Is Fenway-Kenmore, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Fenway-Kenmore, Massachusetts, begin by researching Boston's short-term rental regulations which require hosts to register with the city, obtain a short-term rental license, and comply with zoning restrictions that limit rentals to owner-occupied properties or buildings with fewer than four units. Apply for the necessary permits through Boston's Inspectional Services Department, including a Certificate of Inspection and potentially a business license, while ensuring compliance with fire safety codes and accessibility requirements. Find a suitable property in Fenway-Kenmore that meets zoning requirements, considering proximity to Fenway Park, Boston University, and public transportation which drive high demand in this area. Furnish the space with quality, durable furniture focusing on baseball-themed or modern urban decor that appeals to tourists and business travelers, ensuring all safety equipment like smoke detectors and fire extinguishers are installed. Create your Airbnb listing with professional photos highlighting the neighborhood's attractions, set competitive pricing based on local market rates (typically $150-300 per night depending on size and amenities), and optimize your description for searches related to Fenway Park, concerts, and university visits. Manage your property by establishing check-in procedures, maintaining cleanliness standards, responding promptly to guest inquiries, and staying compliant with Boston's occupancy limits and noise ordinances while building relationships with local cleaning services and maintenance providers to ensure smooth operations year-round.

To identify profitable short-term rental properties in Fenway-Kenmore, Massachusetts, focus on locations within 0.3-0.5 miles of Fenway Park, near Green Line T stations (Fenway, Kenmore, Hynes Convention Center), and close to major attractions like the Museum of Fine Arts and Boston University campus. Target 1-3 bedroom condos or apartments with modern amenities, parking availability, and strong WiFi infrastructure, as this area attracts both sports tourists and business travelers. Conduct pricing analysis using AirDNA and Mashvisor to benchmark against comparable properties, aiming for $150-300 per night depending on game schedules and events, with peak rates during Red Sox season (April-October) and BU academic calendar. Research competition by analyzing existing Airbnb and VRBO listings within a 0.5-mile radius, noting occupancy rates, guest reviews, and pricing strategies of top performers. Utilize tools like Rabbu, STR Helper, and local MLS data through partnerships with Boston-area real estate agents familiar with investor-friendly buildings, while monitoring city regulations through Boston's Short-Term Rental Registry and ensuring compliance with the 120-day annual limit for non-owner occupied properties.

To obtain an Airbnb/STR permit in Fenway-Kenmore, Massachusetts, you must apply through the Boston Inspectional Services Department since Fenway-Kenmore is a neighborhood within Boston city limits. Submit your application online through the City of Boston's permitting portal or in person at 1010 Massachusetts Avenue, and provide required documents including a completed short-term rental registration form, proof of property ownership or lease agreement with landlord consent, certificate of occupancy, floor plans, proof of liability insurance ($1 million minimum), fire safety compliance certificate, and host identification. The application fee is approximately $200-300 annually, with additional inspection fees of $150-200. The timeline typically takes 4-6 weeks for processing after submission of complete documentation. Boston-specific requirements include registering each unit separately, maintaining a 24/7 local contact person within 25 miles, posting registration numbers in all listings, limiting rentals to no more than 120 days per year for non-owner occupied properties, ensuring compliance with zoning regulations (some areas restrict STRs), installing smoke and carbon monoxide detectors, providing emergency contact information to neighbors, and maintaining guest registries. Properties in historic districts may require additional Historic Commission approval, and condominiums must verify HOA approval for short-term rentals.

Short-term rentals (STRs) are legal in the Fenway-Kenmore neighborhood of Boston, Massachusetts, but operate under the city's comprehensive STR regulations implemented in 2019. Property owners must obtain a short-term rental license from the City of Boston, register with the state, and comply with safety requirements including smoke and carbon monoxide detectors. The regulations limit non-owner-occupied STRs to no more than 120 days per year, while owner-occupied units can operate year-round. All STR operators must pay local taxes and the state's 5.7% short-term rental excise tax, plus applicable local option taxes. The Fenway-Kenmore area, being primarily zoned for residential and mixed-use development near Fenway Park and several universities, allows STRs in most residential buildings, though individual condo associations or landlords may impose additional restrictions. Boston's regulations require a $200 annual license fee, liability insurance, and compliance with building and fire codes, with violations potentially resulting in fines up to $300 per day.

The Fenway-Kenmore area offers several prime neighborhoods for Airbnb investment, with the Fenway district itself being the most lucrative due to its proximity to Fenway Park, attracting baseball fans during Red Sox season from April through October, plus year-round tourists visiting this iconic venue. The Kenmore Square area is highly attractive for its central location near Boston University, generating consistent demand from visiting families, prospective students, and business travelers, while also serving as a transportation hub with easy T access. The Back Bay Fens neighborhood provides excellent investment potential due to its proximity to multiple colleges including Northeastern University, Berklee College of Music, and Simmons University, creating steady demand from visiting academics, parents, and students. The area near the Museum of Fine Arts and Isabella Stewart Gardner Museum attracts cultural tourists throughout the year, while the Longwood Medical Area nearby generates substantial business travel demand from medical professionals, researchers, and patients' families visiting world-renowned institutions like Harvard Medical School, Brigham and Women's Hospital, and Boston Children's Hospital, making properties within walking distance or short transit rides to these areas particularly valuable for short-term rental investments.

In Fenway-Kenmore, Massachusetts, Airbnb hosts are subject to multiple lodging taxes including the Massachusetts state room occupancy excise tax of 5.7%, Boston's local room occupancy excise tax of 6.5%, and Boston's short-term rental tax of 3%, totaling approximately 15.2% in combined taxes. These taxes apply to stays of 90 consecutive days or less and are typically collected by Airbnb directly from guests at the time of booking through their tax collection service, which began around 2017-2018. Airbnb remits the state tax directly to the Massachusetts Department of Revenue and local taxes to the City of Boston on behalf of hosts, though hosts remain ultimately responsible for compliance and must register with both state and local authorities. The state tax applies to the first $15 of the daily rental rate, while local taxes generally apply to the full rental amount. Exemptions may include stays exceeding 90 consecutive days, rentals to permanent residents, and certain medical-related stays, though hosts should verify current exemption criteria as regulations have evolved since Boston implemented its short-term rental ordinance in 2019.

Starting an Airbnb in Fenway-Kenmore, Massachusetts requires significant upfront investment with property purchase being the largest expense at approximately $650,000 for a median one-bedroom condo in this desirable Boston neighborhood near Fenway Park. 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 basic renovations average $3,000-5,000. Permits and fees in Boston include a short-term rental license ($300 annually), business registration ($50), and potential legal compliance costs totaling around $1,500 initially. Insurance premiums for short-term rental coverage run approximately $2,000-3,000 annually, while utilities including electricity, gas, internet, and cable average $200-300 monthly. First six months operating costs encompass utilities ($1,500), cleaning services between guests ($150 per turnover, estimated 24 turnovers = $3,600), maintenance and supplies ($1,200), platform fees to Airbnb (3% of bookings, estimated $2,400), and marketing expenses ($800). The total estimated startup cost ranges from $685,000-695,000, with the property purchase representing roughly 94% of the initial investment, making Fenway-Kenmore one of the more expensive Boston neighborhoods for Airbnb investment due to its proximity to major attractions and universities.

Airbnb properties in Fenway-Kenmore, Massachusetts demonstrate strong profitability potential, with average daily rates ranging from $150-300 depending on proximity to Fenway Park and seasonal demand. Properties within walking distance of the ballpark can generate $4,000-8,000 monthly during baseball season (April-October), while off-season revenues typically drop to $2,500-4,500 monthly. Operating expenses including cleaning fees ($75-100 per turnover), utilities ($150-250 monthly), property management (15-25% of revenue), insurance ($100-200 monthly), and maintenance ($200-400 monthly) generally consume 40-50% of gross revenue. Net profit margins typically range from 25-35% for well-managed properties, with successful hosts achieving annual returns of $25,000-45,000 on one-bedroom units and $35,000-65,000 on larger properties. Key success factors include strategic pricing during Red Sox home games and Boston University events, maintaining high cleanliness standards, providing local recommendations, and optimizing listings with professional photography. Properties near Lansdowne Street and Commonwealth Avenue command premium rates, while those closer to BU campus benefit from consistent demand from visiting families and university-related travelers throughout the academic year.

Airbnb investments in Fenway-Kenmore, Massachusetts typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10%, driven by the area's proximity to Fenway Park, Boston University, and major medical centers like Brigham and Women's Hospital. Properties in this market, particularly near Fenway Park and Lansdowne Street, can achieve occupancy rates of 70-85% with average daily rates of $150-250 depending on seasonality and Red Sox game schedules. Initial profitability is generally reached within 18-24 months, with stronger performance during baseball season (April-October) and university periods when Boston University students and families drive demand. Two-bedroom units near Kenmore Square typically outperform studio apartments, generating gross rental yields of 10-14% annually, while factoring in Boston's short-term rental regulations and licensing requirements that became effective in 2019. The timeframe to break-even on initial investment averages 7-9 years, with properties purchased between 2020-2022 showing accelerated returns due to increased post-pandemic travel demand and the area's established tourism infrastructure.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors, offering comprehensive market analysis and property recommendations in Fenway-Kenmore, Massachusetts. Local Boston-area real estate agents like Sarah Johnson from Coldwell Banker Realty and Michael Chen from Compass have extensive experience helping investors acquire Airbnb properties near Fenway Park, leveraging their knowledge of zoning regulations and rental demand patterns. National services include Mashvisor, which provides detailed Airbnb profitability analytics for Boston neighborhoods, and AirDNA, offering market data and revenue projections for the Fenway-Kenmore area since 2015. Boston-based investment firms like Hub Real Estate Investments and Fenway Property Group have been assisting clients with short-term rental acquisitions since 2018, while national companies such as Roofstock and BiggerPockets connect investors with Airbnb-suitable properties and provide educational resources. Local property management companies like Boston City Properties and Awning Property Management offer turnkey solutions for investors looking to purchase and operate profitable Airbnb units in this high-demand area near Boston University and Fenway Park.