Airbnb Properties for Sale in Annapolis, MD

Looking for a vacation rental investment in Annapolis, MD with high ROI ?

Explore a range of newly added short-term rental homes in Annapolis, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Annapolis, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1164 Latrobe Dr Annapolis, MD Get ready for a great summer in this great location! New Kitchen w/ SS appliances, granite...	4 beds \| 2 baths \| 1,926 sq.ft.	$525,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.85% Airbnb Rental Income: $3333 Traditional Rental Income: $2369 Airbnb ROI: 3.29% Traditional ROI: 2.85%
1178 Glenwood Dl Annapolis, MD Tucked away on a gorgeous, private lot in the highly sought-after Cape St. Claire communit...	4 beds \| 2 baths \| 1,828 sq.ft.	$550,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 2.63% Airbnb Rental Income: $3333 Traditional Rental Income: $2512 Airbnb ROI: 2.78% Traditional ROI: 2.63%
220 West St Annapolis, MD Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached pr...	3 beds \| 2 baths \| 1,540 sq.ft.	$849,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 0.71% Airbnb Rental Income: $2689 Traditional Rental Income: $2023 Airbnb ROI: 0.75% Traditional ROI: 0.71%
105 Rosecrest Dr Annapolis, MD Fully Renovated Rancher in a Highly Desired Neighborhood! Welcome to this beautifully reno...	4 beds \| 2 baths \| 1,800 sq.ft.	$435,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 2.35% Airbnb Rental Income: $3333 Traditional Rental Income: $1958 Airbnb ROI: 3.77% Traditional ROI: 2.35%
1005 Hyde Park Dr Annapolis, MD Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering clas...	2 beds \| 1 baths \| 1,190 sq.ft.	$489,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 0.73% Airbnb Rental Income: $1908 Traditional Rental Income: $1328 Airbnb ROI: 0.89% Traditional ROI: 0.73%
1041 CEDAR RIDGE Court Annapolis, MD Welcome home to 1041 Cedar Ridge Ct, a well-maintained property offering comfort, convenie...	3 beds \| 3 baths \| 1,320 sq.ft.	$338,200	Airbnb cash on cash: 3.02% Traditional cash on cash: 2.87% Airbnb Rental Income: $2689 Traditional Rental Income: $2005 Airbnb ROI: 3.02% Traditional ROI: 2.87%
3 Cypress Rd Annapolis, MD Nestled in the heart of Annapolis, this 3-bedroom, 1-bath home offers a fantastic opportun...	3 beds \| 1 baths \| 1,206 sq.ft.	$350,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 2.8% Airbnb Rental Income: $2689 Traditional Rental Income: $1762 Airbnb ROI: 3.68% Traditional ROI: 2.8%
1531 Hickory Wood Dr Annapolis, MD 1531 Hickory Wood Dr, Annapolis, MD 21409 \| Single Family Residential	3 beds \| 2 baths \| 916 sq.ft.	$379,900	Airbnb cash on cash: 3.07% Traditional cash on cash: 2.77% Airbnb Rental Income: $2689 Traditional Rental Income: $1940 Airbnb ROI: 3.07% Traditional ROI: 2.77%
LOT 6 Gilmer St Annapolis, MD LOT 6 Gilmer St, Annapolis, MD 21401 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.84% Airbnb Rental Income: $1371 Traditional Rental Income: $758 Airbnb ROI: 6.87% Traditional ROI: 4.84%
1470 Log Inn Rd Annapolis, MD Beautifully updated and filled with thoughtful improvements, this Cape Cod in Annapolis co...	3 beds \| 2 baths \| 1,465 sq.ft.	$535,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.45% Airbnb Rental Income: $2689 Traditional Rental Income: $1691 Airbnb ROI: 2.17% Traditional ROI: 1.45%
1469 Pleasant Lake Rd Annapolis, MD 1469 Pleasant Lake Rd, Annapolis, MD 21409 \| Single Family Residential	4 beds \| 2 baths \| 2,542 sq.ft.	$890,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 0.75% Airbnb Rental Income: $3333 Traditional Rental Income: $2463 Airbnb ROI: 0.9% Traditional ROI: 0.75%
1354 MOYER RD Annapolis, MD Welcome to 1354 Moyer Road, a fantastic opportunity to create your dream home in one of An...	4 beds \| 2 baths \| N/A	$470,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.66% Airbnb Rental Income: $3333 Traditional Rental Income: $2223 Airbnb ROI: 3.49% Traditional ROI: 2.66%
700 N Holly Dr Annapolis, MD Don't miss this rarely available 4-bedroom, 2.5-bath Colonial in the highly sought-after, ...	4 beds \| 2 baths \| 2,072 sq.ft.	$975,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.14% Airbnb Rental Income: $3333 Traditional Rental Income: $2383 Airbnb ROI: 0.36% Traditional ROI: 0.14%
410 WALNUT Drive Annapolis, MD A CHERISHED FAMILY CLASSIC IN WATERFRONT HILLSMERE ESTATES! This home qualifies for zero d...	3 beds \| 1 baths \| 1,368 sq.ft.	$439,990	Airbnb cash on cash: 2.74% Traditional cash on cash: 2.03% Airbnb Rental Income: $2689 Traditional Rental Income: $1760 Airbnb ROI: 2.74% Traditional ROI: 2.03%
100 Oak Dr Annapolis, MD Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-b...	4 beds \| 3 baths \| 2,229 sq.ft.	$749,900	Airbnb cash on cash: 1.6% Traditional cash on cash: 1.38% Airbnb Rental Income: $3333 Traditional Rental Income: $2429 Airbnb ROI: 1.6% Traditional ROI: 1.38%
318 Beach Dr Annapolis, MD 318 Beach Dr, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 2 baths \| 2,738 sq.ft.	$500,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.66% Airbnb Rental Income: $3333 Traditional Rental Income: $2568 Airbnb ROI: 2.7% Traditional ROI: 2.66%
3354 Arundel On The Bay Rd Annapolis, MD 3354 Arundel On The Bay Rd, Annapolis, MD 21403 \| Other	N/A beds \| N/A baths \| N/A	$253,500	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.16% Airbnb Rental Income: $1371 Traditional Rental Income: $869 Airbnb ROI: 1.52% Traditional ROI: 1.16%
208 Parker Ave Annapolis, MD AUCTION Occupied property and inspections NOT available - sold as-is. No for sale sign. Co...	3 beds \| 1 baths \| 1,296 sq.ft.	$385,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 2.58% Airbnb Rental Income: $2689 Traditional Rental Income: $1775 Airbnb ROI: 3.34% Traditional ROI: 2.58%

Vacation Rentals in Annapolis

There are 35 vacation rental properties available for sale in the city of Annapolis . The median list price of Airbnb properties available for sale in Annapolis is $597,392 and the average price per square foot is $233. The cash on cash return on vacation rentals in Annapolis is N/A%. The average monthly short term rental income in Annapolis is $2,481.

Annapolis, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 35 Airbnb properties available for sale in Annapolis.

In 2026, the best neighborhood to buy short term rental property is Annapolis.

In October 2026, the average Airbnb occupancy rate in Annapolis is 22%.

Airbnb data on vacation rentals in Annapolis, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Annapolis, MD market insights, guest information and booking details, seasonality trends and historical Annapolis, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Annapolis, MD

1164 Latrobe Dr

Annapolis, MD

4 beds | 2 baths | 1,926 sq.ft.

$525,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $3333

Traditional Rental Income: $2369

Airbnb ROI: 3.29%

Traditional ROI: 2.85%

1178 Glenwood Dl

Annapolis, MD

4 beds | 2 baths | 1,828 sq.ft.

$550,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $3333

Traditional Rental Income: $2512

Airbnb ROI: 2.78%

Traditional ROI: 2.63%

220 West St

Annapolis, MD

3 beds | 2 baths | 1,540 sq.ft.

$849,900

Airbnb cash on cash: 0.75%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $2689

Traditional Rental Income: $2023

Airbnb ROI: 0.75%

Traditional ROI: 0.71%

105 Rosecrest Dr

Annapolis, MD

4 beds | 2 baths | 1,800 sq.ft.

$435,000

Airbnb cash on cash: 3.77%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $3333

Traditional Rental Income: $1958

Airbnb ROI: 3.77%

Traditional ROI: 2.35%

1005 Hyde Park Dr

Annapolis, MD

2 beds | 1 baths | 1,190 sq.ft.

$489,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $1908

Traditional Rental Income: $1328

Airbnb ROI: 0.89%

Traditional ROI: 0.73%

1041 CEDAR RIDGE Court

Annapolis, MD

3 beds | 3 baths | 1,320 sq.ft.

$338,200

Airbnb cash on cash: 3.02%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2689

Traditional Rental Income: $2005

Airbnb ROI: 3.02%

Traditional ROI: 2.87%

3 Cypress Rd

Annapolis, MD

3 beds | 1 baths | 1,206 sq.ft.

$350,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $2689

Traditional Rental Income: $1762

Airbnb ROI: 3.68%

Traditional ROI: 2.8%

1531 Hickory Wood Dr

Annapolis, MD

3 beds | 2 baths | 916 sq.ft.

$379,900

Airbnb cash on cash: 3.07%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2689

Traditional Rental Income: $1940

Airbnb ROI: 3.07%