A love song to Victorian architecture, the Southernmost House Historic Inn is one of the most photographed buildings in Key West. Painted in pale sea foam, cream, pink and burgundy colors, the 1896 home, with its Queen Anne-style turret, really catches the eye of anyone walking by. From across the street, you can marvel at its Tiffany stained-glass canopy and miles of decorative trim. No doubt this bed-and-breakfast is an island wonder. Sequestered on the quiet end of Key West’s main drag, steps from the famed Southernmost Point buoy (another most- photographed landmark), the house provides a welcome respite from the hubbub of Duval Street, where numerous bars encourage foot traffic till the wee hours of the morning. Guests find the B&B enchanting and peaceful. Just one peek inside will leave any architecture or history buff giddy with delight. Gaze up and take in the stately chandeliers with sculpted ceiling medallions lighting the way to hidden balconies. Turn your head and stainedglass windows frame hypnotic views of the Atlantic Ocean, and when you meander through the house, you’ll spot a rose-carved telephone gossip bench.
Much of the home’s history is steeped in local lore. Ernest Hemingway’s saddle still hangs in the lobby; a hole in a window represents a bullet meant for Al Capone. The heliport built for King Juan Carlos of Spain now doubles as a sun deck. During Prohibition, the house served as a speakeasy with gambling and, in the early 1940s, a Cuban nightclub. You can almost sense the spirits of famed revelers like Tennessee Williams and Truman Capote as you climb the creaking wooden stairway. In the 1950s, the Ramos family, prominent merchants from Spain, made it their home and feted U.S. presidents like Harry Truman, Dwight D. Eisenhower and John F. Kennedy.
It’s this air of distinction that has guests coming back to the house. Kathy Snell, an avid traveler from Ocean City, Maryland, plotted for months to score a weeklong stay in the main house’s Room 201, highly coveted for its oceanfront views and private balcony. “This place is so quaint, with the high ceilings and crown moldings, and we love the rich history,” she says. “Plus, we feel like we have our own private pool.”
Although the island’s public South Beach is across the street, the tranquil infinity pool in the house’s backyard mesmerizes most guests. It looks as if it flows straight off into the sea — and it has a six-seat pool bar, where bartender Rachel muddles sugar and mint for a steady stream of mojitos. Guests soak up the rays and chat about life in the Keys. Gesturing to the hammock swaying between two palm trees and the sailboats off in the distance, one lounger comments, “I never get tired of this.”
A metamorphosis in 1996 turned the home into a guesthouse with 18 rooms and suites, complete with flat-screen TVs, mini-fridges and floor-to-ceiling glass showers tastefully integrated with antique tufted chairs and claw-foot tables.
Despite its island size, Key West is brimming with places to explore, and a rental bicycle fares well on the narrow, congested streets. If you want to play tourist, join Lloyd’s Tropical Bike Tour. A true Keys character, Lloyd Major leads a small group down shaded side roads, through parks and into a secret rain forest you’d never find on your own.
For dinner suggestions, the inn’s concierge, Lloyd Daniels, is hip to the buzz around town. The latest hot spot, the Flaming Buoy Filet Company, is tucked away in a quiet residential neighborhood and has a mere 10 tables. Co-owners Fred Isch and Scot Forste serve a trio appetizer of Key West bounty: smoky-sweet grilled Key West pink shrimp with a tart lime chutney; tuna ceviche marinating in fresh watermelon; and Florida lobster mac with three cheeses. After a night out, the B&B’s four- poster bed will feel heavenly, and you’ll awaken refreshed to a sunrise mirrored on the water.
More Great Bed & Breakfasts
Apalachicola
Stay in the main house of the Coombs Inn, where elegant wood treatments enhance the walls, floors and staircase. The Mr. & Mrs. Coombs room has a four-poster bed and a Jacuzzi.
Gainesville
Cindy and Joe Montalto created Gainesville’s Bed & Breakfast District when they restored their 1885 Victorian mansion, the Magnolia Plantation, and added cottages and gardens.
Palmetto
Corralled by a white picket fence, the Palmetto Riverside Bed and Breakfast faces the Manatee River. Belgian innkeepers Wim and Mieke Lippens handpicked its French antiques.
St. Augustine
Each of the eight rooms at the historic Inn on Charlotte has an incredibly regal bed. Henry Flagler’s Verandah Room, with its king-size, four-poster bed, plus Jacuzzi and balcony, is our favorite.
St. Petersburg
The Dickens House pays homage to the arts-and-crafts, mission style, and is known for its breakfasts of orange zest French toast.
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