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The highest-performing listings in Portsmouth.
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Generally Investor friendly
Owner‑occupied STRs are permitted by state law with no local license/caps yet and only a modest 1% local tax plus 5.3% state sales tax; planning for the upcoming ordinance introduces compliance and cost risk but remains manageable.
Local STR Agent
STR specialist · Portsmouth, VA
Portsmouth, Virginia is an independent city in the Commonwealth of Virginia, situated on the western shore of the Elizabeth River opposite Norfolk. With a population of approximately 95,000, it forms part of the densely settled Hampton Roads metropolitan area along the southeastern Virginia coast. The city carries a working-maritime character shaped by centuries of naval shipbuilding, layered with a leafy 18th- and 19th-century historic core, a walkable riverfront, and a growing arts and dining scene. It is best known as a gateway to the broader Hampton Roads region, including Virginia Beach, the colonial-era sites of the Historic Triangle, and the Atlantic beaches of the Delmarva Peninsula. Portsmouth lies about 20 miles west of Virginia Beach and roughly 90 miles southeast of Richmond, just across the river from downtown Norfolk.
Olde Towne Historic District sits at the heart of Portsmouth and is widely recognized as one of the largest collections of historically significant homes between Alexandria, Virginia and Charleston, South Carolina. The walkable neighborhood features Federal-, Georgian-, and Victorian-era residences, a number of historic churches, and a centuries-old cemetery. It is essentially within Portsmouth itself, just a short walk from the downtown waterfront and a short drive from the city's ferry terminal.
The Norfolk Naval Shipyard, locally referred to as the Portsmouth Naval Shipyard, is one of the oldest continuously operating shipyards in the country, established in 1767. The working yard is not generally open to visitors, but the adjacent Naval Shipyard Museum interprets more than two centuries of naval construction, including the yard's role in every major American conflict from the Revolutionary War forward. It is only a few minutes from Olde Towne.
The Children's Museum of Virginia, located within the Olde Towne district, is one of the largest children's museums in the state, with hands-on exhibits spanning science, engineering, and Tidewater regional history. The museum draws families from across Hampton Roads and is an easy stop for visitors traveling with younger children.
About an hour northwest of Portsmouth, Colonial Williamsburg anchors the Historic Triangle together with Jamestown and Yorktown, offering a reconstructed 18th-century town, living-history interpreters, and extensive grounds. Closer to home, the downtown districts of Norfolk, the Virginia Beach oceanfront, and First Landing State Park are all within roughly a 30-minute drive, giving visitors a wide radius of beaches, museums, and military history from a single base.
Portsmouth appeals to short-term rental investors because it offers the historic character and waterfront of the larger Hampton Roads cities at a more accessible price point, while remaining within easy reach of the region's most popular draws. The combination of an intact historic core, naval heritage tourism, family-friendly museums, and quick access to the Atlantic beaches and colonial sites makes it a flexible home base for travelers exploring southeastern Virginia.