I don't usually post on this board. But I have family from Anna Maria. It's a great place, beautiful beaches.
I don't have any condo recs since we always stayed with family.
We went to siesta key nearby last year around that time and the weather was beautiful. Perfect for the beach. We had a canopy that we used to keep my toddler out of the sun. That was nice. He even took a nap when we were on the beach.
We love the area! It's so quiet and friendly, with a lot of cute places to eat. There's not a whole lot to do (although you can take a side trip to Sarasota or Siesta Key), but if you are looking for a place to hang out on the beach, it's great.
We stay here when we go, but it might be a little tight for 5 adults. I liked the location, even though it's not right on the beach. I would definitely recommend the rental company though.
Anna Maria Island is so pretty! You can definitely go to Sarasota real easily and I would recommend going to Siesta Key because it is a real pretty beach. If you really want you can go to the Tampa area.