Hi Ashley,
Thank you so much for visiting the Disney Parks Moms Panel with your question. Do not worry, your luggage can be handled for you on both your arrival and departure days, and it will be quite simple!
First, I am glad to hear that you are taking
Disney's Magical Express as your transportation to and from the airport. This will make having your luggage handled even simpler! Before you leave home, be sure to put the luggage tags that you receive from Disney's Magical Express on your luggage. When you arrive at Orlando International Airport, you do not even need to claim your luggage. It will be picked up by Disney and will magically appear in your room later that day. If you have any carry-on luggage when you arrive at your resort that you do not want to take with you to the theme parks, you can give this to Bell Services to store when you arrive at your resort.
On your check-out day, you have a couple of options. If you are flying with a participating airline, you can choose to use
Resort Airline Check-In Service. This service is amazing! From your resort, you can check into your flight, get your boarding passes, and check your luggage. Your luggage will be taken to the airport, and you will not have to handle it again until you arrive at your home airport. There is a list of participating airlines on the link that I provided. If you are not flying a participating airline, or if you choose not to use Resort Airline Check-In Service, you can leave your luggage with Bell Services when you check out of your room, and then claim it from them when you return to your resort to catch your motor coach back to the airport.
I hope this information is helpful for you, Ashley! Please do let us know if you have any further questions.