Insurance & Protection
Awning Insurance
Curated STR insurance marketplace surfacing four vetted carriers
Solid Option
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
From $40 • No free trial
Comparison
Awning 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
Awning Insurance
Full pricing →From $40 • No free trial
Obie
From $40/mo
- Budget-friendly part-time and full-time host coverage
- Quote completion in under 5 minutes via Awning estimator integration
Proper
From $100/mo
- Airbnb-native integration with flexible coverage
- Fast underwriting; positioned as the most popular STR carrier
Toggle
Custom (high-value properties)
- Custom limits up to $2M+ for luxury vacation rentals
- White-glove claims service
Hippo
Competitive (bundled)
- Combined homeowners + STR coverage under one policy
- Digital-first claims for part-time rental hosts
InsuraGuest
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 Awning Insurance does well
Four named STR carriers compared on one page
Awning surfaces Proper, Obie, Toggle, and Hippo with one-line positioning each, cutting the search-and-compare burden for buyers who don't already know the STR-insurance landscape.
Transparent price anchors instead of contact-sales gating
The marketplace publishes 'rates starting at just $40/month' for Obie and 'From $100/month' for Proper, plus an affordability bracket noting most hosts pay $100–$200/mo for comprehensive coverage.
Obie quote bundled into the Airbnb estimator workflow
For investors already using Awning's Airbnb income estimator, the Obie partnership lets them request a quote in under 5 minutes from inside the same workflow used to underwrite the property.
Clear carrier-by-carrier positioning
Toggle is steered to high-value/luxury (custom limits up to $2M+), Hippo to bundled homeowners+STR, Obie to budget, and Proper to Airbnb-native — useful triage without reading four carrier sites.
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 Awning Insurance falls short
Awning is a broker, not the carrier
Claims, renewals, and underwriting run through whichever partner carrier you bind with. Awning's own roundups describe its row as 'Coverage Limit: Varies' and the unique feature as 'Integrated with PM platform' — positioning is integration, not underwriting.
Curated set excludes carriers Awning's own editorial recommends
The marketplace omits Steadily, Safely, CBIZ, and Farmers, even though Awning's STR roundup highlights CBIZ as specializing in rental property insurance and Farmers for first-claim forgiveness — creating editorial-vs-marketplace inconsistency.
AM Best and underwriter details not on the marketplace page
Awning's per-reservation product page only says it 'can connect hosts with multiple different insurance companies depending on the property' without naming an underwriter, forcing buyers to click through to each partner site to verify carrier financial strength.
First-party pricing URL is missing
The dedicated /str-insurance/pricing path returned 404 on 2026-04-26, so all pricing has to be extracted from marketing copy on the marketplace landing page rather than a canonical pricing URL.
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 Awning Insurance if
First-time Airbnb investors who want one comparison page for Proper, Obie, Toggle, and Hippo without filling out four separate quote forms.
Skip Awning Insurance if
You run commercial-zoned units, international properties, or non-standard occupancy — Awning's curated set is U.S.-only and skewed toward residential single-family Airbnb use.
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
Awning Insurance
Useful triage page for new Airbnb investors; thin if you already know the STR carrier landscape
InsuraGuest
Affordable flat-rate guest protection layer for PMS-connected operators