Massachusetts Vacation Rental Management Companies: The 2026 Market in Numbers
We pulled every Massachusetts 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.
Massachusetts is home to 50 VRMA-member vacation rental management companies, of which 20 disclosed a unit count totaling 3,115 managed units. The market is best described as a concentrated, operator-led market.
The largest reporting operator is Sandpiper Rentals, Inc. at roughly 650 units. The top five reporting operators control about 65 percent of all units disclosed, the most common property management system among members is Streamline, and the median member company was founded around 2005.
01Massachusetts at a glance
VRMA member companies headquartered in Massachusetts, March 2026.
02The largest operators
Ranked by self-reported units managed. Figures are disclosed by the operators themselves.
| # | Operator | Units (self-reported) |
|---|---|---|
| 1 | Sandpiper Rentals, Inc.Edgartown | 650 |
| 2 | Kinlin Grover Compass Vacation RentalsBrewster | 501 |
| 3 | Del Mar VacationsOrleans | 350 |
| 4 | Point B Realty, LLCVineyard Haven | 275 |
| 5 | Martha Murray Vacation RentalsDennis Port | 250 |
| 6 | New England Vacation Rentals Inc.Chatham | 230 |
| 7 | South End HospitalityJamaica Plain | 225 |
| 8 | Pretty Picky PropertiesBrewster | 199 |
| 9 | oldCape Sotheby's International RealtyOrleans | 125 |
| 10 | Maverick SuitesBoston | 105 |
03How concentrated is the market?
The five largest reporting operators control about 65 percent of every unit disclosed by Massachusetts members. That is unusually concentrated, the mark of a resort-anchored market.
04What software runs the market
Most-named property management systems among Massachusetts members.
According to the VRMA directory, the unit-heavy incumbents in Massachusetts 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
According to the VRMA public member directory (compiled March 2026), Massachusetts has 50 member vacation rental management companies, of which 20 disclosed a unit count totaling 3,115 managed units. The largest reporting operator is Sandpiper Rentals, Inc. at roughly 650 units, and the top five reporting operators hold about 65 percent of disclosed units, making Massachusetts unusually concentrated for its size.
Most Massachusetts members are small independents rather than large portfolio operators; the median member company was founded around 2005. Among members that named a property management system, Streamline is the most common, consistent with the broader industry pattern in which Streamline and legacy HomeAway and Escapia systems still run most unit-heavy incumbents.
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 Massachusetts headquarters. Unit counts are self-reported; only 20 of 50 Massachusetts members disclosed one, so the 3,115-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. Massachusetts required only standard de-duplication; no national-franchise, timeshare, or HOA totals needed to be removed.
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 Massachusetts?
According to the VRMA public member directory compiled in March 2026, Massachusetts has 50 member vacation rental management companies. Of those, 20 disclosed a unit count, together reporting 3,115 managed units.
Who is the largest vacation rental management company in Massachusetts?
Based on self-reported figures in the VRMA directory, the largest reporting operator in Massachusetts is Sandpiper Rentals, Inc. with approximately 650 units. The five largest reporting operators together account for about 65 percent of all units disclosed by Massachusetts members.
What property management software do Massachusetts vacation rental companies use?
Among Massachusetts members that named a property management system, Streamline is the most common, consistent with the broader pattern in which Streamline and legacy HomeAway/Escapia systems still run most unit-heavy incumbents.