Is Martha's Vineyard, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Martha's Vineyard, Massachusetts, begin by researching local zoning laws and regulations through the Martha's Vineyard Commission and individual town offices (Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark, or Aquinnah), as each town has specific short-term rental ordinances that typically require registration, annual permits costing $200-500, and compliance with occupancy limits and parking requirements. Obtain necessary permits including a business license, lodging tax registration with the Massachusetts Department of Revenue, and potentially a special permit for short-term rentals depending on your property's zoning district. Find a suitable property by working with local real estate agents familiar with rental regulations, focusing on areas zoned for tourist accommodations or mixed-use, with properties ranging from $800,000-$3,000,000 depending on location and size. Furnish the property with coastal-themed, durable furniture and amenities that appeal to summer visitors, including beach equipment, outdoor furniture, and high-quality linens, budgeting approximately $15,000-30,000 for a complete setup. List your property on Airbnb and VRBO with professional photography highlighting ocean views, proximity to beaches like South Beach or Menemsha, and island charm, setting competitive rates of $300-800 per night during peak summer season (June-September) and $150-400 during off-season. Manage the property by either hiring local property management companies like Martha's Vineyard Vacation Rentals or Island Rentals (charging 20-30% commission) or self-managing with reliable local cleaning services, maintenance contacts, and 24/7 guest communication, while ensuring compliance with the 9.7% Massachusetts short-term rental tax and local occupancy taxes.

To identify profitable short-term rental properties in Martha's Vineyard, Massachusetts, focus on locations within walking distance of popular beaches like South Beach in Edgartown or State Beach in Oak Bluffs, properties near downtown areas of Vineyard Haven, Edgartown, or Oak Bluffs for restaurant and shopping access, and homes offering water views or proximity to ferry terminals for guest convenience. Prioritize properties with 3-4 bedrooms, outdoor spaces like decks or patios, parking availability, and classic New England charm including features like widow's walks, shingle siding, or historic character that appeals to the island's affluent seasonal visitors. Conduct pricing analysis by researching comparable rentals on Airbnb and VRBO during peak summer months (June-September) when rates can reach $400-800+ per night, shoulder seasons (May, October) at $200-400 per night, and off-season rates, while factoring in Martha's Vineyard's premium market positioning compared to mainland Massachusetts properties. Research competition by analyzing occupancy rates, guest reviews, and pricing strategies of similar properties within your target neighborhoods, paying attention to unique selling points like beach access, historic significance, or luxury amenities. Utilize tools including AirDNA for market analytics specific to Martha's Vineyard, the Martha's Vineyard Commission for zoning and regulatory information, local real estate platforms like LandVest or Wallace & Co. Sotheby's International Realty for property searches, and connect with island-specific property management companies like Martha's Vineyard Vacation Rentals or Sandpiper Rentals for market insights and operational support.

To obtain an Airbnb/STR permit in Martha's Vineyard, Massachusetts, you must apply through the individual town where your property is located (Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark, or Aquinnah) as each town has its own regulations. Generally, you'll need to submit an application to the town's Building Department or Planning Board including a completed STR application form, proof of property ownership or lease agreement, floor plans showing maximum occupancy, parking plan demonstrating adequate off-street parking, septic system compliance certificate, fire safety inspection certificate, and liability insurance documentation of at least $1 million. Required documents typically include a site plan, abutters list, and sometimes a noise mitigation plan. Application fees range from $200-500 depending on the town, with annual renewal fees of $100-300. The approval timeline is generally 30-60 days but can extend to 90 days during peak season due to high application volumes. Specific Martha's Vineyard requirements include strict occupancy limits (often 2 people per bedroom plus 2 additional), mandatory 24/7 local contact person, quiet hours enforcement from 9 PM to 8 AM, and some towns require properties to be owner-occupied or have seasonal restrictions limiting rentals to certain months of the year.

Short-term rentals (STRs) are legal in Martha's Vineyard, Massachusetts, but operate under strict local regulations that vary by town across the island's six municipalities. As of 2023, towns like Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah each maintain their own STR ordinances with requirements typically including registration, licensing fees, occupancy limits, parking requirements, and noise restrictions. Many areas restrict STRs in certain residential zones or require special permits, with some towns limiting the total number of STR licenses available to preserve housing stock for year-round residents. Recent changes since 2020 have generally tightened regulations, with several towns implementing caps on new STR permits, increased enforcement measures, and higher fees in response to housing affordability concerns and community complaints about over-tourism. Property owners must comply with both state lodging regulations and local zoning laws, with violations potentially resulting in fines or permit revocation, making it essential to check specific requirements with each town's planning or licensing department before operating an STR.

The best Airbnb investment areas in Martha's Vineyard include Edgartown, which attracts premium tourists with its historic whaling captain homes, upscale shopping, and proximity to South Beach, commanding higher nightly rates year-round. Oak Bluffs offers strong rental potential due to its famous gingerbread cottages, vibrant nightlife scene, and the popular Flying Horses Carousel, drawing both families and younger visitors during peak summer months. Vineyard Haven (Tisbury) provides excellent investment opportunities as the main ferry terminal town, ensuring consistent guest traffic and serving business travelers and visitors seeking convenient access to the island's amenities. West Tisbury appeals to guests seeking rural charm and privacy, with properties near Menemsha fishing village and Lucy Vincent Beach commanding premium rates from affluent visitors. Chilmark and Aquinnah represent the highest-end investment opportunities, attracting wealthy vacationers willing to pay top dollar for secluded luxury accommodations near the famous Gay Head Cliffs and pristine beaches, though seasonal demand is more concentrated in summer months.

Airbnb properties in Martha's Vineyard, Massachusetts are subject to multiple lodging taxes including the Massachusetts state lodging excise tax of 5.7% on rentals under 90 days, plus local room occupancy taxes that vary by town - Edgartown charges 6%, Oak Bluffs 6%, Vineyard Haven 6%, West Tisbury 4%, Chilmark 6%, and Aquinnah 6% as of 2023. These taxes are typically collected automatically by Airbnb from guests at the time of booking for participating hosts, with Airbnb remitting payments directly to the Massachusetts Department of Revenue and local tax authorities on a monthly basis. Hosts who are not part of Airbnb's automatic collection program must register with the state and local tax authorities, collect taxes from guests, and remit payments quarterly along with required tax returns. The state tax applies to all short-term rentals under 90 consecutive days with no exemptions for small operators, while local taxes generally follow similar rules but may have minor variations in collection thresholds. Properties rented for 90 days or more to the same guest are typically exempt from these occupancy taxes, and some towns may offer exemptions for certain types of accommodations or during specific seasons, though these are rare and should be verified with local tax authorities.

The total cost to start an Airbnb in Martha's Vineyard, Massachusetts is approximately $1,850,000 to $2,100,000. Property purchase represents the largest expense at $1,600,000 to $1,800,000 for a median 3-bedroom home suitable for vacation rental. Furnishing costs range from $75,000 to $100,000 for high-quality furniture, appliances, linens, and décor that meets luxury vacation rental standards expected on the island. Initial setup costs including professional photography, listing creation, welcome materials, and technology setup total approximately $8,000 to $12,000. Permits and fees including short-term rental licenses, business registration, and local compliance requirements cost around $3,000 to $5,000 annually. Insurance for vacation rental properties on Martha's Vineyard runs $8,000 to $15,000 annually due to coastal location and higher property values. Utilities including electricity, water, internet, cable, and seasonal heating/cooling average $2,500 to $4,000 monthly. First six months operating costs encompassing utilities ($15,000 to $24,000), property management or cleaning services ($12,000 to $18,000), maintenance reserves ($5,000 to $8,000), marketing and platform fees ($3,000 to $5,000), and miscellaneous expenses ($5,000 to $7,000) total approximately $40,000 to $62,000.

Airbnb properties in Martha's Vineyard, Massachusetts demonstrate strong profitability potential with average nightly rates ranging from $300-800 during peak summer season (June-September) and $150-400 in shoulder seasons, generating annual revenues of $45,000-120,000 for well-positioned properties. Operating expenses typically include 25-30% for cleaning and maintenance, 3% Airbnb service fees, 8-12% property management if outsourced, utilities averaging $200-400 monthly, insurance premiums of $2,000-4,000 annually, and property taxes of $8,000-25,000 depending on assessed value. Net profit margins generally range from 35-55% for owner-operated properties, with waterfront and Oak Bluffs locations commanding premium rates. Success factors include proximity to beaches, ferry terminals, and downtown areas, with properties near South Beach, Edgartown Harbor, and Vineyard Haven performing exceptionally well. A typical 3-bedroom cottage near Katama Beach can generate $85,000 annually with $32,000 in expenses, yielding 62% profit margins, while properties managed by companies like RedAwning or Vacasa see margins drop to 25-35% due to higher management fees but benefit from professional marketing and operations.

Airbnb investments in Martha's Vineyard, Massachusetts typically generate annual ROI of 12-18% with cash-on-cash returns ranging from 8-15%, depending on property location and seasonal demand. Properties in prime locations like Edgartown or Oak Bluffs can achieve higher returns of 15-20% annually due to premium nightly rates of $400-800 during peak summer months (June-September), while off-season rates drop to $150-300. Initial profitability usually occurs within 18-24 months for well-positioned properties, with break-even points accelerated by the island's consistent demand from wealthy vacationers and limited inventory. Cash-on-cash returns are optimized when leveraging 70-80% financing on properties valued between $800K-2M, with gross rental yields of 6-10% before expenses, and net yields of 4-7% after accounting for property management, maintenance, and seasonal vacancy periods of 40-50% annually.

STRSearch is a national platform that specializes in identifying profitable short-term rental investment properties including those on Martha's Vineyard, Massachusetts. Local real estate agents who focus on Airbnb investments in Martha's Vineyard include Sandpiper Realty, Point B Realty, and Martha's Vineyard Real Estate which have agents experienced in vacation rental property analysis. National services that help investors find profitable Airbnb properties include Mashvisor, BiggerPockets, AirDNA, and Rabbu which provide market analytics and property identification tools for Martha's Vineyard. Local property management companies that also assist with investment property acquisition include Martha's Vineyard Vacation Rentals, Island Rentals Group, and Vineyard Square Properties. Additional national platforms serving the Martha's Vineyard market include RedAwning, AvantStay, and Vacasa which offer both property management and investment advisory services for short-term rental properties on the island.