To really get a feel for Old Florida, spend the night at one of the hotels and inns that has truly stood the test of time. These four historic stays have been part of Florida’s story for well over a century, and you can still check in and experience their charm today.

Bonita Springs, between Fort Myers and Naples on Florida’s Gulf Coast, is full of surprises and Old Florida charm. It’s home to a quaint downtown district, beautiful beaches, and a historic hotel that’s the perfect home base to explore all that the area has to offer.

Stuart, a small city about 45 minutes north of West Palm, has earned the title of “America’s Best Coastal Small Town” from USA Today for good reason. It has a super cute downtown, fascinating coastal history, and a unique historic inn. Here are five essential stops in Stuart. 

Now in its 112th season, The Gasparilla Inn in Boca Grande on Gasparilla Island still feels like a hidden treasure. The “Grand Dame” of this quiet barrier island continues to hold onto its timeless charm while making a lasting imprint on the community.

A Key West icon is shining brighter than ever. La Concha Key West, now part of the Autograph Collection, recently completed a $35 million renovation that honors its storied past while introducing a fresh, elevated experiences. Set in the heart of Key West’s historic district, this legendary landmark puts you right in the middle of it all, with the buzz of Duval Street just steps away.

The most iconic place to stay in the nation’s oldest city is Casa Monica Resort & Spa. You wouldn’t know it now, but this luxury hotel has been overlooked, shuttered, and even used as a government building during its 130+ year history. Thankfully, in recent decades, it’s been restored to its original grandeur and is now one of the most sought-after places to stay in St. Augustine.