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All tools/Awning Insurance

Solid Option
How we reviewBy STRStack · Last updated 2026-04-26

Awning Insurance for small portfolios (1–5 listings)

Hosts with 1–5 short-term rental listings looking for software that scales with them, not against them.

Our verdict for small portfolios (1–5 listings)

Great fit

If you're a new Airbnb host evaluating your first STR policy, Awning's one-page comparison of four named carriers is exactly the triage tool you want.

Why it fits you

  • Published price floors ($40 Obie, $100 Proper) let you bracket cost expectations before quoting
  • Obie quote completes in under 5 minutes alongside Awning's Airbnb income estimator
  • Carrier-by-carrier positioning explains who fits which property profile

What might bite you

  • Awning is a broker, so claims experience depends on the underlying carrier you bind with

Best-for-you alternatives at this size

  • If you're an individual owner of a single STR or a small portfolio of 1–4-unit properties, CBIZ is purpose-built for you — it's the segment they explicitly target.

    Contact sales • No free trial · Established specialty STR insurer — but you'll need to call for a quote

  • InsuraGuest Great fit

    If you've got 1–5 listings on a connected PMS, $69/mo flat for guest damage and medical coverage is hard to beat — and you can pass it through as a nightly fee.

    From $69 • No free trial · Affordable flat-rate guest protection layer for PMS-connected operators

  • Safely Great fit

    Safely's pay-per-night model is built for you — zero cost during vacancy, no annual commitment, and guest screening bundled in.

    From $8 • No free trial · Best pay-per-booking insurance for low-to-mid occupancy hosts

Still think Awning Insurance is right for you?

From $40 • No free trial