Esplanade on Marco is probably the closest to what you are looking for, and the Marina at Factory Bay is probably second, except neither have a pool for marina use. Both do have condos which have a pool, maybe you could befriend a local and use the pool as their guest. Esplanade is a little further from the Gulf, but there are probably 25 restaurants within walking distance, 4 or 5 nice ones on-site including Starbucks & Cold Stone Creamery and even a nice open air bar right next to the dock
. Winn-Dixie/McDonalds across the street and plenty of shops that will take your $$.
Esplanade is much more protected than Factory Bay.
Esplanade Marina marco Island Florida
The Marina at Factory Bay - Marco Island, Florida
I'm not sure if any of the Naples marinas have pools.