Here's what I do every year for the weeks I want to rent (typically 2-3 weeks/year):
1- Demand Analysis: Figure out which weeks have been historically busy/will be busy in the year you're renting. Redweek has a heat map that shows busy times for a property per year. Use that as a starting point
2- Pricing Analysis: Figure out what your per night price should be. Again, use Redweek heat map, current listings, TUG listings etc and price somewhere in the middle of the range. I dont have a high profit motive for rentals.. generally looking for a little bit over MF
3- List as early as possible: (10-12 months out) on Redweek, TUG Marketplace, Local FB groups for families, Nextdoor etc
If you've followed these steps your until will rent no problem.
4- If your unit is not listed 6 months out, engage an agent and start looking at reducing the price by a $50/$100 every few weeks. When you update your listings, they also will show up on the top and help with discoverability. An agent will charge $350-500 per rental on contingency, so factor that into your pricing.
5- Worst case, you use the unit yourself or bank the points (depending on how far out you are from the reservation) to use the following year. I had to do this in early 2022 when Omicron hit. I refunded my rentals, minus admin fee, because it was the right thing to do. Thankfully, Vistana was understanding and let me rebook for later in the year.
Its also important to have a clear process for renting. When someone contacts me with interest, I send them a canned email I use for all outreach. It explains how the process works, how the renter can confirm the booking, costs charged directly to the renter during the stay etc. Renter then submits a non-refundable $250 deposit via Venmo/Zelle. Once the renter does that I get their name on the reservation and they are required to submit the rest of the payment and electronically sign a rental contract (modified version of Redweek rental contract) via a esignature tool. I send them a screenshot and ask them to remit payment and complete the contract. Once they do that, they get a confirmation and I tell them both the Vistana and Marriott confirmation #s.
At this point, most reasonable renters are satisfied and do not get back to me until the following year if they're looking to visit the same property again.
Screen renters who are not responsive, love drama, and keep wearing you down/asking for things last minute.
Once in a while some folks will continue to contact me with basic questions (answerable using Google but hey they'd rather lean on someone else than use their brain) or try to back out of the deal. Depending on the situation (aka Omicron), I do the best to help but if they are a nuisance, I choose not to deal with them the following year. You'll be surprised how often the "squeaky" renters will contact you after renting for the first time... probably looking for anyone who would put up with their BS.
After doing this a couple of years, you will know what to price your weeks for and how much you can increase every year. Good luck!