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I rent out a private villa on HHI. Out of curiosity, I did a scan check of comparable units which advertise on vrbo.com and homeaway.com. What I discovered was that my rental fee was actually a couple hundred dollars lower compared to some others and I raised mine slightly this year to counter the increase in my costs.
I also scanned availability calendars to see if weeks were getting booked. Many units had their summer almost fully booked, some about half booked and others little to no booking.
I'm not sure about timeshares. We have rented a TS week to the same folks every year for the past 5 years and hopefully that will continue, but one never knows.