When I cruise out of PC I rent a car from Budget. It's an easy drive out to the port and you don't have to pay mileage, then the Budget people shuttle you to the pier. I do the reverse on the return to MCO.
I always stay at the Best Western, there is a Publix grocery store right across the street for last minute items.
There are several hotels in the area, I've had several friends stay at the Radisson and really enjoyed it.
I don't think there is any good time to book air. I recently delayed booking air from Tulsa to Miami for our January cruise and the overnight delay cost me an additional $125 per ticket.....
Festival 5/1983, Festivale 6/1984, Holiday 7/2001, Inspiration 2/2002
Paradise 3/2004, Pride 9/2004, Victory 5/2005, Conquest 4/2006
Conquest 9/2006, Freedom 3/2007, Glory 9/2007, Conquest 2/2008
Valor 5/2008, Glory 8/2008 & 9/2008, Fantasy 2/2009
Conquest 9/2009, Dream 12/2009, Conquest 2/2010, Ecstasy 4/2010
Conquest 9/2010, Ecstasy 2/2011, Glory 2/2011, Conquest 10/2011
Triumph 11/2011, Magic 3/2012