Productive lets you add time off and vacation entitlements to a teammate. Each teammate can have their own number of days assigned.
This add-on has to be enabled first in Settings > Addons > Time Off Approval.
To add available days to their entitlement, go to Contacts > People and find the person in question.
Click on the Time off tab and select Add Entitlement:
First, select a time off category (learn how to configure them here), enter the total allocation and add a date range.
You can also add other time off categories when you click on New:
Hover over Information to see additional info:
Now, when a teammate request time off, it will show in their superior's Approvals page:
... under the Time off tab:
Every approved time off event will automatically be added to Scheduling: