All tools/Proper Insurance
Comprehensive commercial coverage built for short-term rentals
At a glance
Updated 2026-04-20The most comprehensive STR insurance — if you can stomach the premium
Best for: Portfolio hosts who want the broadest possible STR coverage and are willing to pay a premium for specialized protections like squatter and amenity liability
Pricing
Contact sales • No free trial
Proper Insurance is the largest STR-specific insurer in the United States, offering commercial general liability and property coverage purpose-built for Airbnb, Vrbo, and vacation rental owners. Underwritten by Lloyd's of London (A.M. Best rated 'A' Excellent), Proper covers unique STR risks — squatter situations, amenity liability, bed bugs, and more — that standard homeowner or landlord policies exclude.
Honest per-segment take. Click any card for the full breakdown.
1–5 listings
Proper's coverage is best-in-class, but the premium pricing hits harder when you only have 1–5 units absorbing the cost.
Read full take →
5–20 listings
This is Proper's sweet spot — enough units to spread the premium cost, enough risk exposure to need the specialized coverage.
Read full take →
20–100 listings
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.
Read full take →
Airbnb primary
Proper fills the gaps Airbnb's Host Protection leaves wide open, but you're paying a premium for coverage breadth you may not fully need on a single platform.
Read full take →
Vrbo primary
Proper is VRBO's exclusively endorsed insurance provider — if you're VRBO-first, this is the default choice for a reason.
Read full take →
3+ channels
Multi-channel hosts face the widest range of liability scenarios — Proper's coverage breadth matches that exposure better than any competitor.
Read full take →
Same category, different fits. Each pick has a direct comparison reason.
Pick Awning Insurance if you want a one-page triage of four STR carriers (Proper, Obie, Toggle, Hippo) with published price floors before committing to any single quote process.
From $40 • No free trial
View alternativesPick Safely if you're a low-occupancy or seasonal host who wants pay-per-booking pricing and bundled guest screening without an annual commitment.
From $8 • No free trial
View alternativesPick CBIZ if you're a single-property or small-portfolio owner-host (1–4 units) who wants a straightforward bundled commercial policy from a broker with 20+ years in the vacation-rental niche.
Contact sales • No free trial
View alternativesSTR operators on a connected PMS who want a low-flat-rate guest-damage and accidental-medical layer they can pass through as a guest fee.
From $69 • No free trial
View alternativesStay in the loop
Sign up for new comparisons and practical notes on your rental software stack.
Planning your setup? Get the STR tech stack checklist →