Hi Dana!
Thank you for bringing your question to the Disney Parks Moms Panel!
First, you are definitely not being silly! Traveling to
Walt Disney World is very magical, but also takes a lot of planning and as moms, we are always trying to make sure our kids are as comfortable as possible.
You know your kids best and you know their capability at walking around on their own. However, if it were me, I would suggest starting out just renting one. Since you will be there for so long, I feel like you will be able to relax throughout each day and not be in a "kamikaze" mode that someone would be trying to fit everything in in just two or three days. With a more laid-back approach to your daily plans, I think your kids could easily take turns riding in the double stroller. Having just one double stroller to deal with will also make your day go more smoothly.
If, once you're there you notice that you need a second stroller, you can always rent one while inside the parks from the
Walt Disney World Stroller Rental locations. I hope this helps! Please let me know if you have any other questions as you prepare for your vacation.
~Lori