Hi Jenny,
Thanks for stopping by planDisney with your question. Looking at your plans, it sounds like you'll have a magical vacation wherever you choose to stay. Traveling with a large group, whether family or friends, is a recipe for unforgettable moments and treasured memories.
If I had to choose between the two options, I would pick three rooms at Disney's Contemporary Resort. Old Key West is fantastic, and with two larger suites you would have the advantage of space and kitchens to be able to prepare simple meals. However, looking at the parks you are planning to visit,
Disney's Contemporary Resort is going to put you closer to the fun and give you more options when it comes to dining.
You can't beat transportation from the Contemporary to Magic Kingdom. It's a relatively short walk, which is amazing, especially when guests are lining up to wait for the monorail or buses after watching
Disney Enchantment. You'll be in dreamland before most guests even get to the front of the line for the ride back to their resort. Hopping on the monorail to EPCOT is easy as well. The only park you'll be visiting that would require taking a bus is Disney's Animal Kingdom, and that's the only way to get to that park from any resort.
Spending a day
feature pool and water play area at Disney's Contemporary Resort is a fantastic way to rest from the parks. There's also a quiet pool nearby at Bay Lake Towers if some of the adults want a quieter experience. You can even enjoy a campfire and movies under the stars. Also, on your swim day, don't forget to head to
Disney Springs for some shopping, dining, and just plain fun. We love shopping for that perfect souvenir in
World of Disney and grabbing a delicious treat at
Amorette's Patisserie,
Gideon's Bakehouse, or
Everglazed Donuts.
Speaking of food. Staying at Disney's Contemporary Resort gives you so many nearby table service dining options. In your own resort you have
Chef Mickey's,
California Grill, and
Steakhouse 71, but restaurants at Disney's Polynesian Resort and Grand Floridian Resort are just a short monorail ride away. Plus, it's easy to hop on a boat to Disney's Wilderness Lodge for a meal at
Whispering Canyon Cafe (my kids' favorite) or
Story Book Dining with Snow White at Artist Point.
Hope this helps. Have a magical vacation!
Diane