Where to Stay in Key West This Winter, Based on Your Travel Personality
Where to Stay in Key West This Winter, Based on Your Travel Personality
When winter’s chill sets in, there’s no better place to escape to than the sun-soaked paradise of Key West. Known for its vibrant history and unique charm, Key West welcomes a variety of travelers from around the world – all with different travel styles and preferences.
To suit their distinct personalities, we have found the perfect backdrop for their winter escape at Key West Historic Inns – an enchanting collection of five historic properties nestled in the heart of Old Town Key West. These cherished sanctuaries each offer an authentic Key West experience, blending the spirit and tales of the past with modern-day charm. From colonial wood-frame houses to stunning Queen Anne architecture, the Inns connect travelers to a slice of the best of the island.
Here’s how to choose the Inn that best suits your travel personality this winter:
For the Nature Enthusiast: Ridley House
Inspired by the legacy of naturalist Richard Kemp, Ridley House offers a refined yet rugged retreat in lush surroundings. With just 23 exclusive rooms, this upscale escape blends untamed beauty with sophisticated charm. Imagine afternoons spent under the shade of swaying palms, savoring a Cypress Sangria at the daily soiree. The Inn’s Bahamian Eyebrow architecture and Victorian details invite you to step back into the Key West of old, while its modern boho aesthetic keeps things fresh. For book lovers, the cozy Library Room—filled with hundreds of titles—is the perfect hideaway to curl up and dream of your next adventure.
For the Social Butterfly: Lighthouse Hotel
Located just steps from the iconic Key West Lighthouse and Ernest Hemingway’s former home, Lighthouse Hotel is the ultimate spot for travelers seeking a lively and social atmosphere. Formerly a pioneering LGBTQ guesthouse, the property exudes a vibrant energy that’s impossible to resist. Its poolside bar, Isabel’s, is famous for signature mojitos and a touch of historical intrigue—including tales of a hidden stash of gold discovered in the 1980s. With 44 guestrooms and a communal vibe, it’s perfect for gatherings with friends or meeting fellow travelers in a dynamic setting.
For the Romantic Soul: Ella’s Cottages
If cozy nooks and bohemian charm are what you crave, Ella’s Cottages is your dream retreat. Once home to Cuban cigar makers and later Navy personnel, this quaint property celebrates Key West’s maritime spirit with private patios and 22 cottage-style accommodations. Daily Merlin’s afternoon tea, featuring lavender- and honey-infused shortbread, adds a whimsical touch that’s perfect for couples seeking a romantic escape in Old Town. Whether you’re strolling hand-in-hand through nearby streets or savoring quiet moments in your private bungalow, Ella’s Cottages provides a serene, storybook setting.
For the Creative Spirit: Winslow’s Bungalows
Winslow’s Bungalows, named after artist Winslow Homer, combines vibrant interiors with a resort-like atmosphere. With three outdoor pools, brick-paved pathways, and lush tropical grounds, it’s an inviting retreat for couples, families, and friends. Winslow’s artistic heritage adds an air of creativity, while amenities like live poolside music and pirate tokens redeemable at the Bungalow Bar keep the vibe playful and fun. Whether you’re lounging poolside with a cocktail or exploring Key West’s cultural offerings, this property captures the island’s eclectic charm.
For the Adventurer: Fitch Lodge
Just steps from the historic Key West Seaport, Fitch Lodge is a haven for adventurers and history buffs alike. With its Victorian-inspired architecture and a rich nautical past, this Inn offers a touch of bohemian flair perfect for explorers. Daily breakfast bites and “Fitch-Wiches,” a refreshing lemon vodka drink, set the tone for your island adventures. Whether you’re embarking on a snorkeling trip or wandering the historic seaport, Fitch Lodge provides the perfect home base.
Why Choose One When You Can Have It All?
Each of Key West Historic Inns offers something truly unique, yet they all share a commitment to personalized service, lush surroundings, and unforgettable culinary experiences. Whichever you choose, you’ll be immersed in the vibrant culture and rich history of Key West. So, what kind of traveler are you this winter? Let these Inns set the stage for your tropical escape.
