We present H and K band imaging polarimetry for the PDS 66 circumstellar disk obtained during the commissioning of the Gemini Planet Imager (GPI). Polarization images reveal a clear detection of the disk in to the 0.12 inner working angle (IWA) in H band, almost 3 times as close to the star as the previous HST observations with NICMOS and STIS (0.35 effective IWA). The centro-symmetric polarization vectors confirm that the bright inner disk detection is due to circumstellar scattered light. A more diffuse disk extends to a bright outer ring centered at 80 AU. We discuss several physical mechanisms capable of producing the observed ring + gap structure. GPI data confirm enhanced scattering on the East side of the disk which is inferred to be nearer to us. We also detect a lateral asymmetry in the South possibly due to shadowing from material within the inner working angle. This likely corresponds to a temporally variable azimuthal asymmetry observed in HST/STIS coronagraphic imaging.