STR Insurance & Damage Protection

Premium STR policy

Proper Insurance

Purpose-built short-term-rental insurance underwritten by Lloyd's of London — covers what a homeowner's policy refuses to.

Best for

US owner-operators of one or more STR properties who want comprehensive replacement-cost coverage and high liability limits.

Pricing

Custom annual premiums; typically $1,500–$3,500 per year per property depending on value and market.

HQ & founded

Whitefish, Montana, USA · 2017

• Building, contents, liability, and business income in one policy
• Up to $2M liability and $1M in contents replacement
• Covers commercial use that homeowner policies explicitly exclude
• Underwritten by Lloyd's of London syndicates

Cavmir take: The premium pick. Annual premium is meaningful but the coverage gap between this and a homeowner policy at claim time is enormous.

Online STR & landlord

Steadily

Online-first landlord and STR insurance — instant quote, fully digital onboarding, designed for modern hosts.

Best for

Owners who want a fast no-broker quote and a defensible STR-aware policy at a competitive annual price.

Pricing

Custom; often 20–40% under Proper for comparable coverage. Quote in minutes online.

HQ & founded

Austin, Texas, USA · 2020

• STR, long-term rental, and landlord policies under one carrier
• Instant online quote — no broker call required
• Property + liability + loss-of-rent coverage
• A-rated carrier panel including Lloyd's syndicates

Cavmir take: Where most owners actually start. Worth quoting Steadily and Proper side-by-side at every renewal — the gap can move by hundreds per year.

Investor-focused

Obie

Tech-forward landlord and STR insurance built for property investors — instant quotes, lender-accepted certificates, portfolio-level pricing.

Best for

Investors with multiple properties or financed portfolios where lenders require fast certificates of insurance.

Pricing

Online quote in minutes; pricing competitive with Steadily, often more negotiable at portfolio scale.

HQ & founded

Chicago, Illinois, USA · 2017

• Online quote and bind for single or multi-property portfolios
• Lender-required COIs in minutes, not days
• STR, multifamily, and single-family residential under one platform
• a16z-backed; rapid product roadmap

Cavmir take: The right pick when there's a lender on the line. Often beats Steadily on portfolio pricing once you cross 3–5 properties under one borrower.

International + screening

SUPERHOG

Global guest screening + per-stay damage protection — covers gaps where US carriers won't write a policy.

Best for

International owners (Latin America, Europe, Asia) and any portfolio where Proper, Steadily, or Obie don't operate.

Pricing

Per-booking model; typically $5–$15 per stay depending on cover and verification level.

HQ & founded

Northampton, United Kingdom · 2019

• Identity and payment-fraud screening on every booking
• Up to $5M in damage protection per stay
• Global coverage — works wherever the property sits
• Integrates with Airbnb, Vrbo, Booking.com, and major PMSs

Cavmir take: The de-facto international option. Especially relevant for our Brazil, Caribbean, and EU clients where US-only carriers don't apply.

Per-stay damage waiver

Safely

Per-stay damage waiver layered on top of your annual policy — pre-screens guests and pays out fast on covered claims.

Best for

Hosts who already carry annual insurance but want a faster, cleaner damage-claim path than the OTA AirCover route.

Pricing

Per-stay fee, typically passed through to the guest as part of the cleaning or service charge.

HQ & founded

Atlanta, Georgia, USA · 2015

• Background and identity check on every booking
• Up to $1M in property damage protection per stay
• Up to $1M in liability coverage
• Faster claims process than Airbnb AirCover

Cavmir take: Not a substitute for a real annual policy — pair it with Proper, Steadily, or Obie. Useful when an OTA-handled claim drags on or gets denied.