Annapolis Vacation Rentals by Owner.Annapolis, Maryland, offers a variety of vacation rentals by owners, including houses, condos, and cottages. You can explore options on platforms like Vrbo, Airbnb, and ByOwner. For instance, Vrbo lists over 730 properties, including houses and cabins, suitable for various group sizes. Before finalizing your reservation, review recent guest feedback to ensure the property meets your expectations. Several properties are equipped with amenities suitable for families, such as multiple bedrooms and outdoor spaces. Annapolis Vacation Rentals by Owner.