When I picked up the car at MCO and asked about the drop off, the agent said to get there before closing hours of 5 pm. So that's what we did and had the Hertz agent close out the contract on the spot. We were also told we could leave the vehicle and keys with the resort's valet, but they would not provide any kind of receipt. My guess is that 9 times out of 10 this would work just fine, but since we could make the deadline with no major inconvenience, we did so.
For the record, I had to do an after hours drop off at the Dayton, OH airport a couple of months ago, not knowing the location would be closed when I got there. It was around 7 pm and the Hertz kiosk in the airport garage was completely closed and vacant, so I filled out the return information and took a photo of it, along with noting the time, fuel, etc. and dropped the form and keys in the lockbox. Luckily, within a couple of days the contract was closed out and I received the email receipt for exactly what I expected.