Hi Wendy

I alsways go to Siesta Key or Sarasota

Siesta key is more laid back and fun, lots of nice bars/restaurants. I stayed ina little apartment which is Banana Bay Club, they have studios up to 2 beds. Not on beach but different (only 5 minutes to beach)
Or go to the other end and stay at Best Western or tropical Breeze (1minute to beach)

Sarasota is very up market with Armands Circle with lots of boutiques and nice bars/restaurants

Hotel are more pricey - Holiday Inn on Lido Beach is not bad. Helmsley Sandcastle is a fun hotel and is on the beach - I love it there. I have been to Anna Maria Island and it is much more quiet.

Hope this helps

Oh yeah from Kissimmee it is about 1 hour 45 to 1 hour 55 depending on roadworks traffic etc.

Michele