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Mayors of Key West, Florida in the United States have reflected the city's cultural and ethnic heritage including Cuban and openly gay mayors.

1822–1828 — John H. Fleming, Mayor (head of chamber of commerce as well)
1828–1828 — Edgar Macon, Mayor
- A. 1828–1830 — Edgar Macon, President of the Town Council
- B. 1831–1832 — D. C. Pinkham, President of the Town Council
1832–1833 — Oliver O'Hara, Mayor
1833–1834 — Fielding A. Browne
1834–1835 — Adam Gordon
1835–1837 — Fielding A. Browne (2nd Term)
1837–1838 — William A. Whitehead
1838–1839 — Tomaso Saccheti (Socarty)
1839–1840 — Pardon C. Greene^[1]
1840–1841 — Philip J. Fontaine^[1]
1841–1842 — Alexander Patterson
1842–1844 — Philip J. Fontaine (2nd Term)^[1]
1844–1846 — Benjamin Sawyer
1846–1848 — Walter C. Maloney^[1]
1848–1852 — Alexander Patterson (2nd Term)
1852–1853 — Fernando J. Moreno
1853–1854 — John W. Porter
1854–1854 — John W. Porter (2nd Term)
1854–1855 — William Curry
1855–1856 — Philip J. Fontaine (3rd Term)
1856–1857 — Alexander Patterson (3rd Term)
1857–1861 — John P. Baldwin
1861–1861 — William Marvin
1861–1864 — Alexander Patterson (4th Term)
1864–1865 — E. O. Gwynn
1865–1866 — Alexander Patterson (5th Term)
1866–1866 — William Marvin (2nd Term)
1866–1867 — E. O. Gwynn (2nd Term)
1867–1868 — Alexander Patterson (6th Term)
1868–1868 — Henry Mulrennan
1868–1868 — W. S. Allen
1868–1869 — Dr. D. W. Whitehurst
1869–1870 — uncertain
1870–1870 — Henry Mulrennan (2nd Term)
1870–1871 — Joseph B. Browne^[1]
1871–1872 — William D. Cash
1872–1873 — Winer Bethel^[1]
1873–1874 — W. S. Allen (2nd Term)
1874–1875 — E. O. Gwynn (3rd Term)
1875–1876 — Carlos M. de Cespedes^[2]
1876–1880 — Livingston W. Bethel
1880–1881 — Robert Jasper Perry
1881–1882 — E. O. Gwynn (4th Term)
1882–1883 — William McClintock
1883–1885 — R. Alfred Monsalvatage
1885–1886 — James G. Jones
1886–1888 — J. W. V. R. Plummer
1888–1889 — James A. Waddell
1889–1891 — Walter C. Maloney, Jr.
1891–1895 — Robert Jasper Perry (2nd Term)
1895–1897 — James A. Waddell (2nd Term)
1897–1898 — John B. Maloney
1898–1903 — George L. Bartlum
1903–1905 — Benjamin D. Trevor
1905–1907 — George L. Babcock
1907–1915 — Dr. Joseph N. Fogarty
1915–1917 — Norberg Thompson
1917–1919 — Allan B. Cleare
1919–1921 — Louis E. Otto
1921–1925 — Frank H. Ladd
1925–1933 — Leslie A. Curry
1933–1935 — William H. Malone
1935–1937 — Henry C. Galey
1937–1945 — Willard Albury
1945–1945 — William W. Demeritt
1945–1945 — John Carbonell
1945–1947 — William W. Demeritt (2nd Term)
1947–1949 — A. Maitland Adams
1949–1950 — Louis M. J. Eisner
1950–1951 — John Carbonell (2nd Term)
1951–1951 — Louis M. J. Eisner (2nd Term)
1951–1957 — C. B. Harvey
1957–1961 — Delio Cobo
1961–1963 — C. B. Harvey (2nd Term)
1963–1969 — Kermit Lewin
1969–1971 — Delio Cobo (2nd Term)
1971–1981 — Charles "Sonny" McCoy
1981–1983 — Dennis Wardlow^[3]
1983–1985 — Richard A. Heyman
1985–1987 — Tom Sawyer
1987–1989 — Richard A. Heyman (2nd Term)
1989–1989 — John Ingahm
1989–1991 — Tony Tarracino
1991–1995 — Dennis Wardlow (2nd Term)
1995–1995 — Tom Sawyer
1995–1997 — Dennis Wardlow (3rd Term)
1997–1999 — Sheila Mullins
1999–2005 — Jimmy Weekley
2005–2009 — Morgan McPherson
2009–2018 — Craig Cates
2018–present — Teri Johnston

Notes

^ ^a ^b ^c ^d ^e ^f Dates are not proven
^ Carlos Manuel de Céspedes y Céspedes was the son of Carlos Manuel de Céspedes, Cuba's "Father of the Motherland" (Paula Harper. "Cuba Connections: Key West—Tampa—Miami, 1870 to 1945." The Journal of Decorative and Propaganda Arts. Vol. 22. [1996], p.279-80.)
^ Self-styled "Prime Minister" of the Conch Republic, 1982

References

Elected mayors of Key West, as listed in Jefferson B. Browne's Key West: The Old and The New (1912) with additions provided by Monroe County Public Library Historian Tom Hambright, The State Library of Florida, and WorldStatesmen.org.