Cant help too much as I only vacation in treasure island and Madera beach, About the only advice I can give though is if you are looking for a tolerant beach you could try the southern tip of treasure island at sunset beach, There used to be a 'gay' bar where the beach pavilion is now down by the mansions condos and public parking, and whilst the bar is now gone the beach is still home (and growing) to the LGB and occasionally the T community. Sunday afternoon it will be packed with "well groomed" men but other fringe groups can sometimes be seen further along the beach towards the mansions and lands end condos.
Whilst I cant confirm from a personal experience of being trans on the beach (I'm still questioning and pre everything and vacation male ;-( I have defiantly seen a couple of fellow girls and who knows how many not so obvious ones and never seen any negative reactions. Although I will admit I may look up from my book with jealous eyes if I notice you :-)
