Here we report the photophysical properties of three resorcinol derived cavitands. Steady-state absorption and fluorescence spectra for the three cavitands studied displayed absorption maxima ranging from 270nm to 290nm and emission maxima between 300nm and 320nm. The absorption/emission spectra are attributed to excitation of the substituted phenyl rings that constitute the cavitand cavity. The similarity of the absorption/emission spectra and fluorescence quantum yields between the cavitands and 5-hydroxy-1,3-benzenedicarboxylic acid (Hbdc), an analoguos substituted benzene, indicate weak intramolecular interactions between the monomers of the cavitand core. Fluorescence lifetimes were found to increase from ~4 ns to ~12 ns upon functionalization with groups with greater electron donating ability. Combined with polarization data, we find that the inclusion volume is related to the O•••H interactions at the upper rim of the cavitand.