I think most everybody allows parking in their lots "after hours", however with the new gravel lot we have not found parking a big deal anymore.
Yeah it is a short walk, but a very short walk.
Sometimes a short walk is good after being downtown having fun.

As for the coming and going when traveling in a group: In the past our villa greeters have loaded the luggage in their car and then wait for the rental car transaction. We head to the villa together.

On the way home, the ladies get driven into town and have Bloody Mary(s). The guys do the final villa walk around load up the car with luggage and return to town.

Smiling ladies at JJs (Now Cruz Bay Landing) watch the luggage, while rental car gets returned. Then it is ferry time.

Yeah it is a lot of moving parts, but hey no big deal your in the islands.

“Every time I open a bottle of wine, it is an amazing trip somewhere!” José Andrés