A collection of five historic inns across Key West’s Old Town, each boasting a small courtyard pool surrounded by lush foliage. They’re full of idiosyncratic charm and newly updated contemporary interiors in a nautical motif.
Location 8/10
With inns dotting nearly every corner of Old Town, take your pick from the adults-only Ridley House in an unbeatable location on Caroline Street, the Lighthouse Hotel by Key West’s historic lighthouse on Olivia Street and Ella’s Cottages on Simonton Street. Slightly more peripherally, Winslow’s Bungalows is the largest inn with about 90 rooms set on busy Truman Avenue, while Fitch Lodge is the most budget-friendly alternative situated near the northeast end of Eaton Street.
I’m personally partial to Ridley and Lighthouse, but so long as you’ve got a bicycle (rentals are available on property), the best of Key West’s Old Town is at your fingertips from any of these properties.
“I’ll register under a made-up name at a little hotel on the coast… My life will be like the room, cool—shadowy cool and—filled with the murmur of—rain… I will receive a check in the mail every week that I can count on.”
Woman in ‘Talk To Me Like The Rain And Let Me Listen’ by Tennessee Williams, 1953
Design 8/10
Tucked away inside lushly landscaped compounds of historic conch cottages with their charming residential appeal, I’ve been a fan of these properties for as long as I’ve been coming to Key West (almost 20 years). Recently, Kimpton Hotels briefly took over and led the redesign of guest room interiors and common space furnishings. Each property retains its historic footprint and architecture and has its own particular feeling of a private paradise oasis.
Amenities & Hospitality 7/10
Service is friendly and laidback with many longtime employees going back to the original ownership. And while the courtyard swimming pools are inviting, they’re small and often covered by shade early in the day. The best way to cool off in the water and enjoy Key West’s sunshine is to visit the beach at Fort Zach or embark on a snorkel trip to the reef (I’m a Fury girl for life). The front desk attendant or concierge can arrange tours and bike rentals.
Rooms 8/10
Updated guest rooms are contemporary with a vaguely nautical design scheme in a palette of soft blue and cream with voluminous, Balinese-inspired dark hardwood furniture and wooden beaded chandeliers. Most of the bathrooms have also received updates with glass showers, blue tile walls and herringbone-patterned marble floors. With many room types spread across five properties, there’s still a feeling that no two rooms are exactly alike. The most interesting touches are preserved from the original property, like stained glass windows, a spiral staircase leading to a loft, decorative wainscoting or a built-in bookcase spanning an entire wall.
Food & Beverage 5/10
There’s no onsite restaurant, but every property offers complimentary continental breakfast with items like toast, cereal and fruit. Winslow’s Bungalows and the Lighthouse Hotel feature laidback poolside bars serving Key West-appropriate cocktails, like rum runners and margaritas, along with beer and wine.
Value 8/10
Rates from about $299 in low season and $499 in high. Book
The Bottom Line
Check into a Key West Historic Inn and experience the island as the locals do: from a lush cottage complex in Old Town.
Contact
725 Truman Avenue & other addresses; 305-294-5229; keywesthistoricinns.com
