How strict are resorts about this? We will be staying at Old Key West, whose check-in time is 4:00, but I would prefer to arrive from 1:00-2:00. Thanks guys!
In my experience, it all depends on availability. If you aren't picky about a room and they aren't fully booked, you sometimes can check in early. I've been able to check in by that time. If you have a particularly room request and/or the resort is very busy, you may have to wait until your room is ready.
You can check in anytime on your arrival day. If your room isn't ready, you can leave your bags with bell services. You'll get a text when the room is ready.