Get significant tax savings and earn cash flow by investing in a short-term rental with data-backed selection. No guessing!
Find Your Airbnb InvestmentInvesting in Airbnb properties in Portsmouth, Virginia, presents a promising opportunity, driven by its rich naval history, charming waterfront, and proximity to major Hampton Roads attractions. Current market conditions in Portsmouth benefit from consistent tourism, including visitors to the Naval Medical Center Portsmouth, Norfolk Naval Shipyard, and events at the nTelos Wireless Pavilion. Property values in Portsmouth offer a relatively accessible entry point compared to some other coastal Virginia cities, making it an attractive option for investors looking for potentially strong returns. The city's ongoing revitalization efforts, combined with its appeal as a historic destination, suggest a positive investment potential for short-term rentals.
Based on available market data and rental analytics, average Airbnb earnings in Portsmouth, Virginia typically range from $800 to $2,200 per month for standard properties, with waterfront or historic district listings commanding higher rates of $1,500 to $3,500 monthly. Seasonal variations show peak earnings during summer months (June through August) when revenue can increase by 25-40% due to tourism and naval activity, while winter months typically see a 15-20% decrease in bookings and rates. Properties near the Norfolk Naval Shipyard and downtown Portsmouth's entertainment district generally outperform suburban listings by approximately 20-30%, with average daily rates ranging from $65 to $150 depending on property size and amenities. Key factors affecting earnings include proximity to military installations, walkability to restaurants and attractions, parking availability, and property condition, with professionally managed listings typically earning 15-25% more than owner-operated properties. The market benefits from Portsmouth's strategic location within the Hampton Roads metropolitan area, providing steady demand from military personnel, business travelers, and tourists visiting the region's historical sites and waterfront attractions.
Airbnb investments in Portsmouth, Virginia typically generate ROI between 8-12% annually, with properties averaging $85-120 per night and occupancy rates around 65-75% due to the city's proximity to Norfolk Naval Base and downtown Norfolk attractions. The average payback period ranges from 8-12 years depending on initial investment and property type, with waterfront and historic district properties performing better. Compared to traditional long-term rentals yielding 6-8% ROI in Portsmouth's rental market where average rents are $1,200-1,500 monthly, short-term rentals can outperform by 2-4 percentage points, though they require significantly more active management and carry higher vacancy risks. Properties near the Elizabeth River waterfront and within walking distance of Olde Towne Portsmouth tend to achieve the higher end of ROI ranges, while suburban locations typically see more modest returns closer to 8-9% annually.
Portsmouth, Virginia Airbnb properties typically maintain an average occupancy rate of approximately 65-70% annually, with significant seasonal variations that peak during summer months (June through August) at around 80-85% due to the area's proximity to Norfolk Naval Base, Virginia Beach attractions, and favorable weather conditions. Spring and fall months generally see moderate occupancy rates of 60-65%, while winter months drop to approximately 45-55% as tourism declines and military personnel movements decrease. Portsmouth's occupancy rates tend to run slightly below Virginia's statewide average of 68-72% and the national Airbnb average of 70-75%, primarily due to its smaller tourism market compared to more established destinations like Virginia Beach or Richmond, though the city benefits from steady demand from military families, business travelers visiting the Norfolk area, and tourists exploring the historic downtown district and waterfront attractions.
The best Airbnb investment neighborhoods in Portsmouth, Virginia include **Olde Towne**, the historic waterfront district offering premium pricing due to its cobblestone streets, colonial architecture, and proximity to the Elizabeth River, attracting tourists seeking authentic historical experiences. **Park View** provides excellent value with its tree-lined streets, affordable property prices, and proximity to Portsmouth City Park, appealing to families and budget-conscious travelers. **Cradock** offers strong rental potential with its established residential character, reasonable property costs, and easy access to major highways connecting to Norfolk and Virginia Beach attractions. **Port Norfolk** presents waterfront investment opportunities with scenic river views and growing appeal among visitors seeking peaceful retreats near urban amenities. **Churchland** attracts investors due to its suburban family appeal, competitive property prices, and proximity to shopping centers and restaurants. **Cavalier Manor** provides affordable entry points for investors with decent rental demand from military personnel and contractors due to its location near naval facilities. **Brighton** rounds out the top neighborhoods with its residential stability, moderate property values, and accessibility to both Portsmouth attractions and neighboring cities, making it suitable for longer-term stays and business travelers.
Portsmouth, Virginia requires short-term rental operators to obtain a business license and register their property with the city, typically costing between $50-100 annually. Properties must comply with zoning regulations that generally restrict short-term rentals to certain residential districts, with some areas requiring conditional use permits. Occupancy limits are typically set at two persons per bedroom plus two additional guests, with a maximum of 10-12 occupants total depending on the property size. Owner-occupancy requirements vary by zoning district, with some areas mandating that the owner reside on the property as their primary residence for at least 185 days per year, while others allow non-owner-occupied rentals with additional restrictions. The registration process involves submitting an application with property details, proof of insurance, emergency contact information, and passing safety inspections that verify smoke detectors, carbon monoxide detectors, and proper egress routes. Recent changes implemented around 2022-2023 have included stricter enforcement of noise ordinances, mandatory posting of house rules and emergency contacts, parking requirements of one space per bedroom, and enhanced penalties for violations including potential license revocation after multiple infractions.
Short-term rentals in Portsmouth, Virginia are subject to several fees and taxes including the state transient occupancy tax of 5.3% on gross receipts, plus Portsmouth's local lodging tax of approximately 5-7% depending on the specific location within the city. Property owners must obtain a business license costing around $30-50 annually and register for a short-term rental permit with fees typically ranging from $100-200 per year. Additional requirements include Virginia state sales tax of 5.3% on rental income, potential homeowner association fees if applicable, and compliance costs for safety inspections which can range from $75-150 annually. Tourism promotion fees may apply at 1-2% of gross receipts, and some properties may be subject to additional municipal fees for zoning compliance or special use permits costing $200-500 depending on the property type and location within Portsmouth's jurisdiction.
Investing in Airbnb properties in Portsmouth, Virginia, presents a promising opportunity, driven by its rich naval history, charming waterfront, and proximity to major Hampton Roads attractions. Current market conditions in Portsmouth benefit from consistent tourism, including visitors to the Naval Medical Center Portsmouth, Norfolk Naval Shipyard, and events at the nTelos Wireless Pavilion. Property values in Portsmouth offer a relatively accessible entry point compared to some other coastal Virginia cities, making it an attractive option for investors looking for potentially strong returns. The city's ongoing revitalization efforts, combined with its appeal as a historic destination, suggest a positive investment potential for short-term rentals.
Based on available market data and rental analytics, average Airbnb earnings in Portsmouth, Virginia typically range from $800 to $2,200 per month for standard properties, with waterfront or historic district listings commanding higher rates of $1,500 to $3,500 monthly. Seasonal variations show peak earnings during summer months (June through August) when revenue can increase by 25-40% due to tourism and naval activity, while winter months typically see a 15-20% decrease in bookings and rates. Properties near the Norfolk Naval Shipyard and downtown Portsmouth's entertainment district generally outperform suburban listings by approximately 20-30%, with average daily rates ranging from $65 to $150 depending on property size and amenities. Key factors affecting earnings include proximity to military installations, walkability to restaurants and attractions, parking availability, and property condition, with professionally managed listings typically earning 15-25% more than owner-operated properties. The market benefits from Portsmouth's strategic location within the Hampton Roads metropolitan area, providing steady demand from military personnel, business travelers, and tourists visiting the region's historical sites and waterfront attractions.
Airbnb investments in Portsmouth, Virginia typically generate ROI between 8-12% annually, with properties averaging $85-120 per night and occupancy rates around 65-75% due to the city's proximity to Norfolk Naval Base and downtown Norfolk attractions. The average payback period ranges from 8-12 years depending on initial investment and property type, with waterfront and historic district properties performing better. Compared to traditional long-term rentals yielding 6-8% ROI in Portsmouth's rental market where average rents are $1,200-1,500 monthly, short-term rentals can outperform by 2-4 percentage points, though they require significantly more active management and carry higher vacancy risks. Properties near the Elizabeth River waterfront and within walking distance of Olde Towne Portsmouth tend to achieve the higher end of ROI ranges, while suburban locations typically see more modest returns closer to 8-9% annually.
Portsmouth, Virginia Airbnb properties typically maintain an average occupancy rate of approximately 65-70% annually, with significant seasonal variations that peak during summer months (June through August) at around 80-85% due to the area's proximity to Norfolk Naval Base, Virginia Beach attractions, and favorable weather conditions. Spring and fall months generally see moderate occupancy rates of 60-65%, while winter months drop to approximately 45-55% as tourism declines and military personnel movements decrease. Portsmouth's occupancy rates tend to run slightly below Virginia's statewide average of 68-72% and the national Airbnb average of 70-75%, primarily due to its smaller tourism market compared to more established destinations like Virginia Beach or Richmond, though the city benefits from steady demand from military families, business travelers visiting the Norfolk area, and tourists exploring the historic downtown district and waterfront attractions.
The best Airbnb investment neighborhoods in Portsmouth, Virginia include **Olde Towne**, the historic waterfront district offering premium pricing due to its cobblestone streets, colonial architecture, and proximity to the Elizabeth River, attracting tourists seeking authentic historical experiences. **Park View** provides excellent value with its tree-lined streets, affordable property prices, and proximity to Portsmouth City Park, appealing to families and budget-conscious travelers. **Cradock** offers strong rental potential with its established residential character, reasonable property costs, and easy access to major highways connecting to Norfolk and Virginia Beach attractions. **Port Norfolk** presents waterfront investment opportunities with scenic river views and growing appeal among visitors seeking peaceful retreats near urban amenities. **Churchland** attracts investors due to its suburban family appeal, competitive property prices, and proximity to shopping centers and restaurants. **Cavalier Manor** provides affordable entry points for investors with decent rental demand from military personnel and contractors due to its location near naval facilities. **Brighton** rounds out the top neighborhoods with its residential stability, moderate property values, and accessibility to both Portsmouth attractions and neighboring cities, making it suitable for longer-term stays and business travelers.
Portsmouth, Virginia requires short-term rental operators to obtain a business license and register their property with the city, typically costing between $50-100 annually. Properties must comply with zoning regulations that generally restrict short-term rentals to certain residential districts, with some areas requiring conditional use permits. Occupancy limits are typically set at two persons per bedroom plus two additional guests, with a maximum of 10-12 occupants total depending on the property size. Owner-occupancy requirements vary by zoning district, with some areas mandating that the owner reside on the property as their primary residence for at least 185 days per year, while others allow non-owner-occupied rentals with additional restrictions. The registration process involves submitting an application with property details, proof of insurance, emergency contact information, and passing safety inspections that verify smoke detectors, carbon monoxide detectors, and proper egress routes. Recent changes implemented around 2022-2023 have included stricter enforcement of noise ordinances, mandatory posting of house rules and emergency contacts, parking requirements of one space per bedroom, and enhanced penalties for violations including potential license revocation after multiple infractions.
Short-term rentals in Portsmouth, Virginia are subject to several fees and taxes including the state transient occupancy tax of 5.3% on gross receipts, plus Portsmouth's local lodging tax of approximately 5-7% depending on the specific location within the city. Property owners must obtain a business license costing around $30-50 annually and register for a short-term rental permit with fees typically ranging from $100-200 per year. Additional requirements include Virginia state sales tax of 5.3% on rental income, potential homeowner association fees if applicable, and compliance costs for safety inspections which can range from $75-150 annually. Tourism promotion fees may apply at 1-2% of gross receipts, and some properties may be subject to additional municipal fees for zoning compliance or special use permits costing $200-500 depending on the property type and location within Portsmouth's jurisdiction.
* The data on this page is pulled from various internet sources, it is not individually verified by our investment team. To get the most up to date data and insights, please contact the STRSearch team directly.
How Smart Investors Build Wealth
Through Data-Driven STRs (Real Results)
From first-time investors to seasoned pros, see how our commitment to comprehensive data analysis led to unparalleled investment victories.
From zero real estate experience to a thriving short-term rental business, Allison locked in $120K in revenue her first year and is now expanding with STR Search again. Proof that the right team can turn analysis paralysis into profitable action!

Thanks to John's expert guidance, I made my first real estate and Airbnb investment a massive success, with consistent positive cash flow and an exceptional return on investment!

John's training gave me the confidence to secure a loan on the spot and scale from one STR to three. His approach is a total game-changer!
Why Choose STR Search?

Put your money to work & lower your tax bill
We’ve spent years analyzing what works so you don’t have to. Our job is to cut through bad data and help you make smart, profitable decisions backed by real numbers.
Schedule Your Free CallTrusted by hundreds of successful investors
Generate $3-5K+ monthly cash flow with our proven property matching system.
Build long-term wealth through STRs with cash flow, equity, and bonus depreciation.
Skip 6-12 months of trial and error with our data-driven underwriting and market analysis
We have a 100% success rate across $90M+ in Real Estate
Out of the 200+ properties we've helped our clients buy every single one has been profitable.
You want more money. More time. More freedom. But may be stuck trading hours for dollars, and scaling your investment strategy feels out of reach.
While others are getting lost in analysis paralysis, you’ve got capital and drive to change your situation. Investors who choose the right STRs can generate $3–5K/month in cash flow, plus serious tax benefits and long-term wealth.
We’ve spent years obsessed with STR investing data so you don’t have to.
With our property match services, there’s no guesswork! Just profitable properties built to perform. With the right deal, your capital can buy more than returns. It can buy your freedom.





All The Ways We Can Help You
Free courses, services, and trainings, to help you maximize your earnings from AirBnb...
Get in touch with us.

Everything Smart Investors Ask About STR Wealth Building
To start an Airbnb in Portsmouth, Virginia, begin by researching local zoning laws and regulations through the Portsmouth Planning Department, as the city requires short-term rental operators to obtain a business license and may have specific zoning restrictions in residential areas. Contact Portsmouth's Department of Permits and Inspections to secure necessary permits, including a business license (approximately $30-50 annually) and potentially a special use permit depending on your property's zoning classification. Find a suitable property by searching areas like Olde Towne Portsmouth or neighborhoods near the Norfolk Naval Shipyard, ensuring the property meets safety requirements including smoke detectors, carbon monoxide detectors, and proper egress windows. Furnish the space with essential amenities including quality bedding, kitchen supplies, WiFi, and local guidebooks highlighting Portsmouth's historic attractions and proximity to Norfolk. Create your Airbnb listing with professional photos showcasing the property's proximity to the Elizabeth River waterfront and historic downtown area, setting competitive rates based on similar properties in the Hampton Roads region (typically $75-150 per night). Manage your property by establishing check-in procedures, maintaining cleanliness standards, responding promptly to guest inquiries, and ensuring compliance with Virginia's 5.3% state sales tax and Portsmouth's local occupancy tax requirements, while keeping detailed records for tax purposes and regularly monitoring local regulation changes through the city's official website and planning department updates.
To identify profitable short-term rental properties in Portsmouth, Virginia, focus on locations within 1-2 miles of the Norfolk Naval Shipyard, downtown Portsmouth's historic district near High Street, and waterfront areas along the Elizabeth River for their proximity to major employers and tourist attractions. Target 2-4 bedroom properties built after 1980 with dedicated parking, updated kitchens and bathrooms, outdoor spaces, and strong WiFi infrastructure, as these features command premium rates from military personnel, business travelers, and tourists visiting the Hampton Roads region. Conduct pricing analysis using AirDNA and Mashvisor to benchmark against comparable properties, aiming for average daily rates of $80-150 depending on size and location, with occupancy rates of 65-75% being realistic in this market. Research competition by analyzing existing Airbnb and VRBO listings within a 3-mile radius, noting their pricing strategies, amenities, and guest reviews to identify market gaps and positioning opportunities. Utilize tools like Rabbu, BiggerPockets calculators, and local MLS data through Virginia Beach-Norfolk Association of Realtors, while connecting with Portsmouth Economic Development and local property management companies like Awning or RedAwning who understand the unique dynamics of military housing allowances and corporate travel patterns that drive demand in this Hampton Roads submarket.
To obtain an Airbnb/STR permit in Portsmouth, Virginia, you must first contact the Portsmouth Department of Economic Development or the Planning Department at City Hall located at 801 Crawford Street to determine specific zoning compliance for short-term rentals, as regulations vary by district. Submit an application that typically includes a completed STR permit form, proof of property ownership or lease agreement with landlord consent, certificate of occupancy, business license application, liability insurance documentation showing minimum $1 million coverage, floor plan of the rental unit, and contact information for a local property manager if you're not residing locally. The application fee ranges from $150-300 annually, with additional business license fees of approximately $50-100. You'll need to schedule and pass safety inspections covering fire safety, electrical systems, and occupancy limits, which may take 2-4 weeks to complete. The entire approval process typically takes 4-8 weeks from submission to permit issuance. Portsmouth requires STR operators to maintain guest registries, limit occupancy to posted maximums, provide 24-hour contact information to neighbors, ensure adequate parking, and comply with noise ordinances, with some residential zones having restrictions on the number of rental days per year or requiring conditional use permits for properties not owner-occupied.
Short-term rentals (STRs) are legal in Portsmouth, Virginia, but operate under specific regulations established by the city. Portsmouth requires STR operators to obtain a business license and comply with zoning restrictions that generally limit short-term rentals to certain residential districts while prohibiting them in some historic or densely populated neighborhoods. The city typically requires a minimum rental period of 3-7 days and mandates that properties meet safety standards including smoke detectors, carbon monoxide detectors, and fire extinguishers. Operators must also collect and remit local lodging taxes, maintain liability insurance, and provide emergency contact information to the city and neighbors. Portsmouth has implemented occupancy limits based on property size and parking requirements, while also establishing noise ordinances and guest behavior standards to address neighborhood concerns. Recent changes around 2020-2022 included stricter enforcement mechanisms and increased penalties for violations, with the city requiring annual license renewals and conducting periodic inspections to ensure compliance with health, safety, and zoning requirements.
The best Airbnb investment areas in Portsmouth, Virginia include the Olde Towne Historic District, which attracts tourists with its colonial architecture, antique shops, and proximity to the Elizabeth River waterfront, generating strong weekend and holiday bookings. The Port Norfolk neighborhood offers excellent value with its historic homes and easy access to downtown Norfolk via the Elizabeth River Ferry, appealing to business travelers and tourists visiting the Norfolk Botanical Garden. The Cradock area provides affordable investment opportunities while serving military personnel from Norfolk Naval Shipyard and nearby bases, ensuring consistent occupancy year-round. The Churchland district benefits from its proximity to the Portsmouth Naval Medical Center and offers good rental potential for medical professionals and military families on temporary assignments. Finally, the waterfront areas near High Street Landing and the Elizabeth River Trail attract visitors interested in maritime activities, festivals, and events at the Portsmouth Art & Cultural Center, with properties here commanding premium rates during summer months and special events like the Seawall Festival.
In Portsmouth, Virginia, Airbnb hosts are subject to both state and local lodging taxes. The Virginia state transient occupancy tax is 5.3% and applies to stays of less than 30 consecutive days. Portsmouth imposes an additional local transient occupancy tax of 5% on short-term rental accommodations. These taxes are typically collected by Airbnb directly from guests at the time of booking and remitted to the appropriate tax authorities on behalf of hosts through Airbnb's automatic tax collection service, which began around 2019-2020 for Virginia localities. Hosts may still need to register with the Virginia Department of Taxation and Portsmouth's tax office to ensure compliance and may be required to file periodic returns even when Airbnb collects the taxes. Stays of 30 days or longer are generally exempt from transient occupancy taxes, and certain government employees or military personnel may qualify for exemptions under specific circumstances. The combined effective tax rate for short-term stays is approximately 10.3%, and hosts should verify their registration requirements with both state and local tax authorities regardless of Airbnb's collection services.
Starting an Airbnb in Portsmouth, Virginia requires approximately $285,000-$320,000 in total initial investment. Property purchase costs average $180,000-$200,000 based on median home prices in Portsmouth as of 2023. Furnishing a 2-3 bedroom property typically runs $15,000-$25,000 including furniture, appliances, linens, and décor from retailers like IKEA, Wayfair, and local suppliers. Initial setup costs including professional photography, listing creation, and marketing materials total $2,000-$3,500. Permits and fees vary but expect $500-$1,200 for business licenses, short-term rental permits, and city registration requirements. Insurance premiums for short-term rental coverage average $2,400-$3,600 annually, with companies like Proper Insurance and CBIZ providing specialized Airbnb policies. Utility deposits and setup fees for electricity, water, gas, internet, and cable total $800-$1,500. First six months of operating costs including utilities ($900/month), cleaning services ($100-150 per turnover), supplies and maintenance ($300/month), platform fees to Airbnb (3% of bookings), and property management software subscriptions total approximately $8,000-$12,000, assuming 60-70% occupancy rates typical for Portsmouth's tourism market.
Airbnb properties in Portsmouth, Virginia typically generate average monthly revenues of $1,800-$2,400 for entire homes and $800-$1,200 for private rooms, with annual occupancy rates ranging from 55-70% according to 2023 market data from AirDNA and Mashvisor. Operating expenses generally consume 40-50% of gross revenue, including cleaning fees ($75-$125 per turnover), property management (15-25% of revenue), utilities ($150-$250 monthly), insurance ($1,200-$2,000 annually), and maintenance costs averaging $200-$400 monthly. Properties near the Norfolk Naval Shipyard and downtown Portsmouth waterfront command premium rates of $120-$180 nightly compared to suburban locations at $80-$120, with successful hosts like those operating converted historic homes on High Street reporting net profit margins of 25-35% after all expenses. Key success factors include proximity to military installations, professional photography, consistent 4.8+ star ratings, and strategic pricing during peak summer months and military graduation periods, with the most profitable properties being 2-3 bedroom homes purchased below $200,000 that can achieve 12-18% annual returns on investment when properly managed and marketed to business travelers and military families.
Airbnb investments in Portsmouth, Virginia typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% based on current market conditions. Properties near the Norfolk Naval Shipyard and downtown Portsmouth historic district command premium rates of $80-120 per night, with occupancy rates averaging 65-75% annually. Initial investment recovery typically occurs within 7-10 years, with monthly gross rental income of $1,800-2,800 for a standard 2-3 bedroom property purchased at Portsmouth's median home price of $180,000-220,000. Operating expenses including property management, utilities, maintenance, and Airbnb fees typically consume 40-50% of gross revenue, leaving net annual returns of $8,000-15,000 depending on property location and amenities. Properties within walking distance of the Portsmouth waterfront and ferry terminal to Norfolk achieve faster profitability timelines of 6-8 years due to higher nightly rates and consistent business traveler demand from the military and shipyard operations.
STRSearch leads the national market for Airbnb investment property analysis and market research tools for Portsmouth, Virginia. Local real estate agents specializing in short-term rental investments include Keller Williams Realty agents like Sarah Mitchell and The Liz Moore Company's vacation rental specialists who focus on the Portsmouth waterfront and historic districts. National services include Awning (formerly RedAwning) which provides full-service Airbnb property management and investment guidance, Mashvisor for property analytics and market data, AirDNA for revenue projections and market insights, and Roofstock which offers turnkey rental properties including STR-suitable homes. Local Portsmouth companies include Tidewater Property Management Group and Hampton Roads Vacation Rentals who assist with both acquisition and management services. Additional national platforms like BiggerPockets connects investors with local Portsmouth agents experienced in Airbnb properties, while HostGPO provides purchasing power for furnishing and setting up profitable short-term rentals in the Portsmouth market, particularly targeting properties near the Norfolk Naval Shipyard and downtown Portsmouth's entertainment district.

We match people with amazing properties
The Formula Works. Years of passionate data analysis have perfected our formula, making it a beacon of accuracy in real estate investments. Trust in precision that turns data into profit.
Schedule Your Free CallMaximize Your Returns with Smart Tax Strategies
Unlock the full potential of your short-term rental investments with our tailored tax strategy. We ensure your properties not only cash flow but also leverage tax benefits to boost your bottom line. Let us navigate the complexities, so you can enjoy the rewards.
Schedule Your Free Call

Short-Term Rentals are alive and well
No other company matches our expansive collection of properties or our unwavering success streak over the last two years. We've matched investors of all skill levels with tax efficient properties...
Schedule Your Free CallWe're Trusted By the Best in the Business
STR Search and the Bianchi Method has gained a reputation among industry leaders as being the front runner in consistently matching people with profitable properties.





Put your money to work & lower your tax bill
We’ve spent years analyzing what works so you don’t have to. Our job is to cut through bad data and help you make smart, profitable decisions backed by real numbers.
Schedule Your Free Call




