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 InsuraGuest
Pricing, pros and cons, and buyer-fit side-by-side. Pick the one that matches your operation — or see why neither should.
Insurance & Protection
InsuraGuest
Flat-rate guest damage and accidental medical coverage for short-term rentals
Best Value
Affordable flat-rate guest protection layer for PMS-connected operators
From $69 • No free trial
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.
Try Proper InsuranceInsuraGuest
Full pricing →From $69 • No free trial
Basic
$69/mo
- Up to $10,000 property damage coverage
- $100 deductible on property damage
- Accidental medical benefit for guest injuries
Plus
$99/mo
- Up to $25,000 medical benefit
- Higher coverage maximum
- Same no-fault, first-payor claims model
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 InsuraGuest does well
Most claims paid within 72 hours on a no-fault model
The vendor advertises 72-hour payouts and a 'first-payor' approach where claims are handled regardless of who's responsible, reducing guest dispute friction during a stay.
Guest-fee pass-through built into the workflow
Operators can recover the subscription cost as a ~$3/day add-on through their PMS or OTA (Airbnb, VRBO, Booking.com), effectively zeroing out the line item.
Pre-integrated with the major STR PMS platforms
Rather than custom plumbing, InsuraGuest ships pre-built integrations with Hostaway, Hostfully, Guesty, Lodgify, OwnerRez, Tokeet, Track, and others.
Predictable flat-monthly subscription
Unlike percentage-of-booking insurance products, InsuraGuest charges a single flat fee per account regardless of nights booked or portfolio revenue.
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 InsuraGuest falls short
Coverage caps are modest for higher-end portfolios
The top tier maxes out at $25,000 — fine for typical guest mishaps, but light for luxury homes or larger damage scenarios where a true high-limit per-occurrence policy would be more appropriate.
Mixed third-party reviews on claims responsiveness
While the vendor markets 72-hour payouts, independent comparison content from Uplisting notes inconsistent host-side experience and limited host-specific testimonials.
Property-manager-program pricing is opaque
The public site advertises individual host tiers but does not publish a transparent rate card for multi-property managers or PMS-channel deals.
It's an add-on, not a replacement
InsuraGuest is positioned as a layer on top of existing insurance — operators still need underlying landlord/structural property coverage and any high-limit liability separately.
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 InsuraGuest if
STR operators on a connected PMS (Hostaway, Hostfully, Guesty) who want a low-flat-rate guest-damage and accidental-medical layer they can pass through to guests as a nightly fee.
Skip InsuraGuest if
You need full structural/landlord property insurance, high-limit liability above $25K, or carrier-of-record protection — InsuraGuest is a layer, not a replacement.
Keep Digging
Proper Insurance
The most comprehensive STR insurance — if you can stomach the premium
InsuraGuest
Affordable flat-rate guest protection layer for PMS-connected operators