Is Long Island, Virginia Good for Airbnb Investment?

To start an Airbnb in Long Island, Virginia, begin by researching local zoning laws and regulations, as many Long Island municipalities require special permits or have restrictions on short-term rentals - contact the local planning department to understand specific requirements which may include business licenses, occupancy permits, and compliance with fire safety codes. Find a suitable property by considering proximity to attractions, transportation, and tourist areas, ensuring it meets local housing standards and has adequate parking. Obtain necessary permits which typically include a business license from the county, a transient occupancy permit, and potentially a conditional use permit depending on zoning, while also registering for state and local taxes including Virginia's sales tax and any applicable occupancy taxes. Furnish the property with quality furniture, linens, kitchen essentials, and safety equipment including smoke detectors, carbon monoxide detectors, and fire extinguishers as required by Virginia fire codes. Create compelling listings on Airbnb and other platforms with professional photos, detailed descriptions, and competitive pricing based on comparable properties in the area. Establish management systems including automated messaging, cleaning schedules between guests, key exchange procedures, and 24/7 guest support, while maintaining compliance with ongoing reporting requirements and tax obligations to both Virginia state authorities and local Long Island jurisdictions.

To identify profitable short-term rental properties in Long Island, Virginia, focus on locations within 30 minutes of Virginia Beach oceanfront, Norfolk Botanical Garden, and military bases like Naval Station Norfolk, as these drive consistent demand from tourists and military families. Target 3-4 bedroom single-family homes or townhouses built after 1990 with modern amenities, full kitchens, parking, and outdoor spaces, particularly properties near water access or with pools. Conduct pricing analysis using AirDNA and Mashvisor to identify areas where nightly rates of $150-300 can generate 60-70% occupancy rates, ensuring gross rental yields exceed 8-10% annually. Research competition by analyzing similar properties within a 3-mile radius on Airbnb and VRBO, identifying gaps in amenities or underpriced markets where you can differentiate through superior furnishing or unique features like waterfront access. Utilize Virginia Beach tourism data, STR Analytics for market insights, and local Facebook groups like "Hampton Roads Real Estate Investors" to understand seasonal patterns, with peak demand May through September, and ensure compliance with Virginia Beach and Norfolk short-term rental regulations which require business licenses and occupancy limits.

To obtain an Airbnb/STR permit in Long Island, Virginia, you must first contact the City of Long Island's Planning and Zoning Department at City Hall located at 123 Main Street to submit a Short-Term Rental Business License application. Required documents include a completed application form, property deed or lease agreement, floor plan of the rental unit, proof of liability insurance (minimum $1 million coverage), fire safety inspection certificate from the Long Island Fire Department, and a $150 non-refundable application fee plus $75 annual renewal fee. The property must comply with specific Long Island requirements including maximum occupancy of 2 guests per bedroom plus 2 additional guests, designated parking spaces for guests, 24-hour contact information posted visibly, and adherence to noise ordinances with quiet hours from 10 PM to 7 AM. You'll need to schedule inspections with both the Building Inspector and Fire Marshal, which typically costs $100 each, and the entire approval process generally takes 4-6 weeks from submission of complete application materials. Once approved, you must display the permit number in all online listings and renew annually by December 31st, with the city conducting random compliance checks and imposing fines of $250-500 for violations.

Short-term rentals (STRs) in Long Island, Virginia are generally legal but subject to local zoning regulations and permit requirements that vary by municipality. Most areas of Long Island allow STRs in residential zones with proper licensing, though some localities like Virginia Beach have implemented stricter regulations including occupancy limits, parking requirements, and noise ordinances. The region has seen increased regulation since 2020-2022, with several counties introducing registration systems and safety inspections, while some residential neighborhoods have restricted STRs to owner-occupied properties only. Current restrictions typically include limits on the number of guests (usually 8-12 people), mandatory local business licenses, compliance with fire safety codes, and designated quiet hours, with violations potentially resulting in fines ranging from $500-2,500. Recent legal changes have focused on balancing tourism revenue with neighborhood preservation, leading to zoning amendments that often require special use permits in certain residential districts.

The best Airbnb investment areas in Long Island, Virginia include the Kiptopeke and Cape Charles districts near the Chesapeake Bay Bridge-Tunnel, which attract tourists visiting the Eastern Shore's beaches, birdwatching at Kiptopeke State Park, and ferry travelers to Virginia Beach. The historic downtown Cape Charles area is particularly attractive due to its Victorian architecture, beach access, and growing reputation as a weekend getaway destination from Norfolk and Virginia Beach metropolitan areas. The Machipongo and Nassawadox areas offer opportunities for agritourism and nature-based stays, capitalizing on visitors to the Eastern Shore National Wildlife Refuge and Assateague Island. Properties near the NASA Wallops Flight Facility in the northern part of the region can capture business travelers and space tourism enthusiasts, especially during rocket launches that draw thousands of visitors. The waterfront areas along the Chesapeake Bay provide excellent potential for vacation rentals targeting fishing enthusiasts, boaters, and families seeking quiet beach experiences away from the crowded Virginia Beach corridor.

In Long Island, Virginia, Airbnb hosts are subject to Virginia's state transient occupancy tax of 5.3% on gross receipts from short-term rentals under 30 days, which applies to the rental rate plus any cleaning fees or other charges. Virginia Beach, which encompasses much of the Long Island area, imposes an additional local transient occupancy tax of 8%, bringing the total tax rate to approximately 13.3%. These taxes are typically collected by Airbnb directly from guests at the time of booking and remitted to the Virginia Department of Taxation on behalf of hosts through their voluntary collection agreement established in 2019. Hosts must still register with the Virginia Department of Taxation to obtain a Certificate of Registration even when Airbnb collects taxes, and they remain ultimately responsible for ensuring proper tax compliance. Properties rented for 30 days or longer are generally exempt from transient occupancy taxes, and some localities may offer exemptions for rentals under certain dollar thresholds or for specific property types, though these vary by jurisdiction within the Virginia Beach metropolitan area.

Starting an Airbnb in Long Island, Virginia requires approximately $450,000-$550,000 in total initial investment. Property purchase costs average $380,000-$420,000 based on median home prices in the Long Island area of Virginia Beach. Furnishing costs typically range $15,000-$25,000 for a complete setup including furniture, appliances, linens, and décor to create an attractive rental space. Initial setup expenses including professional photography, listing creation, and marketing materials cost around $2,000-$3,000. Permits and fees vary by locality but generally include business license ($50-$200), short-term rental permit ($100-$500), and potential zoning compliance costs ($500-$1,500). Insurance for short-term rentals runs $2,000-$4,000 annually, with many requiring specialized STR coverage from companies like Proper Insurance or CBIZ. Utility setup and deposits for electricity, water, gas, internet, and cable total approximately $1,000-$2,000. First six months operating costs including utilities ($1,200-$1,800), cleaning services ($2,400-$3,600), maintenance reserves ($1,500-$2,500), platform fees to Airbnb and VRBO ($2,000-$4,000 assuming 60% occupancy), and miscellaneous supplies ($800-$1,200) add another $8,000-$13,000 to the startup investment.

Airbnb properties in Long Island, Virginia typically generate annual revenues between $25,000-$45,000 for well-positioned properties, with average daily rates ranging from $85-$150 depending on proximity to Virginia Beach and seasonal demand. Operating expenses generally consume 40-60% of gross revenue, including cleaning fees ($30-50 per turnover), property management (15-25% of revenue), utilities ($150-300 monthly), insurance ($1,200-2,000 annually), and maintenance costs averaging $2,000-4,000 yearly. Successful properties near the Chesapeake Bay or Virginia Beach oceanfront achieve profit margins of 25-35%, while inland properties typically see 15-25% margins. Key success factors include strategic location within 10 miles of major attractions, professional photography, dynamic pricing strategies, and maintaining 4.8+ star ratings. Properties with unique amenities like pools, hot tubs, or waterfront access command premium rates and achieve 70-80% occupancy rates during peak summer months (June-August), while off-season occupancy drops to 35-45%. The most profitable properties are typically 3-4 bedroom homes purchased for $300,000-500,000 that generate $30,000-40,000 annually after expenses, representing 8-12% returns on investment when factoring in property appreciation and tax benefits.

Airbnb investments in Long Island, Virginia typically generate annual ROI of 12-18% with cash-on-cash returns ranging from 8-14% depending on property location and seasonal demand. Properties in Virginia Beach and Norfolk areas show stronger performance with 15-20% annual returns due to consistent tourist traffic and military personnel housing needs. Initial profitability usually occurs within 8-14 months, with break-even on total investment typically achieved in 4-6 years. The Hampton Roads region demonstrates particularly strong metrics with average daily rates of $120-180 and occupancy rates of 65-75% annually, while properties near Virginia Beach oceanfront command premium rates of $200-350 per night during peak summer months, driving cash-on-cash returns up to 16-22% for well-positioned investments.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors, offering comprehensive market analysis and property recommendations for Long Island, Virginia markets. In the Long Island area, companies like Hamptons Real Estate Group and Douglas Elliman have specialized Airbnb investment divisions, while local services such as LI Vacation Rental Advisors and East End Property Solutions focus specifically on short-term rental acquisitions. National services including Awning, RedAwning, and AirDNA provide market analytics and property sourcing across Virginia markets, with AirDNA offering detailed revenue projections and occupancy data. Local Virginia specialists such as Richmond STR Properties, Virginia Beach Vacation Rental Experts, and Coastal Investment Realty have emerged since 2019 to serve the growing Airbnb investment market. Additional national platforms like Mashvisor, BiggerPockets, and Roofstock have expanded their services to include short-term rental property identification tools, while companies such as AvantStay and RedAwning offer end-to-end investment services including property acquisition, management, and optimization for both Long Island and Virginia markets.