Hello there, Lauren!
Having your very own Mary Poppins to help watch your little Mouseketeers while you have a romantic meal sounds like a super idea! I’m not sure if you are set on your advanced dining reservation, but my family and I recently had wonderful dining experiences at the newly renovated
Narcoossee’s at Disney’s Grand Floridian Resort & Spa and
Topolino’s Terrace - Flavors of the Riviera at Disney’s Riviera Resort. If you eat early enough, you may even catch the fireworks at
Magic Kingdom Park or
EPCOT from the restaurant or their terraces.
Now, I spoke with a friendly Cast Member, and they shared that if your sister wants to watch your children at the pool, she will need to be a Walt Disney World Resort Guest since Resort amenities are reserved for Resort Guests. If she is a Resort Guest, she will just need to make sure she has a Magic Band or key card to the room, which should also let her into the pool.
I’m not sure what Resort you are staying at, but look out for signage around the Resort with details about “Recreation Experiences” available on the property. Usually, the Resorts have signs up that describe if they have poolside activities, movies under the stars, or even a campfire available. I always like to snap a photo of the sign so I can reference it during my trip. Besides some pool time, it may be fun for your sister to surprise your little ones with one of these fun activities.
May the magic be with you!Melanie