So, is a full trip report in the future?
It's a fairly short story, really. I rented a relatively small unit in a double duplex but it was fine for me and my two dogs. Bonus was a huge screen porch that wasn't mentioned in the listing. The four units share a pool. It was only me and another couple in the other duplex, which basically meant I had the pool to myself all week. Plus nobody next door, which was nice.
Went to the beach, hung at the pool, visited Edison & Ford Winter Estates, and went kayaking (see above). That was basically the whole week. Had a disappointing restaurant experience the first night but made up for it the rest of the trip. I ate lunch every day at one of the two restaurants that were next door to my rental -- East End Deli and Lighthouse Cafe. There was also an ice cream joint next door so of course I had to hit that as well.
My favorite three things I ate were the aforementioned Cuban sandwiches at East End Deli, the Shrimp Ceviche Cocktail at Doc Fords, and the Salmon Oscar (salmon stuffed with crab meat) at Cips Place. Cips Place is a pretty nice joint but surprisingly allowed dogs on their patio, so my fur kids came with me that night. They behaved thank goodness.
Made my way to Captiva Island on the last evening there. Tried to go to Mucky Duck with my dogs, but the tables were full and the staff was less than helpful. The vibe kind of sucked anyway because it was a free-for-all for seating and there was a guy on the patio doing bad covers at about 100 decibels. We ended up at a place called RC Otters up the street that was much more chill. Ran into a couple from Winston-Salem there. Small world. Oh, and I swung by the Bubble Room on my way home to grab a piece of cake to go. That place is a trip!
ETA: Thanks again to you guys for the suggestion and the votes. Definitely a fun way to plan a vacation!