Lots of things to consider in setting up a Cayman vacation.
Do you prefer to be "in the middle of everything" or "off in a relatively secluded area?"
Are you looking for a hotel, resort, or condo for accomodation? What level of comfort basic, moderate, or luxury?
Are you looking to do lots of shore diving, or hook up with a boat operator to take care of things?
In general, summer is considered off season for the island, however on East End summer can be very busy. If you want to boat dive on East End, then I'd suggest booking your dives pronto. We've been filling our boats and turning people away the last three weeks.
East End is the secluded part of the island. Seven Mile Beach/Georgetown/West Bay are on the heavily developed west side.
Most shore diving is on the west side though there are lots of boat operators to choose from. On East End there are only three dive operators to choose among and boat diving is the way to go. Only a couple of shore dives on East End.
Tons of housing choices all over the west side with everything from fairly basic to high end resorts. Many fewer options on East End with most tourists staying at one of two large resorts or at Cayman Dive Lodge (nice, but basic). There are a scattering of condos all over the island, and this is a popular option for families.