On your departure day, be prepared for Bell Services to be VERY busy, and plan accordingly.
You certainly can get help from Bell Services to take your luggage from your room to the resort's main lobby, but there you must call and request this, and in addition there is nothing automatic, you'd still have to take this luggage YOURSELF to the Resort Airline Check-In desk or to the DME bus, whichever applies to you. If you need to take it to the bus, Bell Services can, of course, store it for you until you need it.
Now back to my original point .... Let me give you an example. Our DME bus was scheduled to pick us up at 4:00 p.m. from CBR. Checkout time is 11:00 a.m. So we planned on having our luggage stored while we went out to play for a few hours. At about 10:50 a.m., we called Bell Services to get our luggage and store it. They said they were too busy to come right now, but if we felt comfortable with it, we could leave all the luggage (including carry-ons) in one place inside the resort room near the door, and someone would get it eventually (they also suggested we leave a tip on one of the bags, if we wished). We followed this, and it worked perfectly. At about 3:40 p.m. we asked a Bell Services CM for our luggage out of storage -- the woman brought it to us on a cart, which we were allowed to keep until the luggage was loaded on the bus (we were early).
So what I'm trying to say in 10,000 words or less is, if you're in a rush, don't wait 'til the last minute to call Bell Services to pick up your bags on checkout day.