Abstract: An umbrella and umbrella holder combination is provided comprising an umbrella having a canopy, a shaft connected to the canopy, and a handle connected to the shaft, the handle having a first connector portion; and an umbrella holder having a container adapted to receiving the handle, a second connector portion adapted to cooperate with the first connector portion when the handle is received in the container to prevent rotation of the handle relative to the container, and a clamp assembly adapted to connecting the umbrella holder to a frame member on a golf cart. The combination provides a directional locking fit between the umbrella handle and the umbrella holder so that the umbrella canopy cannot rotate relative to the golf cart, and this is advantageous especially when using an asymmetrical umbrella since the combination allows the umbrella canopy to being maintained in a desired orientation.