Best Overall
Last updated 2026-04-20Proper 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
Still think Proper Insurance is right for you?
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