Captiva Island Inn: An Alluring, Unique Stay in Southwest Florida

Delightful digs with a little history and a lot of charm

By
Fort Myers Local Expert

There’s something about the carefree buzz on Captiva Island's Andy Rosse Lane that you just want to be a part of. The small road runs through the heart of Olde Captiva, where Captiva Island Inn is a prominent fixture.

Receiving its historical preservation designation in 1998, the Fort Myers area inn has been known by different names, survived hurricanes and had many prominent guests in its more than 60 years on the barrier island. In 1999, Fort Myers businesswoman Sandy Stilwell purchased the property, giving it that extra bit of TLC that it is known for today.

This bed and breakfast takes up real estate on both sides of the lane that people saunter safely across, visiting restaurants, coffee shops, galleries and an old general store. The funky yet sophisticated, laid-back island vibe is sure to unwind even the most high-strung visitor.

Colorful cottages and galleries create a fun, festive vibe on Andy Rosse Lane
Photo courtesy of Ultimate Island Guide

Don’t expect any generic, hotel chain features at the inn. The interiors of the 18 cottages are not perfect, but they are perfectly charming, with things like uneven floors, low ceilings and colorful, unique décor.

The Orchid Cottage is one of the most popular and historic, as famous aviator Charles Lindbergh and wife Anne Morrow stayed here. Low lying, with baseboards that look like waves, it has lots of unique cutouts and architecture.

Mrs. Lindbergh’s favorite flower was the iris, and the inspiration for the name of one of the more spacious accommodations: the Iris Villa. This two-bedroom cottage is full of antiques from around the world and has an upgraded kitchen.

Then there is the Love Shack, a small room that at one point during the inn’s history was rented out by the hour. Couples find great humor in the checkered past of this cozy room, now redone in shades of violet with white accents.

The main house is more modern and a most excellent space for large families, bridal parties, retreats and other such getaways. The five bedrooms and two kitchens grant lots of flexibility.

If you don’t want the entire house, pick a floor. The third floor has a large honeymoon suite with a private balcony, a kitchen and a second bedroom. On the second floor, you’ll find wide-open space with a comfortable living room, a fully equipped kitchen and three bedrooms.

The refreshing pool is perfect for parties or relaxation
Photo courtesy of Ultimate Island Guide

The guest pool is located behind the house, while the stunning, shell-lined beach is just 360 steps west. Beach chairs are free. The bay, where you can catch sunset cruises, dolphin tours and fishing charters, is just 360 steps east; yes, the island is that narrow.

Even though the main house has two kitchens, your complimentary breakfast is served via vouchers to dine at two of the numerous restaurants on property. RC Otters and Keylime Bistro serve an appealing breakfast lunch and dinner, while offering live music day and night; linger as long as you want.

And if you want to explore other areas of the island, take the free S Car Go Shuttle. (Hint: It looks like a snail.)

Not only popular with guests, Captiva Island Inn is also a hot spot for catalogue and magazine photo shoots. Check out the calendar of events for the island, and visit during the Songwriters Festival, the Captiva Triathlon or the Captiva Holiday Village in December, where you’ll be entertained by golf cart and boat parades.

Prices at this captivating property have quite a range. Depending on the time of the year and which cottage or room you choose, expect to pay anywhere from $99 to $450 a night and to leave with memories that are priceless.


About Gina Birch

Gina Birch is a Southwest Florida radio and TV personality with the inside scoop on hottest local places to stay. 

Read more about Gina Birch here.

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