We just sold our final whole condo ownership on HHI, it was time

and miss it already. First pet-friendly one we owned was at Seascape where beejayohio will be staying (pets for owners only), second at Treetops/OceanBreeze right behind Seascape-- pet-friendly for owners *and* renters and guests. We spent many many weeks there off-season -- the few times we even went during high season were too intensely crowded, but our vacation rental at Treetops especially stayed rented almost all the time -- so mostly we'd grab the occasional last-minute vacancy and ride down for a week or 2. We never ran out of things to do, don't play golf either. I confess having our dog with us made it all the better, if you wanted to try out an off-season week, and even bring one or 2 dogs with you, just try a weekly rental. It's one of the most pet-friendly environments we've ever experienced, almost every single restaurant has pet-friendly seating outdoors which you'd have weather for almost all year, some covered in case of rain.
We got hooked when on the last day of one of our timeshare stays (Disney HHI) it was raining so we decided to inquire with a realtor, then came back down with our dog a few weeks later to go see one, staying at a motel, it was last-minute so we couldn't get a pet-sitter. We fell in love with the experience of having our dog with us, which was unplanned, and didn't look back for many years. Every day off-season we'd have a couple of beach walks, have a drink sitting on one of those boxes on the beach, photography and bird-watching at Pinckney Island (or off our balcony or patio), Fish Haul beach (one time we ran into a Road Scholar tour group there!), go to movies, Savannah, outlet shopping, thrift store and consignment shop browsing (there are over 100, some sell pretty nice artwork), and the restaurants are so close and varied and excellent, and many are still pretty inexpensive relatively. Also there's a wonderful annual lantern parade in Novenber, and we did an informative historic tour on HHI.