Florida Living

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 lakes and green spaces, and a booming job market. Safety varies by neighborhood, but many areas are safer than the city average. Excellent for families.
  • Bradenton: Relatively affordable coastal living ($390,000 median home price, $1,900/month rental) with a slower pace of life, proximity to Anna Maria Island, and a strong sense of community. Crime rate is average for Florida, but safer neighborhoods exist. Blends old Florida charm with modern amenities.
  • Tampa: Reasonably priced considering its growth ($440,000 median home price, $2,200/month rental), offering a balance of big-city energy and Florida charm, beautiful beaches nearby, and a diverse, welcoming community. Safety varies by neighborhood.
  • Naples: High cost of living ($620,000 median home price, $2,800/month rental), but offers luxurious coastal living, pristine beaches, an incredibly low crime rate, and a refined community atmosphere. A top choice for retirees seeking a high standard of living.
  • Venice: Surprisingly affordable for a coastal town ($450,000 median home price, $1,900/month rental), with old-world charm, beautiful beaches, a very safe environment (55% lower crime rate than national average), and a tight-knit community. Appeals to those seeking peaceful coastal living.
  • Stuart: Reasonably priced waterfront living ($470,000 median home price, $2,000/month rental) in a charming coastal town with a strong sense of community, a focus on outdoor activities, and a low crime rate (45% lower than the Florida state average).
  • Sarasota: Reasonably priced considering its amenities ($510,000 median home price, $2,300/month rental), offering breathtaking beaches, a vibrant arts and culture scene, a diverse and welcoming community, and a high quality of life. Crime rate 30% lower than national average.

Florida’s top ten locals’ vacation spots

• Ana Maria Island: A Gulf Coast gem with local laws limiting building heights and chain restaurants, preserving its Old Florida charm. Features small, locally-owned businesses, great beaches, and is easily explored by bicycle.
• Sanibel & Captiva Islands: Known for beautiful beaches, laid-back atmosphere, and opportunities for shelling (Sanibel is called the “Shelling Capital of the World”). Note: Still recovering from Hurricane Ian, many businesses remain temporarily closed.
• Destin: Offers some of Florida’s nicest beaches, rivaling those in the Caribbean. While featuring some tourist elements, it maintains a more relaxed vibe compared to nearby Panama City Beach. Home to Crab Island, a popular party spot.
• St. Augustine: The oldest continuously inhabited city in the US, rich in history and attractions like the Castillo de San Marcos, Flagler College, and Lightner Museum. Can be challenging to navigate by car due to limited parking.
• Delray Beach: Features an artsy downtown with galleries, restaurants, and the Morikami Museum and Japanese Gardens.
• Vero Beach: A laid-back area with a mix of culture, outdoor activities (kayaking, fishing, hiking), golf courses, and beautiful beaches. Home to the McKee Botanical Garden and Vero Beach Museum of Art.
• Islamorada & Key Largo: Popular Keys destinations offering water sports (snorkeling, scuba diving, kayaking), family-friendly attractions (Dolphin Research Center), and fishing (Islamorada is known as the “Sport Fishing Capital of the World”). Note: Beaches are smaller than those on the mainland.
• Cocoa Beach: Known for surfing (Kelly Slater’s hometown) and proximity to Cape Canaveral, offering opportunities to witness rocket launches.
• Flagler Beach: A quiet, old-Florida-style beach town with a laid-back atmosphere, great for relaxing, fishing, and enjoying natural scenery. Note: Fishing pier damaged by Hurricane Ian.
• St. Pete Beach & Pass-a-Grille Beach: Offers a laid-back, funky vibe, easy beach access, and a mix of old architecture and modern amenities. Close to the artsy downtown St. Petersburg.

Florida’s top places to reside.

• Sarasota (Rank 1): Offers a high-end beach town atmosphere, vibrant arts scene, family-friendly environment, top-rated schools, and some of the best beaches in the US (Siesta Key Beach). High cost of living (median home price: $535,000).
• Tampa (Rank 2): Large city with a mix of trendy neighborhoods, excellent restaurants, access to Tampa Bay and beaches (within a 30-40 minute drive). Booming job market, relatively affordable cost of living (median home price: $400,000), and a vibrant nightlife scene.
• Jacksonville (Rank 3): Florida’s largest city by land area, offering a blend of big-city amenities and affordable housing (median home price: $295,000). Access to beaches, numerous outdoor activities, and a milder climate than South Florida. Major employers in banking and healthcare.
• Cape Coral (Rank 4): Relaxed lifestyle with Gulf Coast beaches, golf courses, and over 400 miles of canals (more than any other city). Affordable compared to other areas, but cost of living is higher than the state average (median home price: $399,700). Popular retirement destination.
• St. Petersburg (Rank 5): Fast-growing city with affordable cost of living (6% below national average, median home price: $385,000), access to beautiful beaches, and a thriving downtown area. Strong arts and culture scene and diverse job opportunities.
• Orlando (Rank 6): Famous for theme parks (Disney, Universal, SeaWorld), but also offers a growing job market, diverse population, and relatively affordable housing (median home price: $360,000) compared to other Florida areas.
• Melbourne (Rank 7): Small-town feel with proximity to beaches and major attractions (Kennedy Space Center, Disney World). Abundant outdoor recreation opportunities and a diverse community (median home price: $332,500).
• Miami & Miami-Dade County (Rank 8): Vibrant and largest metropolitan area in the list, offering a diverse job market, cultural richness, and a lively nightlife scene. High cost of living and higher crime rates (median home price: $562,000). Tropical climate.
• Pensacola (Rank 9): Relaxed coastal lifestyle with beautiful beaches, abundant outdoor activities (fishing, parks), and a rich history (median home price: $285,000). Lower cost of living than the national average.
• Port St. Lucie (Rank 10): Quieter community with scenic waterways and golf courses, offering a more relaxed atmosphere and more affordable housing (though prices are rising) compared to other South Florida markets (median home price: $379,916).