Proper Insurance for large portfolios (20–100 listings)
Professional operators and small-to-mid property management companies running 20–100 listings, typically with dedicated staff and systems.
Our verdict for large portfolios (20–100 listings)
Great fit
At 20+ listings the odds of needing specialized coverage approach certainty — Proper's breadth pays for itself the first time you file a non-standard claim.
Why it fits you
- Squatter situations, bed bug remediation, and amenity liability are portfolio-level risks that standard policies exclude
- 100,000+ policyholder base means the underwriting model is battle-tested at scale
- VRBO exclusive endorsement signals deep industry trust
What might bite you
- No volume discount transparency — you'll need to negotiate directly and may not get the rate visibility larger operators expect
Best-for-you alternatives at this size
- Safely Okay fit — consider alternatives
Pay-per-booking math works at high nightly-rate properties but gets expensive at 250+ nights/yr/property. Large operators running high-occupancy urban or resort units often do better with annual policies like Proper or Steadily at this scale.
From $8 • No free trial · Best pay-per-booking insurance for low-to-mid occupancy hosts
- Awning Insurance Consider alternatives
Awning's curated four-carrier set is consumer-facing residential STR; large portfolios with mixed property types should engage a specialized commercial broker directly.
From $40 • No free trial · Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
- CBIZ Vacation Rental Insurance Consider alternatives
CBIZ is positioned for owner-hosts of 1–4-unit properties, not large multi-property managers — research confirmed eligibility caps around 1–4 units per policy.
Contact sales • No free trial · Established specialty STR insurer — but you'll need to call for a quote
Still think Proper Insurance is right for you?
Contact sales • No free trial