We present $H$-band observations of $beta$ Pic with the Gemini Planet Imagers (GPIs) polarimetry mode that reveal the debris disk between ~0.3 (~6 AU) and ~1.7 (~33 AU), while simultaneously detecting $beta$ Pic $b$. The polarized disk image was fit with a dust density model combined with a Henyey-Greenstein scattering phase function. The best fit model indicates a disk inclined to the line of sight ($phi=85.27{deg}^{+0.26}_{-0.19}$) with a position angle $theta_{PA}=30.35{deg}^{+0.29}_{-0.28}$ (slightly offset from the main outer disk, $theta_{PA}approx29{deg}$), that extends from an inner disk radius of $23.6^{+0.9}_{-0.6}$ AU to well outside GPIs field of view. In addition, we present an updated orbit for $beta$ Pic $b$ based on new astrometric measurements taken in GPIs spectroscopic mode spanning 14 months. The planet has a semi-major axis of $a=9.2^{+1.5}_{-0.4}$AU, with an eccentricity $eleq 0.26$. The position angle of the ascending node is $Omega=31.75{deg}pm0.15$, offset from both the outer main disk and the inner disk seen in the GPI image. The orbital fit constrains the stellar mass of $beta$ Pic to $1.60pm0.05 M_{odot}$. Dynamical sculpting by $beta$ Pic $b$ cannot easily account for the following three aspects of the inferred disk properties: 1) the modeled inner radius of the disk is farther out than expected if caused by $beta$ Pic b; 2) the mutual inclination of the inner disk and $beta$ Pic $b$ is $4{deg}$, when it is expected to be closer to zero; and 3) the aspect ratio of the disk ($h_0 = 0.137^{+0.005}_{-0.006}$) is larger than expected from interactions with $beta$ Pic $b$ or self-stirring by the disks parent bodies.