Renting Car from Port then dropping off at airport?

[SkippyLaRue]

We are sailing with on Virgin 30 Nov - 6 Dec leaving Miami and finishing in San Juan.  We are staying in San Juan for a few days to visit.  However, we aren't flying out until 2:00am on the 9th.  We are trying to figure out our options as far as getting a car rental at the Port upon arrival on the 6th and dropping off at the airport around 11pm on the 8th.  Off site rentals are cheaper but then dealing with the return late might be an issue.  We thought about paying for 3 nights hotel instead of 2 nights so that we would have somewhere to stay until 11pm and maybe grab a couple hours of sleep before heading to the airport.  Otherwise we would be out of our hotel at 11am and be in our rental car until 11pm (or not rental if we had to return it earlier).  We won't get home until 2:30pm on the 9th so that will be a very long day.  Any suggestions?  Different options? rental recommendations? This is our first time staying somewhere after a cruise and want to make the most of our time.  This is my first post as well so thanks in advance 🐵