Hi Hillary,
Thank you so much for visiting the Disney Parks Moms Panel with your question. You are staying at one of my favorite Disney Vacation Club resorts. I love
Disney's Old Key West Resort. The overall feeling there is so relaxing, and it really puts me in a vacation state of mind. Since you are considering places to eat, do be sure to check out
Olivia's Cafe at Disney's Old Key West Resort. It is relaxing and the food is delicious, and I think it is one of the best kept secret restaurants at Walt Disney World.
I do like your plan to explore other resorts and their dining options. There are so many at Walt Disney World! Although they are geographically quite close to each other, you cannot walk from Disney's Old Key West Resort to the Disney's Port Orleans Resorts. You would need to take a bus or boat to a theme park or Disney Springs, and then from there switch to a bus or boat to the other resort. While this would work, it could be time consuming. Another option would be to take a cab. This would be an extra cost, but it should be fairly low as the distance is not too far. To get a cab, simply head to the lobby area of the resort. If there is not a cab waiting, ask a cast member and they can call one for you.
I hope that these thoughts are helpful for you, Hillary. Have a wonderful time planning your magical vacation, and please do let us know if you have any further questions.