13 Truly Charming Lakeside Towns in Florida

For some, Florida is all about soaking up the sun on the beach or spending the day fishing on the Gulf. Yet, the beautiful weather makes it ideal for lakeside retreats, too. If you’re looking for relaxing, even stunning experiences, there are some towns in Florida you can't miss.

These are the most charming lakeside towns in Florida that are worth stepping up your travel game to explore. It’s hard to beat their allure and character.

Check out the top lakeside towns in Florida for your holiday trip.

Winter Park is only about a 30-minute drive from Orlando (but it seems worlds away). This community has several lakes, perfect for everything from largemouth bass fishing to boating.

It also has a lot of history and art, from the Charles Hosmer Morse Museum of American Art to the Albin Polasek Museum & Sculpture Gardens, which are quite stunning.

A smaller town, Tavares, sits on the shore of Lake Dora. The historic courthouse sets the stage for the downtown area, but this is also a modern community. The more revitalized areas of the community have lots of eateries and smaller shops.

The city, which has become one of the most sought-after “seaplane cities,” makes it easy to sit and watch the planes as they come in. There's also a lot of nature nearby, including trails and fishing along the Dora Canal.

Mount Dora is a fun, relaxing destination on a six-mile-long lake. It feels like a small town with a romantic, laid-back vibe.

There’s plenty to do, including visiting the Grantham Point Park lighthouse. You can also visit during the Mount Dora Arts Festival each February.

Sitting on a lake of the same name, the community of Eustis has a beautiful historic downtown area to explore, but the lakefront area offers a dock for your boat and long walks along a clean, well-maintained lake.

Dozens of restaurants are present here, and the boardwalk allows you to check out the various street festivals, whether they are antique-inspired, car shows, or bike shows. Catch the breezes off the lake as you do.

About 22 miles west of Orlando is the lakeside community of Clermont. This community is very much focused on its waterfront area with trails and parks to explore. Boating, fishing, and water sports are common here.

Some spend their time sunbathing on the beach while others explore the historic downtown area and watch the sunset.

When you want to relax in a small town on the water, check out Howey-in-the-Hills. All of the nature here, from the herons to the fish, make it quaint and charming.

The marina and some of the area's higher-end restaurants are fabulous. If fishing, golf, and sunbathing sound good, this is the place to be.

A smaller town in Highlands County, Lake Placid sits on Lake Istokpoga, which is a large, fabulous destination for fishing, boating, and hiking adventures.

Check out the murals throughout the city, visit some of the boutique shops, or bike around the region. The farmer’s market, art events, and car shows keep you busy most weekends, too.

The Sebring Downtown Historic District is one of the numerous beautiful spots you’ll find in Sebring. Don’t stop there, though. You can explore the rivers and lakes throughout the area.

You can go for a hike in the nearby citrus groves or play some golf. Various small-town shops and restaurants are available throughout the city, too.

Here’s another option when you want to be on the lake but close enough to Orlando for a day at the parks: Lake Mary. Numerous small lakes and ponds dot the city’s landscape.

There are some luxury hotels here and ample shopping. A more suburban-style getaway, this lakefront town is a good option for those looking for modern amenities close to the water.

For outdoor adventure in a charming, older-feeling community, head to Lake City, an hour or so to the west of Jacksonville.

There’s plenty to do outdoors, from tubing down the Ichetucknee River, checking out the Wes Skiles Peacock Springs State Park, or spending the day paddling along the Suwannee River.

For those looking for a bit more of a luxury lakeside experience, head to North Lake. It’s a more exclusive area with some fabulous cottages (there’s an RV park here, too).

Once there, swim at the pool, head to one of the local casual dining restaurants for a hearty dinner, or walk the trails around the waterfront. You can also fish on Lake Okeechobee.

A bigger city than some on this list, Leesburg is a community right between Lake Harris and Lake Griffin. It provides direct access to the Ocklawaha River for boating, paddling, and ample relaxation on the waterfront.

Ask the locals about hidden fishing spots or explore the nature preserves before catching a meal at one of the locally owned restaurants.

A trip to DeFuniak Springs brings with it lots of Victorian architecture in the historic downtown area. It’s not just a beautiful area, though (make sure you check out the Circle Dive Historic Center to learn more).

You can go for walks along the waterfront, hike in Lake Stanley Park, or take a boat tour to explore the entire area. A few spas and shops exist here, too.

Lakeside towns in Florida, small or large, are everywhere. In a state with over 7,500 lakes, it’s possible to find something special in just about every corner here, from upscale living and modern amenities to simple, quiet days by the waterfront. 

Just make sure to bring your best travel credit cards to really maximize your trip.