I somehow still haven't met a single person who schedules their OoO replies correctly. They should start after your last day at the office before leave, and they should end after your last "presumed" day at the office before returning.
So, if you booked your leave from Monday, the automatic replies should start on Friday evening already. And, if you'll be back in the office on Monday, the replies should stop on Friday evening before that.
If a person writes you on Sunday before you come back, they don't need an auto reply, because they either do not expect you to read their message before Monday anyway, or they're a moron and thus do not matter :blobcattilt: