You've got the basic concepts already, but where you go the morning you check out varies depending on your resort -- you specifically want to visit the Resort Airline Check-In area. It should be easy to locate but it may not be the front desk is the point. For example, at Pop Century the RAC area is outside the main building. With an evening flight you would visit the RAC the morning you check out, not the night before. At the RAC area you can check in to your flight and check in your bags. The staff there will put airline tags onto your bags, although at the airport the airline may re-tag your bags with their own. With Southwest you probably want to check in online 24 hours in advance, if you have not purchased their automatic Early Bird Check In option. If you do check in online, in my experience you may receive SWA boarding passes at your room, which allows you to avoid the Southwest check-in area at the airport entirely, and go directly to security -- it's really nice to do that! For your carry ons, yes, you can check those bags with the luggage desk (typically right next to the RAC area) and pick them up again before you catch your Magical Express bus. Make sure to allow plenty of time for your carry ons to be retrieved prior to your designated Magical Express pick up time -- just in case; you don't want to panic while they go get your bags.