Short-term rental insurance: Safely vs Steadily vs CBIZ vs Proper

Category: Legal & Regulations

By: James Wu

Posted: 2025-12-04T20:51:24.252Z

I need dedicated STR insurance but I'm drowning in options. Currently I have a standard homeowner's policy which my agent says probably won't cover STR-related claims. Has anyone compared the STR-specific insurance providers? What coverage matters most?

Reply by Anika Sharma:

STR insurance is one of the most important (and overlooked) business expenses. Here's my comparison: **Safely (https://safely.com)** - Per-reservation pricing model (no annual premium) - $1M liability per booking - Guest damage protection up to $10K - Automatic guest screening - Best for: Hosts who want coverage that scales with bookings - Cost: $8-15 per reservation depending on property value **Steadily (https://steadily.com)** - Annual policy (traditional insurance model) - $1M+ liability coverage - Property damage, theft, loss of income - Covers direct bookings and OTA bookings - Best for: Hosts who want comprehensive year-round coverage - Cost: $1,500-3,000/year depending on property **CBIZ (Vacation Rental Insurance)** - Annual policy, established carrier - Comprehensive property and liability coverage - Business interruption coverage - Best for: Higher-value properties and multi-property portfolios - Cost: $2,000-5,000/year **Proper Insurance** - Annual policy specifically for STR - Commercial-grade coverage - Covers both hosted and un-hosted stays - Best for: Hosts who also do mid-term rentals or have on-site staff - Cost: $2,500-6,000/year **What coverage matters most:** 1. **Liability** ($1M minimum) — guest injury claims can be devastating 2. **Property damage** — beyond what AirCover covers 3. **Loss of income** — if your property is damaged and can't host 4. **Direct booking coverage** — many policies only cover OTA bookings 5. **Bed bug treatment** — seriously, check for this. It's a $2K-5K expense that many policies exclude. **My setup:** Steadily annual policy + Safely per-reservation for the guest screening/damage component. Belt AND suspenders. Total cost ~$3K/year which is about 2-3% of revenue.

Reply by Lauren Fischer:

One critical tip: READ YOUR EXISTING HOMEOWNER'S POLICY. Most standard homeowner's policies have a "business activity exclusion" that voids your entire policy (not just STR claims) if you're running an STR without disclosure. I know a host whose water heater flooded their house. Insurance denied the $80K claim because they found Airbnb listings tied to the address. The STR activity voided the entire policy, even though the flood had nothing to do with guests. Get proper STR insurance. Don't risk your homeowner's coverage.