The Ballot Brief
Monroe County, Florida

Key West Mayor

Florida › Monroe County › Key West Mayor

Decided at the 2026 primary: Sam Kaufman won the seat

August 18 result: City Commissioner Sam Kaufman won outright with 57.59 percent over incumbent Mayor Danise "Dee Dee" Henriquez, per the Supervisor of Elections' official results; this nonpartisan race will not appear on the November 3 ballot.

Also ran in the primary

Samuel Kaufman

Nonpartisan

Profile
Biography
Sam Kaufman is an attorney and small business owner who has represented Key West as District II city commissioner since 2015 and served as vice mayor from 2018 to 2024, per the Keys News candidate profile. He has lived in Key West for 27 years and chairs the Florida Keys Outreach Coalition, per the same profile.
Top Priorities
  • Repair roads and upgrade stormwater systems
  • Expand water quality testing and prepare for future flooding
  • Advocate for a stronger local hospital with expanded specialty services
Per the campaign site.
Campaign site
Danise "Dee Dee" Henriquez

Nonpartisan

Profile
Biography
Dee Dee Henriquez is the incumbent Mayor of Key West, first elected in 2024, and a lifelong Key West resident, per Keys News. She previously served more than 20 years as Monroe County Tax Collector before being elected mayor, per the same report.
Top Priorities
  • Advance workforce and affordable housing projects, including The Lofts at Bahama Village
  • Invest in infrastructure and resiliency projects
  • Restore transparency at City Hall through community meetings and public forums
Per the local coverage.
Campaign site

Questions about this race

Who is running for Key West Mayor in 2026?

The Key West Mayor race was decided at the 2026 primary - Sam Kaufman won the seat - and does not appear on the November 3, 2026 ballot. 2 candidates were on the primary ballot: Samuel Kaufman and Danise "Dee Dee" Henriquez. Candidate information follows official Monroe County election filings; verify with the official election office linked below.

When is the Key West Mayor election in Florida?

Election Day is Tuesday, November 3, 2026. Registration deadlines, early voting dates and mail ballot rules for Florida are on the Florida election hub at theballotbrief.com.

How do I see my exact Monroe County ballot?

Enter your ZIP code in the lookup at theballotbrief.com for the statewide and congressional races, or a full street address to add the county, city and district contests for that location.

Sources
Verify this race
Candidate roster from official Monroe County Supervisor of Elections filings, last verified 2026-09-12. Bios and priorities carry their attribution inline.
Cross-check with the official Florida election office, or see the full Monroe County sample ballot and your exact ballot by address.