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The federal government has finalized a significant new reporting rule that will impact certain residential real estate transactions beginning in 2026. For short, we are going to refer to this as the FinCEN Real Estate Reporting Rule 2026. As a Maui-born real estate advisor licensed since 2006 — and someone who works extensively with cash buyers, LLC purchases, second-home investors, and 1031 exchange clients — I believe it’s critical to stay ahead of regulatory shifts rather than react to them. This post explains: What the new rule is Who it affects What it does not change And what my role is — and isn’t — in the process

The Maui vacation rental market has gone through a meaningful reset over the past several years. After an extraordinary surge in demand and pricing during the post-pandemic cycle, the market entered a period of recalibration that tested even seasoned owners and investors. Heading into 2026, what we are seeing is not distress — but stabilization. For well-capitalized buyers and long-term investors, this phase of the cycle is beginning to look increasingly strategic. This outlook breaks down what changed, what has already been priced in, and why the next stage of the Maui vacation rental cycle may favor disciplined buyers and experienced owners.

The Maui vacation rental market continues to evolve rapidly as we move into 2026. Shifting regulations, visitor demand patterns, pricing dynamics, and buyer sentiment are reshaping how owners, investors, and property managers approach income-producing properties on the Valley Isle. In this outlook, we break down the most important forces affecting the short-term rental (STR) market — including regulatory changes, market data, and strategic considerations that matter to owners and prospective buyers alike. The Lahaina Shores Resort is one of my favorite Hotel Zoned Vacation Rental complexes in all of West Maui. The building is newly re-opened from the Aug.8, 2023 Lahaina Fires and is seeing a strong resurgence in visitor demand as well as savvy investors moving forward with new purchase. Maui Paradise Properties operates the majority of the vacation rentals at this resort and we have lots of "boots on the ground" insight we can share. Regulatory Shifts and Market Uncertainty One of the most significant drivers of the 2026 market outlook is local policy change. In late 2025, the Maui County Council advanced legislation known as Bill 9, aimed at phasing out or converting a substantial number of STR units in West and South Maui — particularly in apartment-zoned buildings — to long-term housing uses. The bill has moved through key hearings and, depending on final outcomes, could reshape the supply landscape over the next several years. Some of the latest news on Bill 9 here. These regulatory shifts create both uncertainty and opportunity: Uncertainty in supply: When thousands of units face potential rezoning or conversion, investors and owners may delay decisions until the regulatory picture becomes clearer. Opportunity in hotel-zoned and compliant inventory: Units already in hotel or similar zoning districts, or those likely to be preserved under new frameworks, may maintain higher value due to relative scarcity. Staying informed and proactive — especially regarding local policy — is essential for owners and buyers. Maintaining compliance with evolving rules helps protect asset values and ensures long-term operability. The best way to do so is to join the Hawaii Mid and Short Term Rental Alliance. Visitor Demand & Market Resilience Despite political debate and regulatory complexity, visitor demand remains a foundational driver of the Maui vacation rental market. Recent industry trend data suggest that demand for Maui STRs has stayed comparatively strong when measured by occupancy and rate metrics — with some reports showing median occupancy in the 70-80% range and average daily rates rising compared to previous years. At the same time, Maui’s status as a premier global destination continues to support the broader tourism economy. However, visitor booking behavior has become more selective, with demand influenced by pricing sensitivity, travel preferences, and overall economic context. For owners, this means that while demand remains robust, performance outcomes will increasingly differentiate based on quality, pricing strategy, and compliance with evolving regulations. Hawaii Vacation Rental Performance (State Data) Pricing Trends & Revenue Opportunities Data from industry tracking platforms indicate that Maui vacation rental average daily rates (ADR) have improved relative to previous years — but the landscape is mixed: Some segments see ADR increases due to constrained supply and strong demand in resort zones. Other segments face more pressure due to regulatory uncertainty and market segmentation.From an investment perspective, professional revenue management — including dynamic pricing and segmented demand optimization — has become more important than ever. Owners should consider partnering with operators that leverage Learn more about Maui rental ADR and occupancy trends here The blue line above represents the current paid occupancy percentage for Maui Paradise Properties and the orange indicates the Maui Market as a whole. Buyer & Owner Strategy: What This Means for You For Current Owners Review your property’s zoning status and how local legislation may affect it. Evaluate demand and rate trends for your specific resort area (Wailea, Kaanapali, Kihei, etc.). Consider revenue management tools and professional support to optimize occupancy, RevPar, and ADR. For Prospective Buyers Understand that zoning and compliance are now core due diligence components for income-producing properties. Look for properties in areas less impacted by regulatory shifts or in districts where conversion is feasible. Factor potential market shifts and demand volatility into underwriting and cash-flow modeling. Being proactive about long-range strategy — rather than reactive to market headlines — will help position buyers and owners for success. Lahaina Shores Penthouse #5 is pure eye candy and is one of my personal favorite MPP offerings at the resort. Macro & Market Context While vacation rentals face island-specific regulatory pressure, broader economic considerations continue to shape the Maui real estate and vacation rental market: Home price dynamics and inventory availability affect buyer behavior and investment timing. Tourism recovery trajectories continue to influence occupancy and pricing across lodging segments. Regulatory changes (all the way to statewide tourism policy) remain among the most consequential variables for STR performance going forward. Learn more about 2026 vacation rental trends and broader travel behavior here.

For many buyers/investors, deciding on how to rent their Maui vacation rental property parallels the importance of determining which property to purchase altogether. Much like the selection of the property, musing on the rental process namely boils down to three main facets: Cash on cash returns Personal usage and lifestyle attributes Level of service/owner involvement I frequently represent clients on these types of properties, and with this I help to guide their own decision-making process along these three distinct, yet sometimes overlapping criteria. My wife and I do operate a short term vacation portfolio within Hawaii Life but as part of my fiduciary responsibilities, I always make recommendations based on my clients' goals and what is ultimately the right fit for their personal needs. We have accepted clients and properties who are a good fit into our program, and I have referred others out to front desk programs, other independent rental programs, or have educated them about self-renting their properties. It all depends on the client’s specific needs. Here is another post to jump into now or come back to at a later time for reference: How to Properly Prepare for Owning Hawaii Vacation Rental Properties

The island of Maui has consistently been voted the #1 island in the world, hence many investors have been attracted to the numerous offerings of Maui Luxury Vacation Rental Condos located in both South Maui and West Maui; this blog post covers and ranks the very best of these properties. A common trend you will see with these resorts, they are all located either beachfront or within very short walking distance to a spectacular beach. This post only focuses on high-end short term rental condo complexes around the island that provide the ability to help offset some ownership costs with vacation rental income. All of these properties have all of the right ingredients to generate substantial annual income and are also a great home away from home. There are many spectacular properties that didn’t make this list so if don’t find something here please do reach out to me directly so that we can start identifying what will best suit your individual needs. I have in the past and am currently representing clients at a number of these fine properties and short term vacation rental transactions are my specialty please see all of my related blog posts at the end of this post. Below is the criteria by which these properties are rated on a completely subjective scale based on my own personal knowledge/experience: Exclusivity Amenities Income Potential- This metric that I am using to measure potential ROI for these properties. The ability to rent the property independently Location High-End Consistency With a total possible score of 50, I have done my best to analyze all of these properties objectively on the above mentioned criteria. I want to make clear that all of these graphs and rankings are strictly based on my professional opinion. Several of these resorts have appeared on the 2018 Conde Nast List of 25 Hawaii’s Best Resorts.