What Proper Insurance does

Proper Insurance Services, LLC operates as a specialty Managing General Agent (MGA) and Coverholder at Lloyd's of London, underwriting and distributing commercial homeowners insurance purpose-built for short-term rental (STR) properties. Founded in 2014 and headquartered in Bozeman, Montana with a satellite office in Frederick, Maryland, the company is licensed across all 50 U.S. states and Washington D.C., with policies backed by Lloyd's of London and Concert Specialty Insurance Company. The company's underwriting architecture replaces standard homeowners and landlord policies with a unified Commercial Homeowners form covering building, contents, commercial general liability up to $1M, and business revenue protection with no time limit, augmented by trade-dressed endorsements for STR-specific risks (Property Entrustment, Squatters Protection, Bed Bug & Flea Protection, Pet & Animal Liability, Liquor Liability, Amenities On & Off-Premises, and Property Manager Commission Income Protection).

The business operates on subscription-based, quote-driven insurance premiums paid annually by property owners and managers, with revenue mechanics typical of an MGA: collecting gross written premium and retaining commission/fees while ceding risk to Lloyd's and Concert Specialty. Distribution is direct-to-consumer via a self-serve quoting portal (portal.proper.insure), a dedicated phone line (888-631-6680), and a nationwide licensed agent/broker program, augmented by an exclusive endorsement from Vrbo that drives referrals from one of the largest U.S. vacation rental platforms. Customer segments are individual STR property owners (Airbnb, Vrbo, Booking.com hosts), professional property managers handling multi-property portfolios, and rental arbitrage operators who lease and re-list properties.

Proper has written over 200,000 policies cumulatively across the U.S. and operates as a subsidiary of Specialty Program Group (SPG) following its February 2026 acquisition. The company has 101-250 employees and is led by President Michael Grimland (appointed post-acquisition; Director of Operations since 2017), with a leadership team including a Chief Sales Officer and Chief Marketing Officer specialized in the STR vertical. The product moat rests on being the only commercial homeowners policy designed end-to-end for short-term rentals, distributed through a regulated 50-state licensing footprint and anchored by Lloyd's underwriting capacity.

Name

Proper Insurance

Legal name

Proper Insurance Services, LLC

Website

https://proper.insure

Company type

Private

Founded year

2014

Operating status

Acquired

Headcount range

101–250 employees

Short description

Proper Insurance is a U.S. specialty MGA and Lloyd's of London Coverholder underwriting commercial homeowners insurance purpose-built for short-term rental properties, serving individual hosts, property managers, and rental arbitrage operators across all 50 states.

Ownership category

akta.pro rank

Product category

Specialty Short-Term Rental Insurance

NAICS

Direct Property and Casualty Insurance Carriers (524126), Direct Insurance (except Life, Health, and Medical) Carriers (52412), Other Direct Insurance (except Life, Health, and Medical) Carriers (524128)

SIC

Fire, Marine & Casualty Insurance (6331), Insurance Carriers, Nec (6399)

akta.pro primary industry

Homeowners Insurance (FSAJACAA)

akta.pro secondary industry

Public Liability (Premises/Operations) (FSAJADAD)

Keywords

• Short-term rental insurance
• Vacation rental insurance
• Airbnb host insurance
• Vrbo host insurance
• Rental arbitrage insurance

Headquarters

HQ city

Frederick

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Operations, Personnel, Marketing or Sales, Technology or R&D, Others

Revenue model

1. Specialty Short-Term Rental Insurance Premiums: Proper Insurance generates revenue through insurance premium payments from policyholders. Property owners and managers pay recurring premiums for specialized commercial homeowners insurance coverage tailored to short-term rental operations. Pricing is subscription-based and quote-driven, with no public rate cards.

Pricing tiers

Go-to-market motion1 record

Distribution channels4 records

Marketing channels7 records

Core offering

Proper Insurance offers specialized Commercial Homeowners insurance designed exclusively for short-term rental properties, replacing standard Homeowners and Landlord policies. The core policy covers building, contents, commercial general liability up to $1M, and lost business revenue, and is supplemented by trade-dressed endorsements such as Property Entrustment (guest damage), Squatters Protection, Bed Bug & Flea Protection, Pet & Animal Liability, Liquor Liability, and Amenities On & Off-Premises coverage. Coverage is underwritten by Lloyd's of London and Concert Specialty Insurance Company, and is available in all 50 US states and Washington D.C.

Product overview

Proper Insurance offers a unified Commercial Homeowners insurance policy purpose-built for short-term rental properties. The core Short-Term Rental Insurance product replaces standard Homeowners or Landlord policies entirely, with building/contents coverage, Commercial General Liability, and Business Revenue Protection as foundational components. The portfolio spans dedicated coverage lines for Airbnb hosts, Vrbo owners, vacation rentals, and rental arbitrageurs, all underwritten by Lloyd's of London and Concert Specialty. Specialized add-on coverages include Property Entrustment, Pet & Animal Liability, Bed Bug & Flea Protection, Squatters Protection, Amenities On & Off-Premises, and Liquor Liability. The company also offers a Property Manager Commission Income Protection endorsement, making it the only comprehensive STR insurance policy in the U.S. market.

Differentiator

Problem solved

Functional benefit

Products and services

• Short-Term Rental Insurance The primary Commercial Homeowners policy designed to replace standard Homeowners or Landlord insurance for short-term rental properties. Covers building, contents, commercial general liability up to $1M, and lost business revenue with no time limit. Positioned for short-term rental owners, vacation rental owners, Airbnb hosts, Vrbo owners, and rental arbitrage operators.
• Property Entrustment Trade-dressed insurance coverage protecting short-term rental property owners against theft, vandalism, and intentional or malicious damage caused by guests. Excluded from standard Homeowners and Landlord policies.
• Squatters Protection First-of-its-kind squatters protection providing up to $20,000 in loss of business revenue and up to $10,000 in actual expenses (eviction costs, court costs, sheriff fees) when a guest refuses to leave the property.
• Bed Bug & Flea Protection First-to-market coverage for liability, extermination costs, and lost revenue from canceled bookings due to bed bug or flea infestations in short-term rental properties.
• Pet & Animal Liability Coverage for pet and animal liability with no breed restrictions or animal exclusions. Protects hosts from liability for dog bites and other animal-related incidents, whether guests bring pets or not.
• Liquor Liability Coverage for hosts offering or providing alcohol on the premises, including wine in welcome baskets or left-behind liquor that may be consumed by subsequent guests.
• Amenities On & Off-Premises Coverage Coverage for liability arising from amenities that take guests off-premises (e.g., bikes, kayaks, golf carts) and common amenities such as pools and hot tubs.
• Commercial Business Liability Commercial General Liability protection starting at $1M, extending beyond the premise and following guests, covering incidents on and off-premises including pet/animal, liquor liability, and invasion of privacy.
• Property Manager Commission Income Protection First-of-its-kind endorsement built into every policy, providing property managers a business income check alongside the owner under a business income claim during a covered loss event.

Quantifiable outcome

• Over 200,000 policies written across all 50 states and Washington D.C.

Segments5 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature4 records

Partnerships

17 partnerships are on record, tiered core and minor.

• VrbocoreChannel Partner/ Reseller/ DistributorProper Insurance is exclusively endorsed by Vrbo as their preferred insurance provider. This endorsement is a primary customer acquisition channel, giving Proper Insurance preferential referral access to Vrbo's host base. The endorsement serves as a third-party validation of Proper Insurance's product-market fit for the short-term rental market.
• WaivominorGTM or Marketing PartnerWaivo is listed as a Vacation Rental Damage Protection partner, offering integrated damage protection solutions for short-term rental operators alongside Proper Insurance.
• WisterminorGTM or Marketing PartnerWister is a hospitality insurance agency partner that works with short-term rental operators, potentially referring customers to or from Proper Insurance.
• Host FinancialminorGTM or Marketing PartnerHost Financial specializes in STR (short-term rental) loans and financing, providing specialized financing solutions for short-term rental property investors who may be Proper Insurance customers.
• NectarminorGTM or Marketing PartnerNectar offers cash flow-based financing for short-term rental operators, serving the same customer base as Proper Insurance.
• NovominorGTM or Marketing PartnerNovo provides small business banking services, targeting small business owners and operators who may also purchase Proper Insurance coverage.
• StayFiminorGTM or Marketing PartnerStayFi provides WiFi and guest marketing solutions for short-term rental properties, serving the same customer base as Proper Insurance.
• TurnominorGTM or Marketing PartnerTurno helps short-term rental hosts find vetted cleaners, serving the same Airbnb and vacation rental host customer base as Proper Insurance.
• ASTRHOminorGTM or Marketing PartnerThe Association for Short-Term Rental Homeowners (ASTRHO) is an industry association that advocates for and supports short-term rental property owners, serving the same customer base as Proper Insurance.
• Host2HostminorGTM or Marketing PartnerHost2Host is an Oregon-based host association supporting short-term rental operators in the Pacific Northwest, serving a regional subset of Proper Insurance's customer base.
• Rent ResponsiblyminorGTM or Marketing PartnerRent Responsibly is a short-term rental advocacy group that educates and advocates for responsible STR hosting, serving the same customer base as Proper Insurance.
• The Distinguished GuestminorGTM or Marketing PartnerThe Distinguished Guest is an industry educator providing training and education for short-term rental hosts and property managers, serving the same customer base as Proper Insurance.
• Rental ReconminorGTM or Marketing PartnerRental Recon provides Airbnb information and advice for short-term rental operators, serving the same customer base as Proper Insurance.
• Thanks For VisitingminorGTM or Marketing PartnerThanks For Visiting is an industry educator providing content and resources for short-term rental hosts, serving the same customer base as Proper Insurance.
• TripzminorChannel Partner/ Reseller/ DistributorTripz is a booking platform for short-term rentals, serving property owners and operators who may also purchase Proper Insurance coverage.
• Red AwningminorChannel Partner/ Reseller/ DistributorRed Awning provides marketing and management services for short-term rental properties, serving property owners who may also be Proper Insurance customers.
• California Design DenminorGTM or Marketing PartnerCalifornia Design Den provides bedding and linens for short-term rental properties, serving the same short-term rental operator customer base as Proper Insurance.

Scale indicators2 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Safely: Safely is a direct competitor offering vacation rental-specific damage protection and insurance products for short-term rental hosts on platforms like Airbnb and Vrbo, overlapping with Proper's Property Entrustment and core STR coverage.
• Superhog: Superhog provides guest screening combined with damage protection and insurance products for the vacation rental industry, directly competing with Proper for STR host coverage and risk management.
• RentalGuardian: RentalGuardian offers vacation rental damage protection and liability insurance plans marketed to property managers and individual hosts, competing in the same STR insurance niche as Proper.

Emerging players

• AssureStays: AssureStays is a niche insurance provider focused on short-term and vacation rental properties, offering specialized liability and property coverage that overlaps with Proper's core product set.
• Slice Labs: Slice is a digital insurance platform that enables on-demand, embedded insurance products via API, sharing Proper's specialty insurance distribution model though serving broader lines beyond STR.
• Cover Genius: Cover Genius is an embedded insurance provider offering tailored coverage for the sharing and rental economy, including short-term rentals, with technology-driven distribution similar to Proper's online quoting portal.
• Hippo Insurance: Hippo is a digital-first homeowners insurance carrier that has expanded into adjacent property coverages; while broader than Proper, it competes for modern homeowners insurance customers who also operate rentals.

Broad incumbents

• Lemonade: Lemonade is a major digital insurance carrier offering homeowners and renters policies with an AI-driven, direct-to-consumer model. It is a broader incumbent in the digital property insurance space that could expand into STR coverage.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights6 records

Customer concentration

• Xx.com/ProperIns

Revenue estimate

Valuation estimate

Number of profiles

Profiles6 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Proper Insurance