Close your eyes and imagine a bustling main street, the trill of an ice cream truck, and the friendly smile of your neighbors. You’re probably thinking of your favorite small town. Every state in the US has its fair share of charming small towns, and Florida is no different.

When you book a small town vacation rental you can take things slower. Spend more time together. Never wait for a restaurant reservation or beach parking. Plus, you can see some areas off the beaten path, but no less incredible. Below are our picks for the five most charming Florida towns, perfect locales for your next vacation.

Originally Published: July 27, 2017

Top 5 Most Charming Florida Small Towns

Winter Park

Steps away from the hustle and bustle of Orlando, Winter Park offers plenty to see and do without waiting in all those lines! Dine under the stars on Park Avenue, or spend the day lounging in Central Park around the gorgeous fountains. If classical music is of interest, Winter Park is home to The Bach Festival Society that gives vigorous performances throughout the spring season. For those who prefer art history, the Charles Hosmer Morse Museum of American Art offers rotating exhibits that never get stale. Swim or kayak in Lake Virginia, or enjoy the chirping birds and fine flowers at Kraft Azalea Gardens.

Boca Grande

For an upscale spot, but still beautiful and friendly, Boca Grande fits the bill. Boca Grande is located on Florida’s west coast, known for its charming downtown, white sand beaches and world class tarpon fishing. Tour the lighthouse museum, take a dip on a secluded barrier-island beach, ride the area’s bike trails, or stroll through the Gasparilla Inn & Club which still “wows” over 100 years after its creation.

Mount Dora

Only one hour outside of Orlando, Mount Dora brings an “Old Florida” charm that can be lacking from the major hot spots. Dining in the town’s unique restaurants and shopping in the town’s quaint antique stores, you’ll feel like you’re welcomed and accepted, even if you’re only in town for a week. Strolling alongside the historic homes, you’ll notice how steeped in history Mount Dora truly is. It’s also a great place for fishing enthusiasts to get out on the water.

Fernandina Beach

Located in Northern Florida on Amelia Island, Fernandina Beach is an adorable little town with quaint shopping and upscale dining. Visitors love strolling along the pristine beaches and alongside the graceful architecture. Tourists love to take a horse-drawn carriage ride through Center Street, or use the free brochure from the visitor’s center to guide your waterfront walk.

Tarpon Springs

You’ll feel like you’re in a European dream world when visiting Tarpon Springs. The Greek influence is felt everywhere from the cuisine to the architecture. The scenic waterfront, though far from the Aegean Sea, is no less beautiful. Minutes from Clearwater, and just 45 minutes from Tampa, Tarpon Springs offers an eclectic mix of art galleries and antique stores. Considered the “Sponge Capital of the World,” the famous Sponge Docks are the area’s main attraction.


Matt Moretti has worked in the travel and vacation rental industry for over a decade. He loves helping travelers find the best places to eat, the best things to do, and the perfect vacation rental for their trip.

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