The modulation of the cloud point of aqueous poly(N,N-diethylacrylamide) solutions via the formation of supramolecular cyclodextrin complexes with hydrophobic end groups, namely adamantyl,tert-butyl phenyl and azobenzene, synthesized via RAFT polymerization is described. The dependence of the apparent cloud points after cyclodextrin complexation is investigated with respect to the type and quantity of the guest end group, the polymer chain length and the cyclodextrin/end group ratio. Furthermore, the effect is reversed via the addition of guest molecules or via biocompatible enzymatic degradation of the cyclodextrins entire.