Florida's Best Small Towns for a Weekend Escape
It is well known that a weekend trip can do wonders for mental health. In a 2017 study by Enterprise Rent-A-Car, 43% of their survey participants revealed that they used a weekend getaway to escape stress. So, in 2024, why not make it a priority to take more weekends away to refresh and rejuvenate yourself after a busy week? Whether that means booking a beachfront vacation rental with your family, embarking on a solo trip to explore a charming historic town, or planning a romantic getaway to an adult-only resort, Florida’s small towns have something to offer for every type of traveler. To help you get started, here are 11 of the best small towns in Florida that may just inspire your next weekend escape.
Crystal River
For a family-friendly escape in the “Manatee Capital of The World,” what could be better than a weekend at Crystal River's best "Stay n Play" Resort? With a Tiki Bar & Grill, pristine waterfront lodging, and a gateway to meeting manatees, the Paddletail Lodge makes for an incredible adventure. Guests can rent kayaks and use the hotel’s private dock or shuttle to other Crystal River attractions Crystal River Preserve State Park for a pontoon eco-tour. To swim or snorkel with the majestic manatees Crystal River is famous for, the Three Sisters Springs (within the Crystal River National Wildlife Refuge) is also a mere 4-minute drive from the lodge.
Key West
At the southernmost point in the United States, the island town of Key West is an ideal retreat for adult travelers looking to unwind. The vibrant town boasts a variety of unique adult-only accommodations, like The Gardens Hotel, listed as “The Prettiest Hotel in Key West” by the New York Times, or the Caribbean-themed Key West Villas. The villas are especially popular since they are “just steps from Duval Street,” Key West’s charming main drag. Here you can board the Old Town Trolley, visit attractions like the Peter Lik Fine Art Gallery, and embrace Key West’s thriving nightlife scene on a Duval Bar Crawl. For a daytime activity, Key West is even more famous for its living coral reef, and agencies like Sunset Watersports offer snorkeling expeditions from morning to sunset.
Key Largo
In the upper Florida Keys, on the island of Key Largo, its namesake town is another perfect getaway destination for an undersea adventure. Known as the “Diving Capital of the World,” this island town boasts some truly dreamy dive spots. A few highlights include the iconic Christ of the Abyss statue at the Florida Keys National Marine Sanctuary, and the country’s first undersea park, John Pennekamp Coral Reef State Park. The landmark features everything from glass-bottom boat tours to snorkeling tours, meaning people of all ages can enjoy the park’s wonders.
On the other hand, if you are after an adult-only weekend in Key Largo, the 21+ Bungalows Key Largo is an all-inclusive island oasis. With 1,000 feet of shoreline surrounded by a lush botanical garden, visitors can disconnect, unwind, and savor sheltered Gulf of Mexico views. Along with unlimited dining, a zen pool and jacuzzi, and group yoga classes, visitors can take advantage of the resort’s snorkel gear for a more private undersea experience.
St. Augustine
St. Augustine is another blissful town great for families and adult travelers alike. There are endless overnight options suitable for families, like the Conch House Marina Resort Motel. Older travelers and couples instead may prefer splurging on an adults-only retreat in the heart of town at The Collector Inn & Gardens. In both cases, there is plenty to see and do for people of all ages in St. Augustine.
As the oldest town in the country, history is St. Augustine’s greatest charm. The Old Town Trolley Tour is a great way to see as much of the town as possible, and the perfect way to see the best historic sites. From a Medieval Torture Museum to Fort Matanzas (built in the 1740’s), the town transports its visitors to the past in a striking way. But St. Augustine is certainly not a one-trick pony. History, while definitely its star feature, pairs with the town’s 42 miles of beaches. From St. Augustine Beach to Anastasia State Park, quartz sand shores and shimmering waters are the perfect way to savor your weekend away.
Destin
For a beach-centered weekend away, Destin is your ticket to coastal bliss. Located on the Emerald Coast, the beaches in Destin are sugar-white and the turquoise waters are crystal clear. Luxurious accommodations like Henderson Beach Resort grant visitors a front row seat to private shores. But others may prefer more affordable options like the Beachside Inn, which is right within walking distance of The Shore at Crystal Beach Park and a short drive to Henderson Beach State Park. Whatever accommodation style you are after, Destin’s opportunities for fun are endless. From ziplining at HarborWalk Adventures to booking a boating excursion to the famous Crab Island sandbar, a weekend in Destin will have you feeling rejuvenated and excited for your next weekend away by the time Monday rolls around.
Panama City Beach
The tourist town of Panama City Beach is another Emerald Coast community with tons of beach to go around. With 27 miles of shoreline and 100 public access points, beach hopping is unsurprisingly one of the town’s most popular activities. In addition to offering a gateway to 2 gorgeous beach-based state parks (St. Andrews and Camp Helen), the town’s shored come with some other notable quirks. Dolphin sightings are in high supply, since Panama City Beach has one of the highest concentrations of Atlantic bottlenose dolphins in the world. The town’s surrounding waters are also known for their abundance of shipwrecks, many of which can be explored with companies like Panama City Diving. And to make your weekend in town as beachy as it can be, accommodations like the Beach Tower Beachfront Hotel and The Flamingo Hotel and Tower are the perfect way to savor coastal views.
Cocoa Beach
Over on Florida’s Space Coast, the community of Cocoa Beach is another beautiful resort town with a vibrant beach culture. There are tons of gorgeous waterfront hotels and lodging options to choose from, like the Hilton Cocoa Beach Oceanfront or The Inn at Cocoa Beach.
With 6 miles of public shore, the beaches are famous for their golden sands and surfing waves. If you are a less experienced surfer looking to ride these tempting waters, you can book a lesson with Cocoa Beach Surf School and hit up the world’s largest surf shop for gear. For over 60 years, the Ron Jon Surf Shop has catered to Cocoa Beach's surfer lifestyle, offering everything from surfboards to wetsuits. And for those who would prefer to savor ocean views from land, the 800-ft Cocoa Beach boardwalk is another great Cocoa Beach attraction. In addition to offering spectacular sunset views over the Atlantic, it has cute boardwalk shops and eateries like the Pier 62 Oceanfront Restaurant & Bar.
Anna Maria Island
For a more sequestered getaway, the seven-mile-long Anna Maria Island is ideal for those seeking a more laid-back weekend away. The barrier island’s namesake town, Anna Maria, is home to charming accommodations like the Sunrise Garden Resort. Perfect for beachgoers seeking a more secluded day in the sun, the resort promises a tranquil experience without the hassle of fighting for a spot in the sand. Visitors can also enjoy the island’s free trolley, visit pet-friendly shores like Palma Sola Causeway Park, and take in sights from the Anna Maria City Pier.
On the northern end of the island, Bean Point Beach is the island’s crown jewel. Considered private property not too long ago, it is now a public shore. But thanks to its previous exclusive nature, it is still somewhat of a hidden gem. So other than the more popular holiday weekends, there is a remarkable lack of beach crowds at Bean Point, and the shore has retained its private beach-feel.
Treasure Island
The barrier island town of Treasure Island has a past as exciting as its name. While its first settlers were mainly fishermen, at one time, smugglers and pirates also called the island home. And while its tales of buried treasure are merely fun local legends, today the town is a treasure in itself. The scenic Treasure Island Beach Trail makes for a glorious stroll or bike ride, while the nearby John’s Pass Village and Boardwalk has tons of family-friendly activities like the Dolphin Quest sightseeing tour. Another crowd-favorite is the The Royal Conquest cruise, a 2-hour pirate ship experience with limbo competitions, pirate stories, and treasure hunts. But before you set sail, make sure to book a room at one of the town’s treasured accommodation options, like the Ocean Club Treasure Island Hotel or Treasure Island Beach Resort.
Sebring
If tranquil lake days are more your vibe, the charming town of Sebring is the perfect weekend destination for you. Nestled between 2 lakes, the aptly named Inn On the Lakes promises scenic surroundings and a cozy yet elegant atmosphere. In addition to offering a postcard scene, Lake Jackson and Little Lake Jackson are delightful swimming holes, and the Lake Jackson Fishing Pier makes for a relaxing afternoon.
Just a short drive from the inn, other lake-based adventures await. Airboat tours of Lake Istokpoga with Airboat Wildlife Adventures are a popular excursion. And elsewhere in town, the 9,000-acre Highlands Hammock State Park is another Sebring star feature. With 9 dazzling nature trails, visitors can venture through ancient oak forests and stroll an elevated boardwalk through an enchanting cypress swamp.
Clermont
In Lake County, about 2 hours north of Sebring, the lake town town of Clermont is equally perfect for a delightful day on the water. Vacation rentals like Clermont Cabanas are located right on Lake Minneola, a gorgeous body known for its walking paths, picnic areas, and seasonal swimming at spots like Waterfront Park.
For a quirky accommodation you will not find anywhere else, the movie-themed Ever After Estate is a truly bucket list-worthy stay in Clermont. Once featured on HGTV’s “America’s Most Outrageous Homes,” the 62-acre vacation rental is a one-of-a-kind lodging perfect for families and large groups. With a private waterfall lagoon pool, a movie theater, a mini golf course, and a video game arcade, this lake-bordered vacation home is a vacation in itself.
Final Thoughts
After a week of hard work, the weekend calls for a well-deserved break. It is the perfect time to recharge, whether that means looking to relax or seeking adventure. These 11 Florida towns have something for everyone, offering the best of both worlds. Whether you prefer lounging on Destin’s stunning beaches, swimming with manatees at Crystal River, or embracing a lake day in Sebring, your getaway can be as active or as laid-back as your heart desires. But one thing is guaranteed: you will leave feeling rejuvenated and dreaming up your next Florida escape.
