Old charmers

Key West Historic Inns (Old Town)

GETAWAYS • Key West

There’s a collection of five historic inns scattered across Key West’s Old Town that have lived many lives. While some were built in the 1880s by the island’s first settlers, the modern provenance dates to 2018 when a San Francisco-based private equity firm scooped all of them up for $109 million from innkeeper Julie Fondriest, in one of the island’s largest real estate transactions ever. In 2021 the collection reopened as a Kimpton property, having endured a sweeping refresh to guest room interiors (while maintaining their historic bones and character). Last January, under new management again, the collection rebranded as Key West Historic Inns.

I’ve been checking into these inns for the last 20 years, and I can confidently say that this current iteration is the best they’ve ever been. The hospitality is warm and personalized, and the properties’ quirky charms gel beautifully with modern, stylish rooms and an upgraded culinary program for a delightful stay. While each inn offers a slightly different vantage point on Old Town (and a range of price points), they all feature lushly landscaped courtyard swimming pools and that sublime feeling of Key West residential living.

Most of my recent stays have been at the adults-only Ridley House (above), one of the late 19th-century homes on Caroline Street — an unbeatable location — originally built by a sponger who classified the native Ridley sea turtle. Especially great are the front rooms overlooking the street, which grant exclusive access to a furnished porch — there’s simply no better place to lounge and watch the world go by in Key West.

Among the other inns, I’m partial to the Lighthouse Hotel on Whitehead Street for its conch cottage compound layout and location by the namesake lighthouse in Bahama Village, directly across the street from the Hemingway House. There’s also Winslow’s Bungalows, the largest inn (at about 90 rooms) with the best pool, set on busy Truman Avenue, as well as Ella’s Cottages on Simonton Street and Fitch Lodge at the far end of Eaton Street, which tends to be the most budget-friendly.

The updated guestrooms sport contemporary design with a subtle nautical motif in a palette of soft blue and cream, featuring voluminous, Balinese-inspired dark hardwood furniture and wooden beaded chandeliers. Among the many room types spread across five properties, there’s still a feeling that no two are exactly alike. The most interesting touches are preserved from the original properties, like stained glass windows, a spiral staircase leading to a loft, decorative wainscoting, or a built-in bookcase spanning an entire wall.

While Key West Historic Inns operates more as bed and breakfast without proper restaurants onsite, the latest rebrand brought much-needed dining improvements. At Ridley House and Winslow’s Bungalows, a dedicated chef is on site every morning to prepare eggs made to order alongside a thoughtful breakfast buffet. At Ella’s Cottage, breakfast baskets are delivered to rooms every morning, while Fitch Lodge provides freshly made breakfast sandwiches in a grab-and-go setting. Winslow’s Bungalows and the Lighthouse Hotel both feature laidback poolside bars serving Key West-inspired cocktails (Winslow’s also serves a light lunch). And the properties lacking bars still offer complimentary daily curated happy hours, ranging from sangria to vodka lemonade spritzes.

One thing’s for certain, you can make your own personal paradise at any of these charming inns — I know I have, many times over. –Shayne Benowitz

→ Key West Historic Inns (Old Town) • 601 Caroline Street & other locations across Old Town • Rates from $549/weekend night king at Lighthouse Hotel.