Hey Jaynee! Welcome back to the Disney Parks Moms Panel. It makes me so incredibly happy to help answer one of your questions! I love shopping around for a great deal. We always travel on a strict budget so I am always trying to find what offer will give my family the most bang for our buck!
Without actually knowing what special offers will be available for the dates you are hoping to travel, it will be pretty hard to figure out what will be a better deal. Typically there have been some
special offers during those travel dates; however it is important to also note that Labor Day is observed during your planned travel dates.
It has been my personal experience that the free dining discount seems to be comparable to room discounts. What I mean by that is usually when I price this out for my family looking at the two different offers, the price using either discount typically comes out to about the same no matter the discount. Please be aware though that special offers and discount amounts can and do change often and without any advanced notification.
My best piece of information to you would be to book the room/package that you want at
Disney's Caribbean Beach Resort. If one or both of these special offers eventually are announced, then I would suggest that you call the Walt Disney World Resort Reservation line and ask them to price both offers out. This way you will know what the best deal is! Once you figure out the best deal, based on availability, the Cast Member assisting you should be able to help modify your reservation!
I hope that you have a magical time!
~Heather~