I, too, am a teacher and a family of 5, so I can absolutely relate to all of your questions! Our resort choices have often been determined by our budget, and there are a lot of choices for
rooms for 5 or more guests. In addition to the list provided in the above link,
Disney's Caribbean Beach Resort and
Disney's Port Orleans Resort - Riverside have some rooms for 5 guests. Just an fyi, the bed for the 5th guest is smaller, so it wouldn't work well for a larger child or young adult. Also, you can book two connecting rooms at any of the
Value Resorts which would also provide you with 2 bathrooms. I'd explore the above links to see which best fits your needs and budget. A reputable travel agent could also help you, or you could call Walt Disney World at (407) 939-5277 for price quotes. Both of these should be able to share with you any possible discounts, too.
We have done the
Disney Dining Plan and did save money. I really liked that I knew what our food budget would be and didn't have to worry about the price of the entrees my children would order. I did do
a lot of research beforehand to carefully chose our restaurants to make the most of our dollar. A lot of helpful information can be found at www.disneyfoodblog.com - click on
Disney Dining Plan at the top. You can also do an internet search for
Disney Dining Plan Pros and Cons to read further articles where costs are further analyzed.
Happy planning and please let us know if we can help further. -Kara