Caroline Street holds a personal connection for the Spottswood family, as several generations of that clan grew up on that road in Old Town Key West, including the three oldest Spottswood sons, Bill, Jack and Robert.
Jack and Robert Spottswood still call Caroline Street home and now live down the block from the family’s latest hotel, the Grand Maloney Hotel.
The Spottswood Hotels company has converted the brick-facade mansion at 529 Caroline St. into the island’s newest boutique hotel. The Grand Maloney Hotel — a six-bedroom restored home from the late 19th century — reopened in May, ushering in a new era in Key West-style hospitality with the completion of its nearly two-year restoration and renovation process.
“The block is special to us and needs to be protected, restored and shared,” said Billy Spottswood, president of Spottswood Hotels and son of Bill.
The historic estate was purchased in 2019 by Spottswood Hotels and has been restored and named after Walter C. Maloney, an early member of the Spottswood family who was elected Key West mayor in 1846.
“This project was a special one. Multiple generations of our family have grown up on this block, so it was important for our team to design an experience that preserves history while also embracing a modern aesthetic and contemporary approach to service,” Billy Spottswood said. “Elaine (Billy’s cousin) did an excellent job leading our design and executing that vision.”
The first home at 529 Caroline St. was built by a sponger named A.G. Arapian prior to 1850, Billy Spottswood said. The house burned down in a citywide fire and the current structure was rebuilt in 1870s and made to be fire resistant, hence the unusual brick facade facing Caroline Street.
The hotel’s style bestows each guest room and common space with its own personality. Throughout the property, guests are treated to statement furnishings that blend the hotel’s historic materials with new luxury finishes and bold colors, such as a floor-to-ceiling bright yellow-tiled shower, an in-room original brick fireplace and colorful botanical print wallpaper. The Grand Maloney also features a newly-built swimming pool and outdoor space offering an additional area for groups to entertain. A testament to the attention to detail put forth by designer Elaine Spottswood, guests will find there are no two rooms or spaces alike.
“It was a privilege to salvage what original pieces we could, such as brick, interior molding and 150-year-old wood floors, and build around them, inspiring us to create a seamless transition from old to new,” said Elaine Spottswood, founder and principal of Spottswood Interiors. ”Each of the six bedrooms is uniquely appointed, preserving Key West’s signature island-style, and now merged with modern amenities that make it the ideal escape for the discerning traveler.”
The hotel is located in one of the most active and celebrated parts of the city — just down the street from President Harry S Truman’s Winter White House, within walking distance of the Hemingway Home and Museum, and steps from Duval Street.
