Spottswood Companies, Inc.

Passion. Experience. Diligence.

Built upon the foundation of tradition, a company rooted not only in the business of hospitality, but also in the concept.


Founded in 1992, Spottswood Companies, Inc. is in its second decade of active property development. However, the Spottswood family has been deeply involved in Key West real estate, politics, and society for over 150 years. Colonel Walter C. Maloney, Sr., thrice the great grandfather of today's generation, first arrived in the Florida Keys in the 1820's. In 1838, Maloney, Sr. married Mary Elizabeth Rigby, a young woman born in the Bahamas of English ancestry. He went on to serve his community in many capacities, including Clerk of the Court, Mayor, State Legislator, Judge Advocate of the U.S. Naval Courts in Key West, U.S. Marshall, and U.S. Postmaster. In 1876, he wrote the earliest historical account of Key West, "A Sketch of Key West."

John M Spottswood, Sr. with President Harry Truman aboard Spottswood’s PT boat, Ranger.

John M Spottswood, Sr. with President Harry Truman aboard Spottswood’s PT boat, Ranger.

Walter C. Maloney, Jr. was born in Key West in 1839. He became an attorney like his father and followed in his father's footsteps, becoming Mayor and City Attorney. Through the middle and later portions of the 19th century, Walter Jr. published and Walter Sr. edited the local newspaper, The Key West Dispatch. In 1885, Walter, Jr. and several others organized the first street railway system in Key West.

In 1903, the grandson of Walter Sr., Dr. John B. Maloney, founded Key West Drug Company and, in 1908, established the Louise Maloney Hospital, the first private hospital in Key West. In the early 1900's, the great granddaughter of Walter Sr., Florence Maloney, married Colonel Robert F. Spottswood, a direct descendant of Governor Alexander Spottswood, the first Colonial Governor of Virginia. In 1917, Miss Florence, as she was known around town, founded the Key West Chapter of the American Red Cross. Through the mid-1900's Colonel Bob and Miss Florence ran Key West Drug Company, providing medical help and medicines to the people of Key West through some of the island's toughest years.

In 1944, John Maloney Spottswood, Florence's son and the great-great grandson of Walter Sr., founded Key West's first radio station, WKWF, which has been honored frequently over the years for its community service. In 1949, John married Mary Myrtle Sellers. John and Mary were active in business and in local, state, and national politics. In 1955, John established Cable-Vision, Inc., one of the first cable television systems in the country. John served his community as Sheriff for four terms, and State Senator for four terms, and was one of a handful of people who envisioned and established the Florida Sheriff's Youth Ranch.

In the 1960's, John purchased the Casa Marina Hotel and the La Concha Hotel, which initiated the family's involvement in the hotel business. Following John's death, the current Spottswood generation spearheaded the restoration and redevelopment of these two historic properties.

Today, Jack, Bill, Fawni and Robert Spottswood carry on the family's traditions of community service coupled with the responsible development of programs and properties that are in the best interests of all who live, work and visit Key West.



20151117 Comm. Spottswood 01 final.jpg

President/CEO/Director of Spottswood Companies

Robert Spottswood

Robert A. Spottswood was born in Key West, Florida in 1957. Mr. Spottswood graduated from Key West High School in 1975, the University of Florida in 1979 and the University of Miami, School of Law in 1982. A partner in the Miami law firm of Taylor, Brion, Buker & Greene, Mr. Spottswood specialized in corporate law until 1992 when he returned home to Key West to create what would become Spottswood Companies, Inc.

In the two-plus decades since, Spottswood Companies has grown to become one of the leading real estate development, property management and hospitality businesses in the Florida Keys. The company was responsible for the creation of the Hyatt Vacation Club and for the development of numerous timeshare, hotel and commercial properties including Hyatt Sunset Harbor, Hyatt Beach House, Hyatt Windward Pointe Resorts, Key West Marriott Beachside Hotel and Faro Blanco Resort & Yacht Club. The company also provides asset management to the legendary La Concha Hotel, a hotel once owned by the Spottswood family and made famous by luminaries such as Tennessee Williams and Ernest Hemingway.

Mr. Spottswood is President of Spottswood Companies, Inc., a Director of First State Bank, a member of the Florida Council of 100, a member of the Real Estate Roundtable, a member of the Judicial Nominating Commission for the Florida Third District Court of Appeal, Chairman of the Florida Fish and Wildlife Conservation Commission, and Chairman of the American Resort Development Association.

Mr. Spottswood is an attorney, certified public accountant, Chartered Global Management Accountant, and a licensed real estate broker.



Vice President/Director - Spottswood Companies, Inc

Chairman - First State Bank of the Florida Keys

Partner Spottswood, Spottswood, Spottswood & Sterling

John Maloney Spottswood, Jr

John Maloney Spottswood Jr. graduated from Tulane University, B.A Economics in 1972 and from Florida State University Law School in 1975. He is the founder and senior partner at the law firm Spottswood, Spottswood, Spottswood & Sterling; Executive Chairman of the Board of Directors of First State Bank. During his career he has served many boards and civic organizations, including counsel for the Housing Authority of the City of Key West, Assistant City Attorney for the City of Key West, Vice Chairman and Commissioner of the Key West Redevelopment Agency, Vice Chairman and Trustee of the Florida Keys Community College, Co-Chairman for the Commissioning Committee of the USS Key West nuclear submarine, Trustee of the Mitchel Wolfson Family Foundation, Member of the Board of Visitors of The Florida State University Law School, Chairman and Member of the Military Affairs Committee and Commodore of the Key West Yacht Club.



Vice President/Director - Spottswood Companies, Inc.
President of Keystar, Inc.

William B. Spottswood

Mr. Spottswood graduated from the University of Florida with a degree in accounting in 1975 and from the Florida State University Law School in 1977. He is president of Keystar, Inc., a partner in the law firm Spottswood, Spottswood & Spottswood, and a Director of First State Bank of the Florida Keys.

In his capacity as an attorney, Mr. Spottswood oversaw the Development Approval process for the properties owned and operated by Spottswood Management, as well as for other third party projects effected by Environmental Land Use Law.

As President of Keystar, Inc., Mr. Spottswood has successfully assisted clients in obtaining development approvals by local, state, and federal agencies associated with the development of land and water facilities.