to afford an alkenediol. The subsequent Prins cyclization of the homoallylic alcohol moiety generates a tetrahydropyranyl carbocation which is intramolecularly trapped by the second hydroxyl group. The chemoselectivity of the process shows dependence on the nature of the aldehyde and the concentration of the catalyst.