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Leonardtown, MD
Generally Investor Friendly
Local STR Agent

YES, short-term rentals are permitted in Leonardtown, MD, subject to specific licensing requirements and regulatory compliance. As the county seat of St. Mary's County, Leonardtown operates under the county's comprehensive zoning framework while requiring additional local permits for short-term rental operations.
Starting a short-term rental business in Leonardtown requires a systematic approach to ensure full compliance with local regulations:
St. Mary's County Department of Planning and Zoning
St. Mary's County Finance Department
Maryland Comptroller
St. Mary's County Health Department
St. Mary's County Board of Appeals
St. Mary's County Public Accommodations Tax Information
St. Mary's County Comprehensive Zoning Ordinance
Local Market and Licensing Information
Disclaimer: This guide is based on information available as of 2025. Regulations may change, and investors should verify current requirements with local authorities before making investment decisions.




Leonardtown is a town in and the county seat of St. Mary's County, Maryland, United States. The population was 4,563 at the 2020 census. Historic Leonardtown includes both a large public high school and a public middle school Leonardtown Middle School as well as a Catholic high school and an elementary school Leonardtown Elementary School, offices of the county government, and St. Mary's Hospital which serves the healthcare needs of the county. The College of Southern Maryland maintains a growing satellite campus within city limits, including an aquatic center. An upscale home development located in the Breton Bay area is just outside town, notable for both its country club golf course and swimming pool. Leonardtown's population has grown significantly since 1990 as a result of the town's proximity to Patuxent River Naval Air Station and the Washington metro area.
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