Florida’s ten prettiest, charming cities. Key West: High cost of living ($950,000 median home price, $3,100/month for a 2-bedroom rental), but boasts a vibrant, quirky atmosphere, strong sense of community, beautiful natural surroundings (coral reefs, mangroves), and a lower-than-average crime rate. Ideal for dreamers prioritizing lifestyle over affordability. Dunedin: More affordable than many coastal Florida towns ($430,000 median home price, $1,800/month rental), with a charming downtown, proximity to Honeymoon Island State Park, and a friendly, laid-back community. Lower crime rate than the US average. A great blend of small-town charm and coastal living. Gulfport: Affordable ($390,000 median home price, $1,750/month rental), artsy waterfront town with a strong local vibe, close proximity to St. Petersburg, and a crime rate 30% lower than the state average. Appeals to those who value creativity and community. Orlando: Surprisingly affordable for a major city ($410,000 median home price, $2,000/month rental), offering a diverse and dynamic atmosphere, numerous lakes150