Twice, both at CSR.
For our honeymoon back in 2006, we had booked a standard king room. Imagine our surprise when, after many delays, we finally get our room assignment and open the door to find a giant suite!
In 2011, we were upgraded from a standard king to a preferred king in Casitas 1, which was much appreciated with a 6 month old. We were traveling with DH’s brother, sister-in-law, and 2 year old nephew that trip and had requested rooms close to each other. We arrived first (flying from different states) and when I checked in I asked if our rooms had been assigned near each other and after looking, the cm was like “nope, hang on, let me see what I can do” and we both ended up in Casitas 1. I have no idea where either room was originally assigned but neither of us had booked preferred so we both ended up with an upgrade.