Hello and welcome to planDisney, Lauren!
Lauren, it is possible to book two rooms at a
Walt Disney World Resort Hotel online but you have to make two separate resort reservations. It is easiest to go ahead and give a Cast Member a call at (407) W-DISNEY and have them help you with your reservations. The call centers open up around 7:00 a.m. Mickey Mouse's time. The early you can call, the less waiting on hold you will have to do. I like to set my alarm for just before 7:00 a.m. and start calling to join the waiting queue.
Unfortunately, adjoining and connecting rooms are not a guarantee but you can have the Cast Member helping you make a note on your reservation requesting it. This is another reason that I prefer calling. Adjoining rooms are considered side by side or very near to each other and connecting rooms have a little door on the inside that you can pass through to go from room to room. Keep that in mind when making your request. While adjoining and connecting rooms are not a guarantee, I know firsthand just how hard Cast Members work to try to make room requests happen, especially if you have a large family. To better the chances for your room request, I suggest also calling the resort on the day of your check-in, just to remind them of the request. If they have it available, they will do their very best!
If you are looking at Walt Disney World Resort Hotels that sleep a lot of people, I would consider the family suites at
Disney's Art of Animation Resort, the family suites at
Disney's All-Star Music Resort,
The Cabins at Disney's Fort Wilderness Resort, or the multi-room suites at several of the deluxe villas. I've stayed in a number of these options with friends or extended family and have always enjoyed it.
I hope this helps point you in the right direction, Lauren. If you have any other questions while you are planning your trip to the most magical place on earth, please feel free to stop back by and
ask me. I'm happy to help!
Have a great day!