If your first thoughts of Florida tend to be spring break beach vibes in the hustle and bustle of Miami or major park destinations like Disney World, you might be surprised by what you find on this list. Florida is also home to some of the most charming small towns in North America, much in thanks to its history of European settlers blended with the local natural beauty. The best small towns in Florida tend to have that in common, a storied past that evoke a unique southern charm making them all worth visiting.
Whether you want to relax and unwind, take in a bit of history, or explore a potential move to these destinations, HomeExchange is a great way to visit the best small towns in Florida. Find out more about how it works today and discover our favorite small town Florida destinations.
Discover how HomeExchange works1. Mount Dora
Mount Dora is located on Florida's Central Coast, and has just the sort of warm local welcoming vibe you would expect from the best small towns in Florida. Mount Dora's originated as a popular destination for steamboat travel during the late 19th and early 20th centuries. Lake Dora, which the town overlooks, served as a hub for steamboat transportation, allowing residents and visitors to traverse the region's interconnected waterways. This historical significance is still celebrated today, with scenic boat tours offered on Lake Dora. The town's Victorian architecture and oak lined roadways also add to its charm and help make it our top pick for our favorite Florida small towns.
See homes in Mount Dora2. St. Augustine
It is no wonder St. Augustine made this list, and while though it's a "small town" the secret about this extraordinary place is out, drawing visitors from all over the US and even the world. It's actually the oldest continuously inhabited European settlement in the United States. Walking through the cobblestone streets of the historic district, you'll see centuries-old buildings, impressive fortifications, and iconic landmarks that tell the stories of its Spanish colonial past. The magnificent Castillo de San Marcos, a well-preserved 17th-century fortress, stands as a testament to the town's strategic importance and is a must-visit for history buffs. The local vibe in St. Augustine is a blend of laid-back coastal lifestyle and a deep appreciation for the town's cultural heritage.
See homes in St. Augustine3. Deland
Lesser known than places like St. Augusine, Deland is a well kept secret the list of the best small towns in Florida. It boasts a lot of history in its own right. In the early 20th century, DeLand became a hub for aviation pioneers, with the establishment of the DeLand Naval Air Station and the DeLand Municipal Airport. Notably, the town served as the training ground for the famous World War II fighter pilots. But nowhere is its history more evident than in its downtown. Deland has the sort of charming main street America vibes you would expect from great small towns. The MainStreet DeLand Association actively promotes local businesses and organizes festivals and events that bring the community together, fostering a lively and inclusive vibe. Wandering through the downtown area, visitors are greeted by an array of unique boutiques, antique shops, and art galleries that showcase the town's creative spirit.
See homes in Deland4. Matlacha
We couldn't forget Matlacha on our list of the best small towns in Florida. This colorful destination can't be missed on the Gulf Coast. Matlacha's local vibe can be described as bohemian, eclectic, and laid-back. As you cross the iconic Matlacha Bridge, you'll be greeted by a kaleidoscope of brightly painted buildings, art galleries, and quaint shops that line the streets. The town's artistic spirit is palpable, with local artists showcasing their creations in studios and galleries. The diverse art scene gives Matlacha a distinct personality, attracting art lovers or anyone seeking inspiration. Matlacha is also known for its connection to the Calusa Native American tribe, who were the original inhabitants of the region. The Calusa left behind fascinating artifacts and shell mounds, which offer a glimpse into the town's ancient history.
See homes in Matlacha5. Fernandina Beach
Nestled on Amelia Island's northeastern coast, you'll find one of the best small towns in Florida, Fernandina Beach. During the 19th century, the town thrived as a major shipping and trading hub, attracting merchants and entrepreneurs from around the world. This heritage is still visible today in the town's well-preserved historic buildings and waterfront area. The town's historic district is lined with beautiful Victorian-era homes and oak-lined streets and sets the stage for a stroll back in time. The local beaches or beautiful, as one would expect from the best small towns in Florida, and make the perfect setting for an array of local festivals that keep this small town alive today like the Eight Flags Shrimp Festival and Amelia Island Chamber Music Festival.
See homes in Fernandina Beach6. Anna Maria
The lovely town of Anna Maria is found on the barrier island of the same name. It's a truly tranquil coastal escape with white sand beaches and turquoise waters, but its tight knit community and great local vibe are what make it one of the best small towns in Florida too. Historically a fishing village, the town's unhurried pace and friendly atmosphere create a sense of belonging, making it easy to embrace the coastal lifestyle. After you hit the island's beaches, in the town you can explore a mix of locally-owned shops, restaurants with an emphasis on fresh seafood, and art galleries featuring local artists. Watching the colorful fishing boats go by is also a great local past time.
See homes in Anna Maria7. Safety Harbor
You'll find Safety Harbor along the shores of Tampa Bay, but its small town vibes are much calmer than the neighborhing hustle and bustle of Tampa itself. Here everything is laid back and tranquil. The locals roads dripping in Spanish Moss give an immediate sense of southern serenity. It's known for its local culture and health and well-being, beginning with the surrounding nature areas that local appreciate. The area has ancient roots as a sacred site for indigenous peoples. The Tocobaga Native American tribe considered the area's natural springs to be a place of healing and spiritual significance. This tradition of wellness continues to thrive in Safety Harbor, and the town is home to the renowned Safety Harbor Resort and Spa, where visitors can indulge in therapeutic treatments and experience the rejuvenating powers of the natural mineral springs.
See homes in Safety Harbor8. Dunedin
Dunedin is an unexpected twist on our list of the best small towns in Florida. Despite the initial impression along the Florida Gulf Coast, there is intriguing aspect of Dunedin's history that lies in its Scottish heritage. The town's name, Dunedin, means "Edinburgh" in Scottish Gaelic, paying homage to the Scottish settlers who founded the town in the 19th century. This heritage is celebrated each year during the Highland Games and Festival, where bagpipes, kilts, and traditional Scottish games take center stage. Dunedin's Scottish influence can also be seen in its architecture and street names, adding a unique cultural flavor to the town. This European heritage lends the town a distinct charm making it unique among the best small towns in Florida and keeps it lively and animated while all the while quaint today.
See homes in Dunedin9. Stuart
This small town gem is fittingly located on Florida's "Treasure Coast". Like most of the best small town in Florida, Stuart has historical heritage that give it charm. Stuart's history lies in its deep-rooted connection to the St. Lucie River and the Indian River Lagoon. The river served as a lifeline for the early settlers, providing transportation and sustenance. Its historic downtown area was built around the river, and its waterfront location continues to be a focal point for recreational activities and community gatherings. The Stuart Heritage Museum is a great place to get into the town's history, showcasing artifacts and exhibits that highlight its maritime heritage and the impact of early pioneers. Like all great small towns, its central area has great dining, galleries, and shops that make it welcoming and lively which is why he couldn't resist including it on this list.
See homes in Stuart10. Winter Park
Winter Park got it's not when it became a popular destination for wealthy vacationers in the winter months in the 19th century. Its sophisticated origins are still apparent today making it a very elegant pick for the best small towns in Florida. Its beautiful streets are lined with majestics oaks and dripping in Spanish moss. You can enjoy its timeless beauty as you stroll the downtown area that is still alive and well with bustling businesses. The town's founders envisioned a haven of beauty and tranquility, and they meticulously planned the city's layout with an emphasis on preserving green spaces and architectural integrity. This foresight is evident in Winter Park's iconic Rollins College, one of the oldest institutions of higher learning in Florida. The college's Mediterranean Revival architecture and lush campus blend seamlessly with the surrounding natural beauty, creating a harmonious atmosphere.
See homes in Winter ParkStay in The Best Small Towns in Florida with HomeExchange
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