We have done this many times. One trip, we did a last minute one when my parents were already there, we flew into TPA, because it was a lot cheaper. Drove to MCO and picked up my parents as they were walking outside. Our flights left about an hour apart from each other and if it worked out, great, if not, no biggie..they would have taken a cab to their townhouse (5 minutes from airport). When they landed we were hitting kissimee, so it was perfect timing, including picking up the rental car!!