Rentals and schedules

I posted this a couple days ago but may have posted in the wrong section, so I am posting here hoping to get some assistance.

I live in a resort timeshare area and I have started a business for renting beach items (Chairs, umbrellas, surfboards, etc.) I’m looking for some sort of plug in or program that will allow people to pay an annual membership fee and then they can have their own “dashboard” on my site and schedule a time to check out these items out and back in. As this is a timeshare area, it would be great if they could schedule times well in advance. I might do some sort of delivery service for said items if demand is there.