Hi, Tammi!
Let me start by stressing that free room upgrades are few and far between. Often times,
resorts are at or very near capacity with rooms being assigned several days before your arrival, so please do not count on an upgrade.
That said, it never hurts to ask. When arriving, you may ask the Cast Member "Are you completely booked for the duration of my stay?" then if not 100% booked, politely follow-up with "Would I be able to be upgraded to a pool view" or whatever the case may be. Please know that their ability to move rooms will need to be authorized, and just the calls alone take a while to reach the proper management. If an upgraded room is available, they might offer it to you OR they may give you a price to upgrade as it might not be complimentary. Be ready for many scenarios. Allow plenty of time, and most of all, be kind and patient!
Honestly, your best option is to book the exact room you desire. This way, you avoid the stress of asking for a possible upgrade, dealing with figuring out if you want to incur any additional expenses, and just overall peace knowing your perfect room is waiting for you. Room requests such as lower floor, near elevator, etc, can be made during the
online check-in process.
I hope that you find the perfect resort room for you and your family!
Cathy