Is Wailea, Hawaii Good for Airbnb Investment?

To start an Airbnb in Wailea, Hawaii, begin by researching Maui County's strict short-term rental regulations, which require properties to be in designated zones and comply with the Conditional Permit system established around 2021. Obtain necessary permits including a Conditional Use Permit from Maui County Planning Department, General Excise Tax License from Hawaii Department of Taxation, and Transient Accommodations Tax registration, with application fees ranging from $500-2,000 and processing times of 6-12 months. Find a suitable property in approved resort or hotel-zoned areas like Grand Wailea Resort vicinity or designated vacation rental districts, with purchase prices typically ranging $800,000-3,000,000 for condos and $2-10 million for homes. Furnish the property with high-end, tropical-themed furniture, quality linens, full kitchen amenities, beach equipment, and safety features like smoke detectors and first aid kits, budgeting $15,000-50,000 depending on property size. List your property on Airbnb, VRBO, and local platforms with professional photography highlighting ocean views and resort amenities, setting competitive rates of $200-800 per night based on property type and season. Manage the property by hiring local cleaning services ($75-150 per turnover), maintenance contractors, and consider property management companies charging 15-25% of revenue, while maintaining 24/7 guest communication and ensuring compliance with occupancy limits and noise ordinances specific to Wailea's resort community standards.

To identify profitable short-term rental properties in Wailea, Hawaii, focus on oceanfront or ocean-view locations within walking distance to luxury resorts like Grand Wailea and Fairmont Kea Lani, as proximity to beaches like Wailea Beach and Polo Beach commands premium rates of $400-800+ per night. Target properties with 2-4 bedrooms, modern Hawaiian-style architecture, private pools or hot tubs, high-end finishes, and outdoor living spaces that can accommodate 4-8 guests, as these features justify rates 30-50% above standard condos. Analyze comparable properties using AirDNA and Mashvisor to identify average daily rates ($300-600 for condos, $500-1200 for homes), occupancy rates (typically 65-75% annually), and seasonal demand patterns with peak rates during winter months (December-April) and summer holidays. Research competition by examining listings in Wailea resort complexes like Wailea Beach Villas, Palms at Wailea, and Ho'olei, noting their amenities, pricing strategies, and guest reviews to identify market gaps. Utilize tools like Rabbu, AllTheRooms, and local MLS data through Coldwell Banker or Compass Maui agents, while consulting Hawaii's county regulations for short-term rental permits and HOA restrictions, as many Wailea properties have specific rental policies that can impact profitability and legal operation.

To obtain an Airbnb/STR permit in Wailea, Hawaii, you must apply through Maui County's Department of Planning since Wailea is located in Maui County. Begin by submitting a Short-Term Rental Home (STRH) application to the Maui County Planning Department, which can be done online through their permitting portal or in person at 2200 Main Street, Suite 315, Wailuku, HI 96793. Required documents include a completed application form, property deed or lease agreement, tax map key information, floor plans, site plan, proof of general excise tax license, transient accommodations tax registration, liability insurance certificate ($1 million minimum), and neighbor notification affidavits. The application fee is approximately $5,000 with additional fees for inspections and processing totaling around $6,500-$7,000. Wailea-specific requirements include compliance with South Maui Community Plan guidelines, adherence to resort zoning regulations, maximum occupancy limits based on bedrooms (typically 2 guests per bedroom plus 2 additional), parking requirements (one space per bedroom), and maintaining the property's residential character. The timeline typically ranges from 6-12 months due to required public hearings, neighbor notification periods (45 days), planning commission review, and final approval processes. Properties in Wailea must also comply with homeowners association rules and may face additional restrictions due to the area's resort designation and luxury residential zoning requirements.

Short-term rentals (STRs) in Wailea, Hawaii are legal but heavily regulated under Maui County's strict ordinances implemented in recent years. As of 2021-2022, Maui County significantly tightened STR regulations, requiring all operators to obtain proper permits and comply with zoning restrictions, with many areas in resort-zoned districts like Wailea being more permissive than residential neighborhoods. Wailea, being primarily a resort destination area, generally allows STRs in appropriately zoned properties, particularly in resort and hotel districts, but operators must secure transient vacation rental (TVR) permits or conditional permits, maintain proper insurance, pay transient accommodation taxes, and adhere to occupancy limits and noise restrictions. The county has been actively enforcing these regulations since 2022, with unpermitted operations facing significant fines, and there's been ongoing discussion about further restrictions to address housing shortages and community concerns. Properties in Wailea's resort areas typically have more flexibility for STR operations compared to residential zones elsewhere on Maui, but all operators must comply with county registration requirements, safety standards, and tax obligations.

The best areas for Airbnb investment in Wailea, Hawaii include the Wailea Resort area along Wailea Alanui Drive, which offers proximity to luxury resorts like Grand Wailea and Fairmont Kea Lani, attracting high-end tourists year-round who seek upscale accommodations near world-class beaches and golf courses. The Wailea Beach Walk district is particularly attractive due to its direct beach access, luxury shopping at The Shops at Wailea, and fine dining options, drawing affluent travelers willing to pay premium rates for convenience and luxury. The Makena area, just south of Wailea proper, offers excellent investment potential with its secluded beaches like Makena Beach and Big Beach, appealing to tourists seeking privacy and natural beauty while remaining close to Wailea's amenities. The Wailea Golf Course neighborhoods, including areas near the Gold, Emerald, and Blue courses, attract golf enthusiasts and luxury travelers, particularly during peak seasons from December through April when mainland visitors escape winter weather. The Polo Beach and Wailea Beach vicinity commands high nightly rates due to direct beach access and proximity to snorkeling spots, while the upper Wailea residential areas offer stunning ocean views and privacy that justify premium pricing for discerning guests seeking exclusive Hawaiian experiences.

Airbnb properties in Wailea, Hawaii are subject to multiple lodging taxes including Hawaii's Transient Accommodations Tax (TAT) of 10.25% and Maui County's Real Property Tax on short-term rentals. The TAT applies to all stays under 180 days and is collected by the state, with hosts required to register for a TAT license and file monthly returns by the 20th of the following month, remitting taxes even if no bookings occurred. Maui County imposes additional requirements including a 3% county surcharge on transient accommodations and higher property tax rates for short-term rental properties, typically ranging from $10-15 per $1,000 of assessed value compared to $2-6 for residential properties. Hosts must also obtain a Maui County Tax Map Key number and may need conditional permits or non-conforming use certificates depending on zoning. The General Excise Tax (GET) of 4.712% also applies to rental income. Airbnb may collect and remit TAT on behalf of hosts in Hawaii, but hosts remain responsible for ensuring compliance and may need to register separately for county taxes and permits. There are limited exemptions for properties rented for 180+ consecutive days to the same tenant, which would be classified as long-term rentals rather than transient accommodations.

Starting an Airbnb in Wailea, Hawaii requires significant upfront investment due to the area's luxury market positioning. Property purchase costs average $2.8-4.2 million for a median 2-3 bedroom condo suitable for vacation rentals, with oceanfront properties commanding premium prices. Furnishing costs range $75,000-125,000 to meet luxury guest expectations with high-end furniture, appliances, linens, and Hawaiian-themed decor. Initial setup expenses include $15,000-25,000 for professional photography, listing optimization, welcome amenities, and technology installations. Permits and fees total approximately $8,000-12,000 including Maui County short-term rental permits ($1,000 annually), business licenses, tax registrations, and legal compliance costs. Insurance premiums run $8,000-15,000 annually for comprehensive coverage including liability, property damage, and vacation rental specific policies. Utility setup and deposits cost $2,000-3,500 covering electricity, water, internet, cable, and trash services. First six months operating costs average $35,000-50,000 including property management fees (20-30% of revenue), cleaning services ($150-250 per turnover), maintenance, supplies, marketing, and platform commissions to Airbnb and VRBO. Total startup investment ranges $3.0-4.5 million, with ongoing monthly expenses of $6,000-8,500 before mortgage payments, making Wailea one of the most expensive Airbnb markets globally.

Airbnb properties in Wailea, Hawaii demonstrate strong profitability potential with average daily rates ranging from $400-800 for luxury condos and $800-2,000 for premium vacation homes, generating annual revenues of $80,000-400,000 depending on property type and occupancy rates of 65-75%. Operating expenses typically include property management fees (20-30%), cleaning costs ($150-300 per turnover), utilities ($200-500 monthly), insurance ($3,000-8,000 annually), and maintenance reserves (5-10% of revenue), resulting in net profit margins of 25-45% for well-managed properties. Success factors include proximity to Wailea Beach Resort, Grand Wailea, and championship golf courses, with properties within walking distance to beaches commanding premium rates. A typical 2-bedroom oceanview condo purchased for $1.2 million in 2019 generates approximately $120,000 annual revenue with $75,000 in expenses, yielding $45,000 net profit and 3.75% cash-on-cash return, while luxury 4-bedroom homes near the Fairmont Kea Lani can achieve 6-8% returns. Peak performance occurs during winter months (December-April) when mainland visitors escape cold weather, and properties featuring amenities like pools, ocean views, and concierge services consistently outperform basic accommodations by 30-50% in both occupancy and nightly rates.

Airbnb investments in Wailea, Hawaii typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% based on current market conditions. Properties in luxury resort areas like the Grand Wailea and Fairmont Kea Lani vicinity command nightly rates of $400-800, with occupancy rates averaging 70-75% annually due to consistent tourist demand. Initial investment costs range from $1.2-3.5 million for condos and vacation rentals, with investors typically reaching profitability within 18-24 months after accounting for property management fees (25-30%), maintenance, insurance, and Hawaii's transient accommodation tax of 10.25%. The premium Wailea market benefits from year-round demand driven by luxury travelers, with peak seasons (December-April and June-August) generating 40% higher rates, though investors should factor in potential regulatory changes as Maui County continues evaluating short-term rental policies that could impact future returns.

STRSearch leads the market in Airbnb investment property analysis for Wailea, Hawaii, providing comprehensive data on rental performance and market trends. Local specialists include Maui Real Estate Advisors, Pacific Rim Properties, and Wailea Realty Group, who have deep knowledge of the luxury vacation rental market in this premium resort area. National services like Awning, Mashvisor, and RedAwning offer property search tools and investment analysis specifically for short-term rental properties. Compass Real Estate and Coldwell Banker Island Properties maintain strong presences in Wailea with agents experienced in vacation rental investments. AirDNA provides market data and revenue projections, while companies like Vacasa and RedAwning offer full-service property management for investors. Local property management firms such as Maui Vacation Advisors and Elite Pacific Properties specialize in luxury Airbnb operations in the Wailea area. Investment-focused platforms like Roofstock and BiggerPockets connect investors with Wailea properties, though inventory in this high-end market launched around 2015-2018 for most digital platforms, with traditional luxury real estate firms like Sotheby's International Realty and Hawaii Life Real Estate Brokers maintaining the longest track records serving high-net-worth Airbnb investors in this exclusive South Maui destination.