Hi Stephanie!
Thank you for visiting the Moms Panel!
If you are looking to share a room together, there is a very good guide to which Walt Disney World Resort hotels (in each of the categories - Value, Moderate and Deluxe) have rooms to accommodate five guests -
please see here for details. I would recommend having a look at which resort hotels appeal to you visually, and which suit your budget. All the Walt Disney World Resorts are wonderfully themed and have a variety of activities to enjoy. It may also help your decision if you know which theme park you would like to be closest to.
Once you have had a look at the resorts on the website, please come back and ask me any specific questions you may have, which may help you make your decision on where to stay.
All resort pools are open all year round, unless they are closed for maintenance work.