Are there any places in Orlando to rent a double umbrella stroller...ones that offer drop off would be preferred. I didn't see any of those types of strollers when browsing the most popular stroller rental companies.
I don't think I've ever seen umbrella strollers for rent anywhere. The lightweight nature of umbrella strollers is probably what keeps them from being used as rentals, as they might not hold up well to the constant use as a rental.
I PURCHASED an umbrella stroller at the park - gift shop at the entrance to EPCOT, assume each park has by their rentals. It was about $30. You could bring handful of zip ties, buy two and connect them together. I'd bring sign or ribbon or something to mark it as yours.