Proper Insurance Alternatives
Looking past Proper Insurance? Here’s how the main alternatives compare on pricing, fit, and verdict.
For context: Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium
Contact sales • No free trial
Main alternatives
Same category, different fit. Each card uses pair-specific comparison notes.
- Compare vs Proper Insurance →Awning InsuranceSolid Option
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.
- Pricing
- From $40 • No free trial
- Compare vs Proper Insurance →SafelyBest for Small Hosts
Pick Safely if you're a low-occupancy or seasonal host who wants pay-per-booking pricing and bundled guest screening without an annual commitment.
- Pricing
- From $8 • No free trial
Pick 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.
- Pricing
- Contact sales • No free trial
- Compare vs Proper Insurance →InsuraGuestBest Value
STR 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.
- Pricing
- From $69 • No free trial
How to pick between them
- Count your listings first. Most STR property management pricing scales per-listing or per-tier. The right tool at 3 listings is often the wrong one at 30.
- Do booking fees matter to you? A 1% fee on $200k/yr of direct bookings is $2,000/yr. That can flip the math.
- List the non-negotiable integrations. Your dynamic pricing tool, cleaning platform, and smart locks all need to connect. Confirm before committing.
- Free trial or demo only? Some vendors let you touch the product. Others only show it on a sales call. If trialing matters to you, that filters fast.
Decided Proper Insurance is still the right fit?
Build your stack
Need more than a Proper Insurance alternative?
Use the stack-builder to choose the PMS, pricing, cleaning, guest messaging, and direct-booking pieces that fit together before you evaluate a single vendor.