Best Historic Stays: Cabbage Key Inn & Restaurant near Fort Myers

South of beautiful Boca Grande and north of the iconic sandy shores of Sanibel and Captiva, is Cabbage Key, a hidden slice of Old Florida that has been delighting guests for decades. While boaters frequent this 100-acre island, many travelers have yet to discover its charm. I’ll show you why a stop on this island, that feels like a step back in time, must be on your 2025 Florida travel list.  

History of Cabbage Key  

The island’s history stretches back to 10,000 B.C. In fact, geologists say the island has not completely flooded since the Ice Age! It’s one of several islands that sprinkle Pine Island Sound along the west coast of Lee County.  

The Calusa, an indigenous Southwest Florida tribe, created a large shell midden on Cabbage Key. In the 1930s, famed mystery writer Mary Roberts Rinehart and her family built their winter estate atop the shell mound, which is more than 30 feet above sea level.  

For those unfamiliar with Rinehart’s work, you may be surprised to learn that her play The Bat (1920) ran on Broadway and was Bob Kane's inspiration for Batman.  

Today, the Rinehart winter estate is the historic Cabbage Key Inn & Restaurant and is one of Florida’s most unique lodging experiences.  

In the six inn rooms connected to the restaurant, you’ll find original hardwood floors, archival photos of Cabbage Key, air conditioning, TV, and private baths. While a treat to visit Cabbage Key is being disconnected, Wi-Fi is available in the inn.  

The inn is especially perfect for those who want to be at the center of the action on Cabbage Key.  

For a more secluded retreat, six charming cottages provide a quiet escape. I stayed in the Cabbage Patch Cottage, a cozy two-bedroom, two-bathroom retreat with rustic cedar walls and a private dock. It was just a short walk from all the activity, yet still felt like my own peaceful slice of paradise.  

The Dollhouse Cottage is another popular choice. Originally built in the early 1930s for the Rinehart children as a playhouse, the Dollhouse is a one-bedroom air-conditioned cottage with a king bed, basic TV, small refrigerator, coffee maker, and a living room. The cottage is situated on the water with a private dock, a screened front porch, and a breathtaking view of Pine Island Sound.  

Dining on Cabbage Key  

One of the most famous reasons to visit Cabbage Key is its legendary restaurant and Dollar Bill Bar, a must-stop for boaters cruising along the Intracoastal Waterway. Over the years, the restaurant has welcomed its fair share of notable guests—including Jimmy Buffett.  

A visit isn’t complete without ordering the famous Cabbage Key Burger and pairing it with the island’s signature cocktail, the Cabbage Creeper—a tropical drink that has a sneaky way of catching up to you!  

While dining, don’t forget to take part in one of Cabbage Key’s most well-known traditions at the Dollar Bill Bar: taping a dollar bill with your name onto the restaurant’s walls or ceiling. This practice, started decades ago by fishermen, adds to the charm and history of the space.  

What Else to Do on Cabbage Key  

For a breathtaking perspective of Cabbage Key, climb to the top of the island’s historic water tower. Built in the 1930s as part of Mary Roberts Rinehart’s estate, this iconic structure offers panoramic views of Pine Island Sound and the surrounding islands, including Useppa.  

And, of course, you need to prove you visited Cabbage Key! Shop for souvenirs at the gift shop by the dock—hats, shirts, and other keepsakes make for great mementos.  

And, indulge in sweet treats at the Cabbage Key Creamery, offering local ice cream flavors in freshly baked waffle cones. The smell is heavenly!  

Beyond the inn, restaurant, and cabins, Cabbage Key’s quieter side offers a chance to immerse yourself in nature. Explore scenic trails along the water and through the interior of the water.

And, Just a short paddle or boat ride away is Cayo Costa State Park, where seven miles of pristine beaches await. This area is a shell collector’s paradise, with clear waters and soft, sandy shores perfect for a peaceful escape.  

The island is accessible only by boat, but that’s part of its magic. If you don’t have your own, water taxis and private charters can bring you directly to Cabbage Key from nearby marinas. For booking and more information, click here or call 239-283-2278.

Reservations for cottages and rooms at the inn cannot be made online. You must call for availability. Add it to the list of the old-school charm you’ll find here!  

Trust me, this spot is worth the effort. Enjoy!