We have been going to Siesta Key Beach in Sarasota FL for many years. The beach itself is the best around, and it isn't just me saying that...they've won awards for their beach. It's not all that commercialized. There is parasailing, jet ski rental, bike rentals, and maybe even still the big trike looking thing with huge tires that you pedal in the water up closer to the beach but outside the swimming area. There are many restaurants in the area. The old Salty Dog is down in the village, along with the best place for breakfast, The Broken Egg (this is the one that Dick Vitale frequents when he's in town...he was even at the table beside us one time...signing his books. Now, it's true it can be hot and humid in summer, BUT, there is ALWAYS a gentle cooling breeze off the Gulf when you're out on the beach. True, we usually go in winter, but have been once or twice in summer. There is an Open Deck Daquiri bar or whatever that serves up grub when you're hungry. If the weather is nice, you can sit out on their covered deck and eat.
We almost always stayed at the Jamaica Royale condominiums on Midnight Pass Road. They have 1 and 2 bedroom garden apartments, along with the 2 tower buildings. Supposedly there is free wifi available there now, but I couldn't get it to work for me, but I'm not an expert at that type of thing.
Jamaica Royale has security guards on the premises. They have covered parking available too. For "entertainment" ther is the Marie Selby Botanical Gardens near by (very very nice, lots of photo ops), and there is Jungle Gardens close by also. If you want to take a day trip to Shell World on which would be on your way as you drive down to Sanibel Island, it's a pretty neat place to visit, especially your first time around (I bought a small lamp with clear glass base and filled it with all the shells I've collected from the beaches over the years). There is also the (sorry can't quite recall the exact name) Ringling Museum. It boasts lots of paintings and the best part, imho, was the miniature carnival display..which is not all "that" miniature. It's inside and I just adored it.
The ONLY reason we haven't stayed there the past 2 times we've been here is because I have a 6 yr old Shih Tzu named Molly, whom I refuse to leave behind for one or 2 months at a time. The Jamaica Royale will allow dogs IF you own the condo. It does have 3 heated pools (but the one up by the beach is always cold..it's in perpetual shade and there is always a strong breeze through there from the Gulf).
There are wonderful eateries in Sarasota itself, too. We love Mi Pueblo, out close to Palm Aire Country Club. And Sweet Tomatoes on Tamiami Trail is wonderful! And on Siesta Key in the village is a place run by brothers from New Jersey...a pizza place. It's sooo good...not quite sure of the spelling but it's something like Solanzaros Brothers. I'm sure I've butchered the spelling of their name though. They even have a place outside to eat and you can have your 4 legged baby with you
Love the pizza with pretty much everything including meatballs..omg they're to die for! I've been craving a New York (true authentic..NOT New York Style) pizza for ever so long, and this one comes very close. Hope this has helped you. Jamaica Royale is, or was the last time I checked, online for making reservations.