The best STR insurance providers for operators and investors in 2026

Proper Insurance — Best overall STR-specific coverage

Best for: most STR operators who want comprehensive purpose-built coverage

Starting price: ~$1,500-$3,500/yr

Proper Insurance is the most widely recommended STR-specific insurance policy in the professional vacation rental industry. It is built exclusively for short-term and vacation rentals — not adapted from a landlord policy or homeowner rider. Coverage includes commercial liability up to $1M per occurrence, loss of rental income, guest property damage, and building/contents protection. The policy is backed by Lloyd's of London, which provides materially stronger financial backing than many newer InsurTech competitors. Claims process is STR-aware, meaning adjusters understand vacation rental operations.

Skip if: your investor client needs fast online quote-to-bind for a DSCR loan closing — Steadily's faster underwriting process may be more practical under time pressure.

What to tell your client: "This is what professional vacation rental managers carry. AirCover is a guest-facing marketing program, not a commercial insurance policy. You need a real policy."

Steadily — Best for DSCR investor clients needing fast quotes

Best for: real estate investors who need quick quote-to-bind for financing or portfolio coverage

Starting price: Varies — online quote available

Steadily offers the fastest online quote-to-bind experience in the STR insurance market, which makes it particularly well-suited for investor clients who need proof of insurance quickly for a DSCR loan closing or a new acquisition. Policies include $1M+ liability options, dwelling coverage, and rental income protection. Steadily has built a reputation in the real estate investor community and integrates with property management workflows. The tradeoff vs. Proper is that Steadily is a broader landlord/rental product whereas Proper is exclusive to STR.

Skip if: your client has time to shop and wants the most comprehensive STR-specific policy — Proper Insurance is the stronger product for established operators.

What to tell your client: "If you need insurance bound quickly for a closing, Steadily can move fast. For long-term coverage on an established property, we'd compare Proper Insurance."

CBIZ — Best for large portfolio commercial lines

Best for: professional management companies or investors with 10+ STR properties

Starting price: Custom commercial lines pricing

CBIZ is a commercial insurance brokerage that provides blanket commercial lines policies for vacation rental management companies and portfolio investors. At scale, individual-property STR policies become expensive and administratively complex — CBIZ's commercial approach covers the portfolio under a single commercial policy with aggregate limits. Best for professional managers running 10+ properties who need a sophisticated insurance program rather than per-property consumer products.

Skip if: you're an individual operator with 1-5 properties — the commercial lines overhead doesn't make sense at this scale.

Slice — Best pay-per-night on-demand coverage

Best for: occasional STR operators or operators supplementing existing homeowner coverage

Starting price: ~$4-10/night

Slice offers on-demand STR coverage that activates per booking or per night — operators pay only when the property is actively rented to guests. This model works well for homeowners who rent occasionally (10-50 nights per year) and want guest-specific coverage without annual STR policy premiums. For high-occupancy professional operators, the per-night economics quickly exceed an annual policy. Slice coverage includes liability and property damage per booking.

Skip if: your property runs 60%+ occupancy — the annual math heavily favors a standard STR policy like Proper or Steadily.

Hippo — Best for bundled home + STR coverage

Best for: owner-occupied properties with STR activity who want a single carrier

Starting price: Varies by property and coverage

Hippo is a home insurance carrier that offers bundled coverage for properties that are primarily owner-occupied but also used for short-term rental. The bundled approach simplifies insurance administration for owner-occupants who don't want separate policies. Coverage includes smart home protections, extended replacement cost, and can be structured to accommodate rental activity. Hippo is strongest for the owner-occupant who rents occasionally, not the full-time dedicated STR operator.

Skip if: the property is a dedicated investment STR, not your primary or secondary residence — Proper Insurance is the right product for dedicated rental properties.