The 16 Most Charming Small Towns in Florida

Established more than 450 years ago, this northern Florida town is as charming as it is old (we mean that as a compliment). Located on the Matanzas River, St. Augustine is brimming with history intertwined with European flair and Southern hospitality. Roam cobblestone streets lined with palm trees and take in the Spanish Renaissance Revival–style architecture.

Where to stay: Filled with historic charm, Casa Monica Resort & Spa is one of St. Augustine’s best hotels. Beyond the top-notch accommodations, the famed Florida hotel, originally constructed in 1888, is located at the heart of the city’s Historic District and within walking distance to destinations like the award-winning San Sebastian Winery and Castillo de San Marcos.

The upscale resort town on the Gulf of Mexico feels like another world entirely, complete with serene beaches, top-notch dining and some of the most gorgeous sunsets we’ve ever seen. If you go, make it a point to visit the Naples Pier, which offers striking views of the ocean, and pop into Jane’s Café on 3rd for a mimosa, gluten-free avocado toast and a stack of sweet pancakes.

Where to stay: This one’s a no-brainer: The perfect place to stay during a quick getaway to Florida’s west coast is the Naples Grande. About ten minutes from downtown Naples, this affordably priced hotel includes everything you’ll need for the ultimate vacation. The sprawling property features more than 400 beautiful rooms, three glistening pools, stellar restaurants and bars and even a waterslide for the kids. It’s only a short walk to a gorgeous private beach, complete with cabanas and an oceanfront Greek restaurant, too.

At just over a mile long, Micanopy is Florida’s self-proclaimed antiques capital. It’s known as a rural, sleepy town just south of Gainesville, which is why it earned the nickname of “the little town that time forgot.” With a population of about 600, the busiest road (Cholokka Boulevard) is lined with typical Florida architecture, old oak trees covered in Spanish moss and antique storefronts.

Where to stay: Ever dreamed of vacationing at a mansion? Same. That’s where Micanopy’s Herlong Mansion comes in. This adorable bed-and-breakfast spot greets every guest with a glass of wine and a warm cookie. The rooms are chock-full of old Florida glamour, which makes sense considering the home itself dates back to the early 1840s. (If you’re recently engaged, Herlong is known as one of the area’s most beautiful places to host a wedding, too.)

It’s impossible to say which Florida town is the prettiest (there are just too many to count), but Sanibel is definitely a top contender. Just off Florida’s peninsula on the Gulf of Mexico, this place is a perfect seaside vacation spot, replete with miles of crystal-clear waters for boating, fishing and snorkeling—plus thousands of patterned seashells waiting to be collected.

Where to stay: Along the coast, Sanibel Siesta on the Beach offers spacious, two-bedroom suites with access to a private beach on the Gulf of Mexico. It’s a great place to get the most out of your trip to Sanibel, giving you direct access to the beach as well as other water-centric excursions. It’s also within walking distance to area restaurants, bars and shops.

Hop in the car and drive to Key Largo. This oceanfront spot is a welcome change of pace from Miami, offering picturesque sunsets, charming restaurants and quiet hotels. Bring a couple of bathing suits (and lots of sunscreen) and get ready to spend a few days on the water, whether that means fishing, sailing, jet skiing or swimming.

Where to stay: We love Playa Largo Resort & Spa, a luxury Key Largo resort replete with secluded shoreline and stunning views of the Florida Bay. With on-site restaurants and bars, various entertainment and a seemingly never-ending coastline, Playa Largo features everything you need for a tranquil getaway.

Looking for a quick getaway that unites your love of the Florida Keys with beachy cocktails, seaside excursions and tropical eats? Just under two hours from Miami, the four islands of Islamorada are known for having an upscale, small-town vibe with museums, seafood restaurants, boating and lots of sunshine. Psst: Beaches aside, Islamorada is home to not one but two funky breweries worthy of a visit—Florida Keys Brewing Co. and Islamorada Beer Company both brew local beers with Keys-inspired ingredients, from key limes to starfruit and honey.

Where to stay: For the best of both the beach and boating, book a villa at Hadley House, which is located near the center of Islamorada. This remodeled boutique is set up near some of the Key’s most popular restaurants and attractions, with cocktails, water sports and other activities like breweries and museums all less than a five-minute drive away. With a location practically sitting on the sand, guests of the hotel can take advantage of complimentary on-site kayaking and paddle boarding or (for an added charge) a private jet-skiing tour of the surrounding keys.

St. Pete is Florida’s most underrated gem. It’s got all the fixings for an epic escape from Miami (think gorgeous beaches, cooler weather, stellar restaurants and top-notch art museums). Plus, downtown St. Petersburg is less than ten miles from St. Pete Beach. But because there’s virtually no traffic in the area, the drive is just under 15 minutes. That means you get to experience the excitement of downtown but squeeze in a few hours a day on the sand too.

Where to stay: Booking a room at the Kimpton Hotel Zamora will guarantee you an amazing stay. About ten minutes from downtown St. Pete, this boutique Mediterranean-inspired property near the beach is full of expansive (and affordable) suites with balconies overlooking the Gulf of Mexico. The rooms are modern, cozy and dog-friendly (rates start at $169 per night). It also has a first-rate rooftop bar that makes for an epic sunset viewing spot.

Located along Florida’s Treasure Coast, Vero beach is a sophisticated getaway offering scenic beaches, charming museums, nature attractions and luxurious accommodations. This charming destination, often referred to as the “Hamptons of Florida,” is the perfect place to decompress. If you go, make sure to get the full experience by renting a golf cart to explore this unique seaside community.

Where to stay: Gloria and Emilio Estefan fans, anyone? You’ll want to stay at Vero Beach’s Costa d’Este. This glamourous hotel brings Miami-flair to the Treasure Coast with everything from a luxurious spa retreat to fine dining to craft breweries to boutique shopping. One thing’s certain: You’re in good hands with the Estefans at Costa d’Este.

Sebring is a hidden gem, nestled in the center of Florida’s peninsula. Often referred to as “The City on the Circle,” Sebring offers a wide range of exciting tourist attractions, accommodations, fine and casual dining and shopping in the Downtown Sebring Historic District. Visitors can even hop on a hot air balloon and ride it over Sebring’s magnificent freshwater lakes. Um, count us in.

Where to stay: You can’t go wrong with booking a room at the Inn on the Lakes. Restaurants and bars, world-class golf courses and walking distance from Sebring’s historic area, the Inn is an excellent choice for anyone looking to immerse themselves in all that this Florida city has to offer.

We know, we know: Coconut Grove is practically in our backyard, so you may be wondering why you’d bother to spend a few nights here. But it feels like another universe compared to Greater Miami (plus there’s no chance of pesky travel delays). As Miami’s oldest neighborhood, Coconut Grove offers no shortage of things to do, from roaming Italian-inspired gardens to drinking sauvignon blanc frosé to indulging in honey-infused spa treatments. Yep, this plot of bohemian land has it all.

Where to stay: For top-notch luxury, book a room at the Ritz-Carlton Coconut Grove. This upscale, villa-like hotel features gorgeous floor-to-ceiling marble bathrooms (hello, home inspo), bright balconies overlooking the bay and a next-level spa featuring organic Florida Keys honey in almost every signature treatment.

With beaches spanning for more than 15 miles, Captiva Island is a tropical paradise. Known for its quaint, tropical atmosphere, Captiva is home to over 250 types of shells, unique wildlife and enchanting sunsets. You can fill your days by exploring nearby wildlife preserves, booking a private fishing excursion or unwinding on white-sand beaches.

Where to stay: The South Seas Island Resort in Captiva Island blends the best of old Florida with modern elegance. Surrounded by a 330-acre wildlife preserve, spend your time kayaking, sailing, boating and relaxing on the sand. Enjoy playing golf? South Seas has that too, featuring a picture-perfect course along the water.

Established in 1562, Amelia Island is a timeless city with rich history. It’s home to more than 13 miles of quiet beaches, next-level golf courses, shore excursions and a historic district replete with ghost tours (!!!), art museums and waterfront restaurants. Looking for a slice of heaven? Head to Fernandina Beach for date night and explore the sparkling shoreline.

Where to stay: The Ritz-Carlton Amelia Island is worth the splurge here. With more than 400 rooms and four restaurants, plus on-site tennis, an unbelievable spa and an 18-hole golf course, we wouldn’t blame you if you never left the resort’s grounds.

Would this list be complete without including this chain of islands off the tip of Florida? Colorful pastel-painted beach houses, swaying palms, Ernest Hemingway’s historic home and the rowdy bars of Duval Street—Key West might not be as “small” as the others, but it’s always worth a visit.

Where to stay: For the best of both the beach and the city, book a room at Oceans Edge, located in Key West’s Stock Island neighborhood. It’s one of Key West’s newest and largest luxury properties, featuring 360-degree waterfront views, six glistening pools, complimentary paddle boarding and kayaking, and an open-air waterside restaurant and bar.