Massachusetts has the highest median portfolio and lowest skew of any state in the VRMA data. This market is uniformly professionalized.
We analyzed the 54 VRMA member vacation rental companies headquartered in Massachusetts. Only 20 reported unit counts, but what they show is distinctive: a median of 103 units, a mean of 156, and a mean-to-median ratio of just 1.5x. No other state comes close to this level of uniformity. Nearly the entire market runs through Cape Cod and the Islands. This only covers VRMA members, not individual hosts or non-member companies.
skew (lowest)
in Massachusetts
company (highest in US)
20 reporting companies
(one of the oldest)
A 1.5x skew means the big players aren't that much bigger
Mean-to-median skew measures how much the largest operators distort the average. In most states, a few mega-operators push the mean far above the median. According to VRMA's public member directory (compiled March 2026), Massachusetts is the exception. Its 1.5x ratio means the mean is only 50% higher than the median. For comparison, Florida's ratio is 2.6x and Texas runs at 3.0x. The practical implication: there is no dominant mega-operator in Massachusetts pulling the distribution. The market is a cluster of similarly-sized professional managers.
Cape Cod and the Islands are the entire market
Massachusetts vacation rental management is concentrated in a tight geographic band: the Cape Cod towns (Chatham, Orleans, Brewster, Dennis Port), Martha's Vineyard (Edgartown, Vineyard Haven), and Nantucket. Boston appears in the data with 6 companies, but it's a different business: urban short-term rental management rather than resort-style vacation rentals. According to the VRMA member directory, the Cape and Islands account for the overwhelming majority of reported units.
A market without a missing middle
Most states show a bimodal pattern: a mass of small operators (under 25 units) and a handful of large ones (250+), with a hollow middle. Massachusetts is different. Six companies sit in the 101-250 range, managing 1,134 units between them. The middle tiers are populated. Of the 20 companies that reported, only 7 manage 10 or fewer units. The 1-10 bracket that dominates other states is a minority here.
Streamline and Barefoot run Massachusetts
Among the 18 Massachusetts VRMA members who reported their PMS, Streamline leads with 6 companies (33.3%). Barefoot follows with 3 (16.7%). This two-platform dominance reflects the market's maturity: both Streamline and Barefoot are legacy platforms favored by established resort-area managers. The remaining PMS choices are scattered across HomeAway, Hostfully, LiveRez, and various "Other" selections. According to the VRMA directory, no modern entrants like Guesty or Hostaway have meaningful presence here.
The 15 largest VRMA members in Massachusetts
Self-reported unit counts from VRMA membership profiles. Only 20 of 54 Massachusetts members reported a portfolio size. Sandpiper Rentals has led the market from Martha's Vineyard since 1969. The top 4 companies alone account for 1,776 of the state's 3,115 reported units (57%). Note the founding dates: 1969, 1980, 2001, 2002. This is an old market.
| # | Company | City | Units | PMS | Founded |
|---|---|---|---|---|---|
| 2 | Kinlin Grover Compass | Brewster | 501 | Barefoot | 1980 |
| 3 | Del Mar Vacations | Orleans | 350 | Streamline | 2015 |
| 4 | Point B Realty | Vineyard Haven | 275 | Streamline | 2009 |
| 5 | Martha Murray Vacation Rentals | Dennis Port | 250 | - | - |
| 6 | New England Vacation Rentals | Chatham | 230 | Streamline | 2001 |
| 7 | South End Hospitality | Jamaica Plain | 225 | Other | 2014 |
| 8 | Pretty Picky Properties | Brewster | 199 | Streamline | 2002 |
| 9 | oldCape Sotheby's | Orleans | 125 | HomeAway | 2002 |
| 10 | Maverick Suites | Boston | 105 | Other | 1998 |
| 11 | Leighton Rentals | South Dennis | 100 | Streamline | 2003 |
| 12 | Niagara Hospitality | Boston | 35 | - | - |
| 13 | InsideOut Properties | N Eastham | 26 | Hostfully | 2019 |
| 14 | Good People Property Mgmt | Sudbury | 10 | Other | 2016 |
| 15 | The Vineyard Life | Edgartown | 9 | Streamline | 2017 |
The median founding year of 2005 makes Massachusetts one of the oldest professional VR markets in VRMA data. But the real story is deeper: Sandpiper Rentals dates to 1969, Kinlin Grover to 1980. These aren't tech-enabled startups that discovered Airbnb. They're property management businesses that predate the internet, built around families renting the same Cape house every August.
That history explains the uniform professionalization. When operators have been in the market for 20-50 years, the small ones either grew or exited. What remains is a stable cohort of mid-to-large managers with similar operational maturity.
That's the highest bar of any state. In Florida, the median is 33. In Texas, it's lower still. Massachusetts operators compete against a field of established, similarly-sized professionals. There's no long tail of hobbyist managers to differentiate against.
The operational implication: efficiency and quality are the only differentiators. You can't outgrow your way past competitors who have been here for decades. The companies that win in this market do it through better processes, better technology adoption, and better guest experience on every single turnover.
Sources
- VRMA (Vacation Rental Management Association) Public Member Directory. Self-reported company data including unit counts, PMS, founding year, HQ city, and operating states. Compiled March 2026. 54 member companies headquartered in Massachusetts; 20 reported unit counts. https://www.vrma.org/directories/vacation-rental-managers