Hey there @Proper15073 - thanks for your topic! Check out our Company Admin Guide - it’ll be helpful as you learn your way around!
Because Calendly sees each account as an individual user, it will not allow overlapping Calendly events in an effort to prevent double bookings. In order for all five housekeepers to be able to be booked simultaneously (meaning the overlap in event types you are looking for), they will each have to have a paid seat and separate Calendly account. You can create free email addresses for this purpose (even if you do not plan to actually give the logins to the housekeepers). At this time there is no workaround that will allow for double-booking in a single Calendly account. The Standard and Teams plans are designed for use cases like yours - multiple people within a single organization that need to be able to take bookings at the same time without an overlap issue. You can read more about our plans, pricing and features on our Pricing Page! Note: an annual subscription will result in a 20% discount for all paid plans!
We have plenty of resources for you to learn about creating a team and setting up team events! The first step is adding your desired team members to your account from your Admin Management page. Then, you can set up a team page. Your team page will have all of your events specific to that team: round robin or collective.
Round Robin events will allow your invitees to book an appointment at any time at least one assigned team member is available. Collective events allow invitees to book an appointment when all assigned team members are available. You can also use both Round Robin and Collective ETs on a team page as “one-on-one” event types since those event types cannot technically be created on a team page. Read more about that here.
If you'd like a more thorough breakdown of the team features, check out this recording that walks through the basics of using Calendly with your team.
I know this isn't exactly what you wanted to hear but do hope the information helps, at least somewhat!
