Is Paia, Hawaii Good for Airbnb Investment?

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Paia, Hawaii Airbnb Investment Overview

Is Airbnb a Good Investment in Paia, Hawaii?

Investing in Airbnb properties in Paia, Hawaii, presents a unique and often challenging opportunity. While Maui's North Shore, including Paia, is a highly sought-after destination for its bohemian charm, surf culture, and natural beauty, the investment landscape is significantly shaped by stringent local regulations and exceptionally high property values. Current market conditions indicate a strong demand for short-term rentals, especially for unique or beachfront properties, driven by consistent tourism. However, the limited inventory of legal short-term rental units, coupled with a fiercely competitive real estate market, means that acquiring a profitable property requires substantial capital and careful navigation of the permitting process. Despite these hurdles, the consistent influx of tourists seeking authentic Hawaiian experiences ensures a strong potential for high occupancy rates and premium nightly rates for well-located and legally compliant Airbnb properties in Paia.

How Much Does an Average Airbnb Earn in Paia?

Based on available vacation rental data for Paia, Hawaii, Airbnb hosts typically earn between $3,500 to $8,000 per month, with oceanfront properties commanding the higher end of this range and inland accommodations averaging $3,500 to $5,500 monthly. Seasonal variations show peak earnings during winter months (December through March) when mainland visitors escape cold weather, with revenues increasing 40-60% above summer averages, while spring and fall represent shoulder seasons with moderate pricing. Summer months see strong demand from families but face increased competition from other vacation rentals. Key factors affecting earnings include proximity to beaches like Baldwin Beach Park and Ho'okipa, property amenities such as air conditioning and parking, accommodation size with 2-3 bedroom units performing best, and local events like surfing competitions that drive temporary demand spikes. Properties within walking distance of Paia town's restaurants and shops typically achieve 15-25% higher occupancy rates, while hosts offering additional services like beach equipment or local recommendations often see increased guest satisfaction and repeat bookings, though specific sourcing for this localized data remains limited due to the niche market size.

Airbnb Return on Investment in Paia

Airbnb investments in Paia, Hawaii typically generate ROI between 8-15% annually, with oceanfront and beachfront properties achieving the higher end of this range due to Paia's popularity as a surfing destination and gateway to the Road to Hana. The average daily rate for short-term rentals in Paia ranges from $200-400 depending on property size and proximity to Baldwin Beach Park, with occupancy rates averaging 65-75% throughout the year, peaking during winter surf season and summer vacation periods. Payback periods generally span 7-12 years for properties purchased at current market prices of $800,000-2,000,000, though this varies significantly based on initial investment and renovation costs. Compared to long-term rentals in Paia, which typically yield 4-6% annually due to limited rental inventory and high demand from locals and seasonal workers, Airbnb investments can generate 40-60% higher returns but require substantially more active management, higher operating expenses including cleaning fees and maintenance, and compliance with Maui County's short-term rental regulations. The premium returns reflect Paia's unique position as both a bohemian beach town and tourist hub, though investors must factor in Hawaii's high property taxes, insurance costs, and the seasonal nature of tourism revenue.

Average Airbnb Occupancy Rate in Paia

Airbnb occupancy rates in Paia, Hawaii typically average around 65-70% annually, with significant seasonal variation that peaks at 80-85% during winter months (December through March) when mainland visitors escape cold weather and surf conditions are optimal on Maui's North Shore. Summer months see moderate occupancy of 70-75%, while spring and fall experience the lowest rates at 55-65% due to less favorable weather and surf conditions. Paia's occupancy rates generally exceed Hawaii's statewide average of approximately 60-65% and significantly outperform the national Airbnb average of 48-52%, primarily due to its unique position as a gateway to the Road to Hana, proximity to world-class windsurfing and surfing beaches like Ho'okipa, and its bohemian charm that attracts both adventure seekers and cultural tourists. The town's limited hotel inventory and strong demand from international visitors, particularly during whale watching season and major surf competitions, help maintain these above-average occupancy levels throughout most of the year.

Best Neighborhoods for Airbnb in Paia

The most lucrative Airbnb neighborhoods in Paia center around the town's core near Baldwin Beach Park and the famous surf breaks, where properties command premium rates due to immediate beach access and proximity to Mama's Fish House, one of Maui's most renowned restaurants. The Kuau area offers exceptional investment potential with its direct oceanfront locations and access to world-class windsurfing at Hookipa Beach, attracting high-spending water sports enthusiasts year-round. Properties along Hana Highway near the Paia town center provide strong rental demand due to walkability to boutique shops, cafes, and the laid-back bohemian atmosphere that draws both surfers and tourists seeking authentic Hawaiian culture. The residential areas just mauka (inland) from the main strip offer better purchase prices while still maintaining short distances to beaches and town amenities, providing solid cash flow opportunities. Spreckelsville, technically adjacent to Paia, presents premium investment opportunities with luxury vacation rental potential due to its secluded beaches and upscale demographic of visitors willing to pay top dollar for privacy and exclusivity. The neighborhoods near the Paia Youth Center and community areas attract families and longer-term visitors, offering more stable occupancy rates though at moderate pricing. Properties positioned between Paia and the Road to Hana starting point capture both the town's amenities and serve as strategic bases for Hana adventure seekers, commanding strong seasonal rates during peak tourist months.

Short-term Rental Regulations in Paia

Short-term rental regulations in Paia, Hawaii are governed by Maui County ordinances that require all vacation rental operations to obtain a Short-Term Rental Home (STRH) permit or Bed & Breakfast Home (B&B) permit depending on the operation type. Properties must be located in areas zoned for such use, primarily in the Apartment, Hotel, or Business/Country Town districts, with most residential zones prohibiting short-term rentals entirely. Occupancy limits are typically restricted to two guests per bedroom plus two additional guests, with a maximum of 10 guests total for most properties. Owner-occupancy requirements vary by permit type, with B&B permits requiring the owner to live on-site while STRH permits do not have this requirement but are much more limited in availability. The registration process involves submitting detailed applications to Maui County including site plans, parking arrangements, and neighbor notification requirements, with fees ranging from $1,000 to $5,000 annually. Recent regulatory changes implemented around 2021-2022 have significantly tightened enforcement, increased penalties for unpermitted operations, and limited the number of new permits available, particularly in residential neighborhoods where community concerns about housing availability and neighborhood character have intensified.

Short-term Rental Fees and Taxes in Paia

Short-term rentals in Paia, Hawaii are subject to multiple fees and taxes including Hawaii's Transient Accommodations Tax (TAT) at 10.25% of gross rental receipts, Hawaii General Excise Tax (GET) at 4.712% on Maui, and Maui County's Real Property Tax which varies by property classification but typically ranges from $6.50 to $13.90 per $1,000 of assessed value annually for short-term rental properties. Operators must obtain a Conditional Permit from Maui County with application fees of approximately $5,000-$8,000 plus additional processing costs, and register for a TAT license with the Hawaii Department of Taxation for $20. Annual renewal fees for permits range from $500-$1,000 depending on the specific zoning and permit type. Additional costs may include business license fees of around $25-$50 annually, and potential homeowner association fees if applicable. Properties in certain areas may also be subject to special assessment districts with additional fees ranging from $100-$500 annually, and operators must maintain liability insurance which typically costs $800-$2,000 annually depending on coverage levels.

Is Airbnb a Good Investment in Paia, Hawaii?

Investing in Airbnb properties in Paia, Hawaii, presents a unique and often challenging opportunity. While Maui's North Shore, including Paia, is a highly sought-after destination for its bohemian charm, surf culture, and natural beauty, the investment landscape is significantly shaped by stringent local regulations and exceptionally high property values. Current market conditions indicate a strong demand for short-term rentals, especially for unique or beachfront properties, driven by consistent tourism. However, the limited inventory of legal short-term rental units, coupled with a fiercely competitive real estate market, means that acquiring a profitable property requires substantial capital and careful navigation of the permitting process. Despite these hurdles, the consistent influx of tourists seeking authentic Hawaiian experiences ensures a strong potential for high occupancy rates and premium nightly rates for well-located and legally compliant Airbnb properties in Paia.

How Much Does an Average Airbnb Earn in Paia?

Based on available vacation rental data for Paia, Hawaii, Airbnb hosts typically earn between $3,500 to $8,000 per month, with oceanfront properties commanding the higher end of this range and inland accommodations averaging $3,500 to $5,500 monthly. Seasonal variations show peak earnings during winter months (December through March) when mainland visitors escape cold weather, with revenues increasing 40-60% above summer averages, while spring and fall represent shoulder seasons with moderate pricing. Summer months see strong demand from families but face increased competition from other vacation rentals. Key factors affecting earnings include proximity to beaches like Baldwin Beach Park and Ho'okipa, property amenities such as air conditioning and parking, accommodation size with 2-3 bedroom units performing best, and local events like surfing competitions that drive temporary demand spikes. Properties within walking distance of Paia town's restaurants and shops typically achieve 15-25% higher occupancy rates, while hosts offering additional services like beach equipment or local recommendations often see increased guest satisfaction and repeat bookings, though specific sourcing for this localized data remains limited due to the niche market size.

Airbnb Return on Investment in Paia

Airbnb investments in Paia, Hawaii typically generate ROI between 8-15% annually, with oceanfront and beachfront properties achieving the higher end of this range due to Paia's popularity as a surfing destination and gateway to the Road to Hana. The average daily rate for short-term rentals in Paia ranges from $200-400 depending on property size and proximity to Baldwin Beach Park, with occupancy rates averaging 65-75% throughout the year, peaking during winter surf season and summer vacation periods. Payback periods generally span 7-12 years for properties purchased at current market prices of $800,000-2,000,000, though this varies significantly based on initial investment and renovation costs. Compared to long-term rentals in Paia, which typically yield 4-6% annually due to limited rental inventory and high demand from locals and seasonal workers, Airbnb investments can generate 40-60% higher returns but require substantially more active management, higher operating expenses including cleaning fees and maintenance, and compliance with Maui County's short-term rental regulations. The premium returns reflect Paia's unique position as both a bohemian beach town and tourist hub, though investors must factor in Hawaii's high property taxes, insurance costs, and the seasonal nature of tourism revenue.

Average Airbnb Occupancy Rate in Paia

Airbnb occupancy rates in Paia, Hawaii typically average around 65-70% annually, with significant seasonal variation that peaks at 80-85% during winter months (December through March) when mainland visitors escape cold weather and surf conditions are optimal on Maui's North Shore. Summer months see moderate occupancy of 70-75%, while spring and fall experience the lowest rates at 55-65% due to less favorable weather and surf conditions. Paia's occupancy rates generally exceed Hawaii's statewide average of approximately 60-65% and significantly outperform the national Airbnb average of 48-52%, primarily due to its unique position as a gateway to the Road to Hana, proximity to world-class windsurfing and surfing beaches like Ho'okipa, and its bohemian charm that attracts both adventure seekers and cultural tourists. The town's limited hotel inventory and strong demand from international visitors, particularly during whale watching season and major surf competitions, help maintain these above-average occupancy levels throughout most of the year.

Best Neighborhoods for Airbnb in Paia

The most lucrative Airbnb neighborhoods in Paia center around the town's core near Baldwin Beach Park and the famous surf breaks, where properties command premium rates due to immediate beach access and proximity to Mama's Fish House, one of Maui's most renowned restaurants. The Kuau area offers exceptional investment potential with its direct oceanfront locations and access to world-class windsurfing at Hookipa Beach, attracting high-spending water sports enthusiasts year-round. Properties along Hana Highway near the Paia town center provide strong rental demand due to walkability to boutique shops, cafes, and the laid-back bohemian atmosphere that draws both surfers and tourists seeking authentic Hawaiian culture. The residential areas just mauka (inland) from the main strip offer better purchase prices while still maintaining short distances to beaches and town amenities, providing solid cash flow opportunities. Spreckelsville, technically adjacent to Paia, presents premium investment opportunities with luxury vacation rental potential due to its secluded beaches and upscale demographic of visitors willing to pay top dollar for privacy and exclusivity. The neighborhoods near the Paia Youth Center and community areas attract families and longer-term visitors, offering more stable occupancy rates though at moderate pricing. Properties positioned between Paia and the Road to Hana starting point capture both the town's amenities and serve as strategic bases for Hana adventure seekers, commanding strong seasonal rates during peak tourist months.

Short-term Rental Regulations in Paia

Short-term rental regulations in Paia, Hawaii are governed by Maui County ordinances that require all vacation rental operations to obtain a Short-Term Rental Home (STRH) permit or Bed & Breakfast Home (B&B) permit depending on the operation type. Properties must be located in areas zoned for such use, primarily in the Apartment, Hotel, or Business/Country Town districts, with most residential zones prohibiting short-term rentals entirely. Occupancy limits are typically restricted to two guests per bedroom plus two additional guests, with a maximum of 10 guests total for most properties. Owner-occupancy requirements vary by permit type, with B&B permits requiring the owner to live on-site while STRH permits do not have this requirement but are much more limited in availability. The registration process involves submitting detailed applications to Maui County including site plans, parking arrangements, and neighbor notification requirements, with fees ranging from $1,000 to $5,000 annually. Recent regulatory changes implemented around 2021-2022 have significantly tightened enforcement, increased penalties for unpermitted operations, and limited the number of new permits available, particularly in residential neighborhoods where community concerns about housing availability and neighborhood character have intensified.

Short-term Rental Fees and Taxes in Paia

Short-term rentals in Paia, Hawaii are subject to multiple fees and taxes including Hawaii's Transient Accommodations Tax (TAT) at 10.25% of gross rental receipts, Hawaii General Excise Tax (GET) at 4.712% on Maui, and Maui County's Real Property Tax which varies by property classification but typically ranges from $6.50 to $13.90 per $1,000 of assessed value annually for short-term rental properties. Operators must obtain a Conditional Permit from Maui County with application fees of approximately $5,000-$8,000 plus additional processing costs, and register for a TAT license with the Hawaii Department of Taxation for $20. Annual renewal fees for permits range from $500-$1,000 depending on the specific zoning and permit type. Additional costs may include business license fees of around $25-$50 annually, and potential homeowner association fees if applicable. Properties in certain areas may also be subject to special assessment districts with additional fees ranging from $100-$500 annually, and operators must maintain liability insurance which typically costs $800-$2,000 annually depending on coverage levels.

* 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.

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Everything Smart Investors Ask About STR Wealth Building

How to start an Airbnb in Paia, Hawaii?

To start an Airbnb in Paia, Hawaii, begin by researching Maui County's strict short-term rental regulations, as Paia falls under County of Maui jurisdiction which requires a Conditional Permit for short-term rentals under 180 days, with applications typically costing $5,000-$10,000 and taking 6-12 months for approval through the Planning Department. Obtain necessary permits including a General Excise Tax License from Hawaii Department of Taxation, Transient Accommodations Tax permit, and ensure compliance with fire safety codes and building permits if renovating. Find a suitable property in Paia's residential or hotel-zoned areas, noting that many residential zones prohibit short-term rentals entirely, so focus on properties already zoned appropriately or grandfathered in before the 2021 moratorium. Furnish the space with tropical, durable furniture suitable for Hawaii's humid climate, including quality linens, kitchen essentials, beach equipment, and safety items like smoke detectors and first aid kits. List your property on Airbnb and other platforms with professional photography highlighting Paia's proximity to Ho'okipa Beach, Mama's Fish House, and the Road to Hana, setting competitive rates typically ranging $150-$400 per night depending on size and amenities. Manage the property by establishing relationships with local cleaning services, maintenance contractors, and consider hiring a property management company familiar with Maui County regulations, while maintaining detailed records for tax purposes and ensuring 24/7 guest communication, as Maui County requires hosts to be available or have local representation at all times.

What's the best way to identify good STR properties in Paia, Hawaii?

To identify profitable short-term rental properties in Paia, Hawaii, focus on locations within walking distance of Baldwin Beach Park and Ho'okipa Beach, as these areas command premium rates due to their proximity to world-renowned windsurfing spots and pristine beaches. Target properties with 2-3 bedrooms, outdoor spaces like lanais or gardens, parking availability, and authentic Hawaiian architectural features, as these consistently outperform generic condos in occupancy rates. Conduct pricing analysis by monitoring comparable properties on Airbnb and VRBO during peak seasons (December-April and June-August), aiming for properties that can achieve $200-400 per night depending on size and amenities. Research competition by analyzing the saturation of STRs in specific neighborhoods, with lower density areas near Paia Bay or along Hana Highway offering better profit potential than oversaturated beachfront strips. Utilize tools like AirDNA for market analytics, STR Helper for revenue projections, and local resources such as Maui County's STR permit database to verify legal compliance, while connecting with Maui-based property management companies like RedAwning or Vacasa to understand operational costs and market dynamics specific to Paia's unique tourism patterns driven by windsurfing, surfing, and the Road to Hana starting point.

How to get an Airbnb permit in Paia, Hawaii?

To obtain an Airbnb/STR permit in Paia, Hawaii, you must apply through Maui County's Department of Planning since Paia is located in Maui County. Begin by submitting a Short-Term Rental Home (STRH) permit application to the Maui County Planning Department, which requires a completed application form, property tax records, floor plans drawn to scale, site plan showing the property layout, proof of ownership or authorization from owner, general excise tax license, transient accommodations tax license from the State of Hawaii, and a $5,000 application fee. The process typically takes 6-12 months due to extensive review requirements and community input periods. Paia-specific requirements include compliance with the West Maui Community Plan, adherence to agricultural zoning restrictions if applicable, parking requirements of at least two off-street spaces, maximum occupancy limits based on bedroom count, noise ordinance compliance, and demonstration that the property meets all building and safety codes. You must also attend a public hearing if required and obtain approval from the Maui Planning Commission. Additional fees may include inspection costs ($200-500) and annual renewal fees ($1,000-2,000). The permit, if approved, is valid for one year and must be renewed annually with updated documentation and fees.

Is it legal to operate a short-term rental in Paia, Hawaii?

Short-term rentals (STRs) in Paia, Hawaii are heavily restricted under Maui County's current regulations. As of 2021-2022, Maui County implemented strict ordinances that effectively prohibit new STR permits in most residential areas, including Paia, which is located in an area zoned primarily for residential use. Existing legal STRs with proper permits can continue operating, but new permits are generally not being issued for residential zones. The county has been cracking down on illegal vacation rentals through increased enforcement and substantial fines, with violations potentially reaching $20,000 per day. Paia, being a popular tourist destination on Maui's North Shore, has been particularly affected by these restrictions as the county aims to preserve housing for local residents. Property owners in Paia can only legally operate STRs if they obtained permits before the moratorium or if their property is in a zone that still allows such use, which is extremely limited. The legal changes were driven by the housing crisis affecting local residents who were being priced out by vacation rental conversions.

What are the best places to invest in Airbnb in Paia, Hawaii?

The best areas for Airbnb investment in Paia, Hawaii include the beachfront properties along Paia Bay and Baldwin Beach Park area, which attract surfers and beach enthusiasts year-round due to the world-class windsurfing and kitesurfing conditions at nearby Hookipa Beach. The historic Paia Town center offers excellent walkability to restaurants, shops, and cafes, making it highly desirable for tourists seeking an authentic Hawaiian experience without needing rental cars. Properties near the Hana Highway entrance are particularly valuable as Paia serves as the last major stop before the famous Road to Hana, creating consistent demand from travelers starting early morning drives or returning late from day trips. The residential areas between Paia and Haiku offer more affordable investment opportunities while still providing easy access to beaches and town amenities, attracting longer-stay visitors and digital nomads. The proximity to Mama's Fish House, one of Maui's most renowned restaurants, adds significant appeal to nearby properties, while the area's reputation as a bohemian surf town continues to draw international visitors seeking the laid-back North Shore lifestyle that has been popular since the 1970s.

Airbnb and lodging taxes in Paia, Hawaii

Airbnb properties in Paia, Hawaii are subject to multiple lodging and occupancy taxes including Hawaii's General Excise Tax (GET) of 4.712% on gross rental income, the Transient Accommodations Tax (TAT) of 10.25% on gross rental receipts, and Maui County's additional TAT surcharge of 3% as of 2021, bringing the total tax burden to approximately 17.962%. These taxes are typically collected from guests at the time of booking through Airbnb's automatic tax collection system for properties rented less than 180 days, with Airbnb remitting GET and TAT directly to the Hawaii Department of Taxation monthly. Property owners must register for a GET license and TAT certificate, file returns even when Airbnb collects taxes, and are responsible for collecting and remitting taxes directly if they use other platforms or rent for 180+ days. Exemptions are limited and generally apply only to rentals exceeding 180 consecutive days to the same guest, which are considered long-term leases rather than transient accommodations, though owners must still verify exemption eligibility and maintain proper documentation.

Total cost to purchase, furnish and operate an Airbnb in Paia, Hawaii

Starting an Airbnb in Paia, Hawaii requires significant upfront investment with property purchase being the largest expense at approximately $1,200,000 for a median-priced home suitable for vacation rental. Furnishing costs typically range $25,000-$40,000 for a complete tropical-themed setup including furniture, appliances, linens, and decor. Initial setup expenses including professional photography, listing creation, and marketing materials cost around $3,000-$5,000. Permits and fees in Maui County include transient vacation rental permits ($5,000-$10,000), business licenses ($500), and tax registrations totaling approximately $6,000-$11,000. Insurance premiums for short-term rental coverage average $4,000-$6,000 annually. Utility deposits and connections for electricity, water, internet, and cable typically cost $2,000-$3,000. First six months operating costs including utilities ($1,200/month), cleaning services ($150 per turnover), property management fees (20-30% of revenue), maintenance reserves, and supplies total approximately $15,000-$20,000. The total estimated startup cost ranges from $1,255,000 to $1,285,000, making Paia one of the more expensive markets for Airbnb investment due to its prime beachfront location and limited housing inventory.

Are Airbnb properties in Paia, Hawaii profitable?

Airbnb properties in Paia, Hawaii demonstrate strong profitability potential with average daily rates ranging from $180-350 for beachfront properties and $120-220 for inland locations, generating annual revenues of $45,000-85,000 for well-managed properties with 65-75% occupancy rates. Operating expenses typically consume 35-45% of gross revenue, including cleaning fees ($75-125 per turnover), property management (15-25%), utilities ($200-400 monthly), insurance ($2,000-4,000 annually), and maintenance costs averaging $3,000-6,000 yearly due to salt air corrosion and high usage. Net profit margins generally range from 25-40% for owner-operated properties, with successful hosts like those managing converted plantation-style homes near Baldwin Beach Park achieving $35,000-50,000 annual profits on properties valued at $800,000-1.2 million. Key success factors include proximity to Paia Bay and Ho'okipa Beach, unique architectural features like traditional Hawaiian design elements, premium amenities such as outdoor showers and lanais, professional photography showcasing ocean views, and responsive guest communication, with top-performing properties maintaining 4.8+ star ratings and commanding 20-30% premium pricing over comparable mainland vacation rentals.

What is the expected return on investment for an Airbnb in Paia, Hawaii?

Airbnb investments in Paia, Hawaii typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% due to the area's strong tourist demand driven by its proximity to Hana Highway, Hookipa Beach surfing, and North Shore attractions. Properties in Paia command average daily rates of $200-350 depending on size and oceanfront proximity, with occupancy rates averaging 70-80% annually, though seasonal fluctuations occur with peak winter months (December-March) and summer periods (June-August) performing strongest. Initial profitability typically occurs within 18-24 months for well-positioned properties, with investors like RedAwning and Vacasa reporting consistent performance in the market, though higher property acquisition costs ($800K-1.5M average) and Hawaii's strict short-term rental regulations including county permits and tax obligations (13.25% combined state and county transient accommodation tax) impact overall returns. The market has shown resilience post-2020 with companies like Airbnb reporting Maui bookings recovering to pre-pandemic levels by 2022, making Paia a viable but capital-intensive investment requiring thorough due diligence on zoning compliance and property management logistics.

What company can help me find and buy a profitable Airbnb in Paia, Hawaii?

STRSearch is a national platform that specializes in identifying profitable short-term rental properties for investors looking in Paia, Hawaii. Local real estate agents like Compass Maui, Coldwell Banker Island Properties, and Hawaii Life Real Estate Brokers have extensive experience with vacation rental properties in the Paia area and understand the local zoning laws and permit requirements. National services include Mashvisor, which provides Airbnb analytics and investment property data, AirDNA for market analysis and revenue projections, and BiggerPockets for connecting with other investors and finding deals. Local property management companies such as RedAwning, Vacasa, and Elite Pacific Properties can help investors identify properties with strong rental potential while also offering management services. Maui-specific real estate firms like Maui Real Estate Team and Berkshire Hathaway HomeServices Island Properties have agents who specialize in investment properties in beach communities like Paia. Additional national platforms include Roofstock, which focuses on investment properties, and local vacation rental consultants who understand Maui County's short-term rental regulations and can guide investors through the complex permitting process required for legal Airbnb operations in Paia.

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