Best Vacation Rental Property Management Companies in Hawaii (2025)

Hawaii is one of the world's most aspirational vacation destinations and one of the United States' most valuable and complex short-term rental markets. Average daily rates in Hawaii's top markets are among the highest in the country. Any property owner considering operating here must understand the regulatory landscape first — the market is exceptional, but only legally compliant properties can participate. Explore Awning's Hawaii property management services to see where we operate.

Use the Airbnb estimator to model Hawaii property revenue, and check Airbnb market data for Hawaii to understand demand patterns across islands. Before listing, review the Airbnb Risk Management Playbook — Hawaii's regulatory environment makes compliance risk management especially important.

Hawaii's Vacation Rental Regulatory Environment

The regulatory situation in Hawaii is critical to understand before investing. Maui County has enacted some of the most restrictive STR regulations in the country, significantly limiting new STR permits outside of designated resort zones. Oahu (City and County of Honolulu) requires STR permits and has limited non-hosted rentals outside resort and hotel-designated zones. Kauai and the Big Island each have their own regulatory frameworks with ongoing legislative changes.

Operating a short-term rental in Hawaii without proper county permits carries significant fines. Only work with a property management company that has demonstrated compliance expertise specific to each county's regulations.

Hawaii's Major Vacation Rental Markets

Maui: Delivers the highest average daily rates of any Hawaiian island. Luxury properties in Wailea, Kaanapali, and Kapalua command exceptional rates. The post-2023 regulatory environment has significantly constrained legal STR supply, which has actually increased rates for legally compliant properties. See Maui property management →

Oahu: The most-visited Hawaiian island. The STR market is concentrated in Honolulu's resort-zone condos and limited residential permit holders. Ko Olina on the west side is a designated resort area with active STR activity.

Kauai: The Garden Isle commands premium rates for its exclusivity and natural beauty. The north shore (Hanalei, Princeville) and the south shore (Poipu) are the primary vacation rental zones. Kauai allows STRs in certain designated Visitor Destination Areas. See Kauai property management →

Big Island (Hawaii): The largest and most geographically diverse island, with markets ranging from the resort corridor of the Kohala Coast to the more bohemian Puna district.

Best Property Management Companies in Hawaii

Awning

Awning provides full-service vacation rental management in Hawaii with deep expertise in the compliance requirements that make Hawaii management uniquely complex. For mainland investors managing Hawaii properties remotely, Awning's combination of regulatory knowledge, professional operations, and AI-powered revenue management makes it a trusted partner. See all Hawaii markets →

Vacasa

Significant Hawaii presence particularly on Maui and Kauai. Strong operational infrastructure for remote island management.

Hawaii Life Vacations

A Hawaii-specific operator with presence across multiple islands, combining real estate expertise with vacation rental management. Known for luxury property management.

Hawaii STR Tools

• Airbnb estimator — Model Hawaii property revenue

• Airbnb market data — Benchmark Hawaii occupancy and ADR

• STR ROI calculator — Full investment return modeling

• Best smart locks for Airbnb — Remote access management for island properties

• Best landlord insurance — Coverage for Hawaii vacation rentals

Frequently Asked Questions

Are short-term rentals legal in Hawaii?

Short-term rentals are legal in Hawaii but subject to strict county-by-county regulations. Each island has different rules about where STRs are permitted, permit requirements, and enforcement. Operating without proper permits carries significant fines. Always verify current county regulations before operating.

What is the best Hawaiian island for vacation rental investment?

Maui produces the highest average daily rates in Hawaii, though its regulatory environment is the most restrictive for new entrants. Kauai and the Big Island's Kohala Coast offer strong markets with somewhat more accessible permit frameworks for certain property types. Consult a Hawaii-specific property manager about current permit availability before purchasing.

How much can you earn from a vacation rental in Hawaii?

Well-managed vacation rentals in Hawaii's premium markets can generate $100,000–$300,000+ in annual gross revenue for luxury properties. Condos in high-demand resort areas typically generate $60,000–$120,000 annually. Net returns depend heavily on management fees, operating costs, taxes, and financing structure.

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