Hawaii Vacation Rental Management Companies: The 2026 Market in Numbers
We pulled every Hawaii member of the national vacation rental managers’ association and ranked the market by the numbers: how many companies, who manages the most units, how concentrated it is, and what software runs it.
Hawaii is home to 106 VRMA-member vacation rental management companies, of which 45 disclosed a unit count totaling 6,077 managed units. The market is best described as an island-by-island, resort-condo market.
The largest reporting operator is Castle Resorts & Hotels at roughly 1,000 units. The top five reporting operators control about 51 percent of all units disclosed, the most common property management system among members is HomeAway / Escapia (legacy), and the median member company was founded around 2008.
01Hawaii at a glance
VRMA member companies headquartered in Hawaii, March 2026.
02The largest operators
Ranked by self-reported units managed. Figures are disclosed by the operators themselves.
| # | Operator | Units (self-reported) |
|---|---|---|
| 1 | Castle Resorts & HotelsHonolulu | 1,000 |
| 2 | Outrigger Resorts & HotelsHonolulu | 880 |
| 3 | AA Oceanfront Rentals and SalesKihei | 500 |
| 4 | CONDOMINIUM RENTALS HAWAIIKIHEI | 375 |
| 5 | The Parrish Collection LLCKoloa | 350 |
| 6 | My Perfect Stays LLCLahaina | 330 |
| 7 | Rentals Maui IncKihei | 320 |
| 8 | Kona Coast VacationsKailua Kona | 280 |
| 9 | Elite Pacific PropertiesHonolulu | 205 |
| 10 | Chase N Rainbows Real Estate Inc.Lahaina | 205 |
03How concentrated is the market?
The five largest reporting operators control about 51 percent of every unit disclosed by Hawaii members. That is a middle-of-the-road split typical of established markets.
04What software runs the market
Most-named property management systems among Hawaii members.
According to the VRMA directory, the unit-heavy incumbents in Hawaii still lean on Streamline and legacy HomeAway/Escapia systems, the same generational pattern we documented across the whole industry in the PMS market analysis.
05What the data says
Hawaii is an island-by-island market dominated by resort-condominium operators. According to the VRMA public member directory (compiled March 2026), 106 Hawaii companies are members. After excluding Marina Hawaii Vacations (see below), the largest reporting short-term rental operator is Castle Resorts & Hotels at roughly 1,000 units, followed by Outrigger Resorts & Hotels.
The inventory is concentrated on Oahu's Waikiki, Maui, Kauai, and the Big Island, and it skews toward condo-resort buildings rather than detached homes. That shows up in the software: legacy HomeAway and Escapia systems, built for large repeatable condo inventories, are the most common here, unlike the Streamline-led mainland markets. The median Hawaii member was founded around 2008, the oldest cohort of any state we mapped.
06Compare other states
Figures come from RapidEye's analysis of the VRMA (Vacation Rental Management Association) public member directory, compiled March 2026. Counts cover companies that list a Hawaii headquarters. Unit counts are self-reported; only 45 of 106 Hawaii members disclosed one, so the 6,077-unit total is a floor, not a census of every short-term rental in the state.
We de-duplicated companies that appear under multiple brand spellings (keeping the higher figure) and excluded entries whose self-reported totals reflect national franchise networks, timeshare or HOA portfolios, or brands since acquired and folded into a national operator. In Hawaii, the largest excluded entry was Hawaiian Properties, Ltd. dba Marina Hawaii Vacations (35,840 self-reported units), a residential and HOA portfolio, not short-term rentals.
07Sources
- VRMA (Vacation Rental Management Association) — Public Member Directory, compiled March 2026 (primary data set).https://www.vrma.org/search/newsearch.asp
- RapidEye — The Largest Short-Term Rental Management Companies (2026).https://rapideyeinspections.com/blog/largest-short-term-rental-management-companies/
- RapidEye — The Vacation Rental PMS Market Just Flipped: 40 Years in One Chart.https://rapideyeinspections.com/blog/vacation-rental-pms-generational-shift/
08Frequently asked
How many vacation rental management companies are in Hawaii?
According to the VRMA public member directory compiled in March 2026, Hawaii has 106 member vacation rental management companies. Of those, 45 disclosed a unit count, together reporting 6,077 managed units.
Who is the largest vacation rental management company in Hawaii?
Based on self-reported figures in the VRMA directory, the largest reporting operator in Hawaii is Castle Resorts & Hotels with approximately 1,000 units. The five largest reporting operators together account for about 51 percent of all units disclosed by Hawaii members.
What property management software do Hawaii vacation rental companies use?
Among Hawaii members that named a property management system, HomeAway / Escapia (legacy) is the most common, consistent with the broader pattern in which Streamline and legacy HomeAway/Escapia systems still run most unit-heavy incumbents.