Insurance & Protection
Proper Insurance
Comprehensive commercial coverage built for short-term rentals
Best Overall
The most comprehensive STR insurance — if you can stomach the premium
Contact sales • No free trial
Comparison
Proper Insurance vs Safely
Pricing, pros and cons, and buyer-fit side-by-side. Pick the one that matches your operation — or see why neither should.
Insurance & Protection
Safely
Pay-per-booking vacation rental insurance with built-in guest screening
Best for Small Hosts
Best pay-per-booking insurance for low-to-mid occupancy hosts
From $8 • No free trial
✓Editorial verdict
Which should you pick: Proper Insurance or Safely?
Pick Proper Insurance if you need comprehensive commercial coverage with no gaps — squatter protection, amenity liability, bed bug remediation, and up to $2M in general liability under one policy. 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.
Editorial perspective from the Proper Insurance side; factual claims about Safely are drawn from its review.
Pricing side-by-side
Proper Insurance
Full pricing →Contact sales • No free trial
Contact sales
Custom quotes based on property location, size, usage, and rental frequency. Industry sources indicate STR-specific commercial policies typically cost 30–50% more than standard landlord coverage. No published rate card — contact sales for a quote.
Safely
Full pricing →From $8 • No free trial
Custom
Pay-per-night model starting at $8/night; no monthly or annual commitment. Guest screening standalone is $5/check, dropping to $0.50/night when bundled with the Safely Protection Policy. Estimated annual cost $800–$1,200 per property depending on occupancy. Actual rates require a custom quote based on property count, location, and deductible choice.
What each tool does well — and where it falls short
What Proper Insurance does well
Most comprehensive STR-specific coverage on the market
Proper offers unique protections like squatter coverage, amenity liability for bikes, kayaks, and hot tubs, bed bug remediation, and commercial general liability up to $2M — endorsements most competitors simply don't carry.
Strong claims handling with dedicated specialists
Policyholders consistently report smooth, professional claims experiences. One customer noted 'everything was handled quickly, professionally, with great communication, and the whole claims process was smooth and stress-free.'
Backed by Lloyd's of London and exclusively endorsed by VRBO
The Lloyd's underwriting (A.M. Best rated 'A' Excellent) provides financial stability, while the exclusive VRBO endorsement signals deep trust from a major OTA — a distinction no other STR insurer holds.
What Safely does well
Proprietary SafelyScore database screens guests against actual vacation rental damage history
No other platform has a comparable industry-specific damage database. Screening also covers criminal databases, sex offender registries, and Interpol/Europol watchlists.
98% of claims paid in 4.5 days with sub-$1K claims within 24 hours
Operators document damage with photos and receipts — no guest confrontation required. Homeowners have up to 60 days to file.
Zero cost during vacancy with insurance fees passable to guests
Coverage activates at check-in and deactivates at check-out, eliminating traditional damage deposit friction. Operators build the fee into the nightly rate so guests effectively cover the insurance.
Where Proper Insurance falls short
Premium pricing that's hard to justify on thin margins
Multiple review sources call Proper 'one of the most expensive policies on the market.' Property managers note the premium can feel hard to justify until you actually need to file a claim.
No published pricing makes comparison shopping painful
Unlike competitors with posted rates, Proper requires a custom quote through their sales process. Operators evaluating multiple providers have to commit time to each conversation before seeing numbers.
Cancellation process can be frustrating
Some policyholders report friction when trying to cancel, particularly when taking a property off-market temporarily — a common scenario for seasonal STR operators.
Where Safely falls short
Per-night pricing compounds quickly at high occupancy
At 200+ nights/year the per-night model can exceed annual policy costs from competitors like Proper Insurance ($1,500–$2,500/year). Operators must calculate their breakeven.
Does not replace homeowners insurance and has meaningful coverage exclusions
Excludes weather damage, non-guest-caused damage, fine art and collectibles. Contents theft/damage caps at $10,000 and there is a 90-day maximum consecutive rental period.
Limited public reviews and relatively new market presence
Compared to established insurers like Proper Insurance or CBIZ, Safely has fewer independent user reviews, making real-world claims experience harder to assess at scale.
Which should you pick
Pick Proper Insurance if
Large portfolio hosts needing comprehensive commercial coverage with specialized STR protections like squatter situations and amenity liability.
Skip Proper Insurance if
Budget-conscious operators or hosts with minimal rental activity seeking basic coverage.
Pick Safely if
Seasonal or part-time hosts renting fewer than ~100 nights/year who want insurance and guest screening bundled without an annual commitment — the pay-per-booking model keeps costs proportional to actual occupancy.
Skip Safely if
You run high-occupancy properties at 250+ nights/year — per-night pricing will exceed annual policy alternatives, and coverage caps ($10K contents, no weather damage) may be insufficient for premium properties.
Where Proper Insurance and Safely actually differ
- Proper offers commercial general liability up to $2M; Safely's primary commercial coverage caps at $1M with a $10K contents limit.
- Proper is a standalone commercial policy; Safely is supplemental coverage that does not replace homeowners insurance and excludes weather damage, fine art, and stays beyond 90 days.
- Proper includes squatter-situation coverage, amenity liability (pools, hot tubs, bikes, kayaks), and bed bug remediation — none of which Safely covers.
- Safely uses pay-per-night pricing starting at $8/night with zero cost during vacancy; Proper requires a custom-quoted annual policy with no published rates.
- Safely bundles guest screening via its proprietary SafelyScore damage-history database; Proper is pure insurance with no guest-screening component.
Common objections
- Safely's per-booking model means I only pay when I have guests — why commit to an annual Proper policy?
- The per-night model works in your favor below roughly 100–150 nights per year. Above that, Safely's costs compound past what an annual Proper policy would run, and you're still carrying a less comprehensive policy with a $10K contents cap and no coverage for squatters or amenity liability.
- Safely includes guest screening — doesn't that reduce risk enough to justify lighter coverage?
- Guest screening helps prevent damage, but it can't prevent every incident and does nothing for liability claims from guest injuries, squatter situations, or bed bug outbreaks. Proper covers the risks that screening can't eliminate.
- Proper has no published pricing and requires a sales call — how do I know it's worth the hassle?
- It's a legitimate friction point. But if you manage 5+ properties or have amenities like hot tubs and pools, the coverage gap between Safely's supplemental policy and Proper's full commercial policy is wide enough that one uninsured claim could cost more than years of premiums. The sales call is worth the 20 minutes.
Keep digging
Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium
Safely
Best pay-per-booking insurance for low-to-mid occupancy hosts