Hi Jennifer, and welcome back to the Disney Parks Moms Panel!
I am happy to answer your next question regarding your upcoming stay at Disney's Old Key West Resort. I can't wait until you are hearing those steel drums playing calypso beats, soaking up the beauty and serene qualities of this fabulous Resort!
I am happy to report that you should have no problem arranging a taxi or Uber to pick you up directly at your Villa. Be sure to provide your Uber driver with your building unit number. Once you see from the Uber mobile app on your phone that your driver is approaching your Villa, you will likely want to proceed outside so the driver will be able to find you. Your Uber driver should be prepared to provide photo identification upon request to Disney Security Cast Members located at the Front Gate of the Resort, which is standard practice when entering onto Disney Resort hotel properties.
On the topic of transportation, if you have a chance during your stay to visit to nearby
Disney Springs, where a mecca of dining, shopping and entertainment venues await, be sure to use the complimentary and relaxing Disney water transportation. For my family, the boat ride over is a pleasurable experience in and of itself.
Wishing you a Magical and enjoyable upcoming Disney Vacation!
Magically Yours,
Trish