Performance indicators for the Annapolis short-term rental market based on reliable data.
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Reliable / Active
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Middle-Earners Gross Yield
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Middle-Earners Revenue
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Middle-Earners Occupancy
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Median Home Sale Price
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Top-Earners Revenue
The highest-performing listings in Annapolis.
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Challenging to Investors
Annapolis allows STRs but imposes a strict 10% blockface cap with a lottery, limiting supply in high-demand areas. Licensing is multi-step (state tax ID, CSS portal registration, local contact for non-residents) and requires ongoing reporting plus an 8% occupancy tax. Enforcement is inconsistent, with only ~50% of listed properties licensed, raising compliance risk and limiting investment certainty.
Local STR Agent
STR specialist · Annapolis, MD
Annapolis, the capital of Maryland, is a city steeped in rich history and nautical charm. With a population of approximately 40,000 residents, Annapolis is located about 33 miles east of Washington, D.C. Its prime location along the Chesapeake Bay makes it a desirable destination for tourists and short-term rental seekers alike.
Prominent landmarks in Annapolis include the United States Naval Academy, a prestigious institution offering stunning grounds and historical significance. For more information, you can visit their official website: United States Naval Academy. Another key attraction is the Maryland State House, the oldest U.S. state capitol still in continuous legislative use, which can be explored further at: Maryland State House.
Annapolis is also known for its well-preserved Colonial architecture, vibrant waterfront, and numerous sailing and boating activities. The downtown harbor area provides picturesque views and is a hub for dining, shopping, and cultural events, ideal for visitors looking for a versatile and engaging stay.