Cedar Key is home to a lot of artists, writers, and nature lovers. It is very low key. Golf carts are street legal (there's no golf course, folks just like to drive them). It's a very pet friendly town. It is low density, there are no tall buildings. You can get a sense of what the town is like by visiting http://www.cedarkeyblog.com, it has local news and items of interest.
I second the vote for Anna Maria Island. I am a Florida native and have lived everywhere from Longboat Key to Port Charlotte. I think you would fit in well on Anna Maria Island it's very laid back and casual.
Wow - that's a tough one - in Pinellas County Gulfport is funky and artist influence - it's on the bay even though they have a "beach" - Ozona is a fish town tucked away where the mode of transportation is a golf cart and Molley Goodheads is a great hang out. My broker actually played at Woodstock and still plays at local beach bars. We used to love the keys and I hope they've held on to some of their casual charm. Someone said Ft Desoto off Tierra Verde - it's gorgeous but not much down their but condos and townhomes and multimillion dollar homes - somehow I think Woodstock is not the image that comes to mind. Good Luck - if you find it - move their fast - Old Fashion Florida is disappearing faster than you can say "Woodstock"
If you want a true hippie town, there is an neighbourhood of New Orleans called the Faurburg Marigny...it is just East of the French Quarter...sits on the edge of the quarter with many thespian type hippies. There are some really good values here, and this area did not flood after Katrina.
New Orleans is a haven for hippie types...with out the sanitized fluff of Florida...where Starbucks is in the category of McDonalds coffee...here in these parts of New Orleans a hippie is home...free music and free spirits...both real, in a glass and imagined.
New Smyrna Beach has a quaint, laid back, surfer town feel. It's just south of the Daytona Beach area, but doesn't have the touristy feel. They frequently close off some of the beachside streets and have special events for locals to enjoy.
The obvious answer is Anna Maria Island, north of Bradenton and Holmes Beaches. Very old Florida and more affordable during this year's correction. Great location close to the arts communities in Sarasota, Bradenton, St. Petersburg and Tampa.
If you want a place that is laid-back and not expensive on the coast of Florida you need to take a look at Flagler Beach Florida. I call it Mayberry Beach ... ha ha .... it a great little beach town that offers a wonderful beach living, and yet close to Jacksonville or Orlando ... about an hour either way. Check for Info on my web site ...
Cedar Key is very nice and affordable, however they pretty much close the sidewalks about 9:00 unless it's peak season. So I would have to say of course Key West or even Siesta Key but if your looking for a fun town it's definately in the lower Keys.
Siesta Key is great. But, like Diane stated, it's becoming a bit more high end. Woodstock on the coast is difficult to find. But, I would have to suggest Key West, or the "keys" leading down to Key West. Lastly, Fort Desoto National Park, in St. Petersburg, offers great camping sites and beaches.
Siesta Key, a part of Sarasota is a fabulous town. Becoming a bit more high end lately, but there are still some great beach cottages, a funky down-town with open air bars and nightly local entertainment, and one of the best laid back atmospheres you'll come across. Not to mention being one of the top 10 beaches in FL.
I grew up in south Florida, yet now live in Gainesville. I have two suggestions. First would be the Florida Keys. If you want something "smaller" you may want to consider Cedar Key on the Gulf Coast. Others may offer more places along the Atlantic Coast. The only area that I know up on the Atlantic side would be Crescent Beach south of St. Augustine.