Yes, it's done all the time. Just reserve your DME ahead of time. They will want arrival times, so you can either just give them a 'dummy' flight arrival time, or tell them you haven't booked flights yet, but will be arriving on such and such a day...obviously the first day of your resort stay.
Then, that morning, get yourselves over to MCO, from wherever you are staying the previous night. Bring all your luggage with you....you will take it down to level 1 (ground transportation) with you and it will be put beneath the bus you are riding on. And yes, you should be prepared to tip the driver for this baggage service.
When you get to your resort, your bags will be unloaded and handed to you...this is when you would tip the driver. If your room isn't ready for you yet, you can have Luggage Assistence (Bell Services) store the bags for you until the room is ready.
Hope that helps.