Proper 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
- Awning Insurance Okay fit — consider alternatives
Useful as a benchmark check against your incumbent carrier, but not a portfolio management tool — you'll still bind directly with one of the four partners.
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 Okay fit — consider alternatives
Mid-portfolio owners can get coverage, but CBIZ doesn't publish portfolio-level minimums or multi-property discounts, so you'll need to negotiate via the quote process.
Contact sales • No free trial · Established specialty STR insurer — but you'll need to call for a quote
- InsuraGuest Okay fit — consider alternatives
Blanket coverage across a portfolio is convenient, but property-manager pricing isn't publicly published — you'll need to ask for a rate card.
From $69 • No free trial · Affordable flat-rate guest protection layer for PMS-connected operators
Still think Proper Insurance is right for you?
Contact sales • No free trial