Best Overall
Last updated 2026-04-20Proper Insurance for mid-sized portfolios (5–20 listings)
Operators at 5–20 listings, past the solo-host stage but not yet running a full property management company.
Our verdict for mid-sized portfolios (5–20 listings)
Great fit
This is Proper's sweet spot — enough units to spread the premium cost, enough risk exposure to need the specialized coverage.
Why it fits you
- Amenity liability and squatter coverage become real risks as your portfolio diversifies
- Commercial general liability up to $2M protects against the catastrophic scenarios that grow more likely at scale
- Dedicated claims specialists mean you're not fighting an automated system when something goes wrong
What might bite you
- Still expensive — run the numbers against competitors like Safely or Awning to confirm the coverage delta justifies the price
Best-for-you alternatives at this size
- Safely Okay fit — consider alternatives
Safely can work across a 10–30 unit portfolio, but run the occupancy math — per-night pricing may exceed annual alternatives at 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?
Contact sales • No free trial