Insurance for multi-property STR portfolio: bundle strategies and cost reduction

Category: Multi-Property & Scaling

By: James Wu

Posted: 2026-02-03T19:54:33.147Z

I'm paying insurance separately for each of my 5 STR properties and it's costing me over $8,000/year total. Each property has its own policy with different companies. Is there a way to bundle STR insurance across multiple properties for a discount? Are there portfolio insurance options? What strategies do multi-property owners use to reduce insurance costs?

Reply by Kevin O'Brien:

Insurance for a portfolio of 5+ properties should absolutely be bundled. Here's how to reduce costs: **Portfolio/blanket policies:** Several STR-focused insurers offer portfolio pricing: 1. **Proper Insurance** (https://properinsurance.com) — They offer multi-property discounts. 3+ properties typically get 10-15% off per-property rates. 5+ properties: 15-20% off. Call them directly for portfolio pricing (don't just quote online). 2. **CBIZ** — Commercial insurance broker that bundles STR properties under a single policy. Better for 5+ properties. Single deductible, single premium, simplified claims. 3. **Safely** (https://safely.com) — Per-booking model. At your scale, switching to per-booking pricing might actually be cheaper if your average occupancy is under 70%. Math: 200 bookings/year × $6/booking = $1,200 vs $1,600 for an annual policy on one property. 4. **Steadily** (https://steadily.com) — Good portfolio rates, fast online quoting. Compare them against Proper for each property. **Cost reduction strategies:** 1. **Higher deductibles.** Going from $1,000 to $2,500 deductible can save 15-25% on premiums. With 5 properties and good maintenance, you shouldn't be filing claims often. Higher deductible = lower premium. 2. **Bundled umbrella.** Instead of increasing per-property liability, get one personal umbrella ($2M coverage for ~$300-400/year) that extends over all properties. Cheaper than increasing each policy independently. 3. **Annual review.** Insurance rates change. Get re-quoted every January. I switch carriers every 2-3 years because the "new customer" rate is always better than the renewal rate. 4. **Loss prevention discounts:** - Smart locks (documented) = some carriers discount 5% - Security cameras (exterior, disclosed) = 5% - Smoke + CO detectors (verified) = 5% - Minut noise monitoring = some carriers recognize this - Fire extinguishers = 2-3% - Water leak sensors = up to 5% 5. **Form an LLC** and insure the LLC (not personal). Commercial policies for LLCs can be cheaper than personal policies for the same coverage. **My portfolio insurance stack (5 properties):** - Proper Insurance portfolio policy: $5,200/year (saves $2,800 vs individual policies) - Personal umbrella ($2M): $350/year - **Total: $5,550/year** for full coverage across all properties That's $1,110/property/year = $92/month. At my revenue levels, insurance is about 3.5% of gross — well worth the protection.