Obie Insurance Review: Landlord & Rental Property Coverage Explained

Finding the right landlord insurance can be confusing—even for seasoned real estate investors. Underinsuring your rental property leaves you vulnerable to unexpected losses, while overpaying cuts directly into your cash flow and reduces returns. That’s why investors are turning to modern, data-driven platforms like Obie Insurance for faster quotes, transparent coverage, and investor-friendly pricing.

Obie Insurance is a tech-driven insurtech company that simplifies coverage for landlords and rental property owners. Instead of dealing with traditional brokers and paperwork, investors can compare, customize, and purchase landlord policies entirely online. This Obie Insurance Review breaks down everything you need to know so you can decide whether it’s the right solution for protecting your portfolio.

In 2025, Obie continues to expand coverage across more states and roll out enhanced integrations with property management and lending platforms—making it easier than ever for real estate investors to secure and manage insurance digitally. As policies, pricing, and state availability evolve, staying up to date on what Obie offers is essential for making smart insurance decisions that protect your investments and maximize your ROI.

In this comprehensive review, you’ll learn:

• What Is Obie Insurance?
• Coverage Options
• Pricing & Rates
• Pros & Cons
• Competitors
• Legitimacy & Safety
• Who Should Use Obie Insurance?
• Final Verdict & Alternatives
• FAQ

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What Is Obie Insurance & Who Created It?

Obie Insurance is a next-generation insurtech platform designed specifically for landlords and real estate investing. Rather than relying on outdated agents and manual paperwork, Obie delivers a fully digital experience—allowing property owners to quote, customize, and purchase insurance online in just minutes. The goal is simple: make rental property insurance transparent, affordable, and easy to manage.

Founded by Ryan Letzeiser and Joe Kruer, Obie was born out of frustration with the slow, fragmented insurance process that real estate investors often face. Both co-founders came from real estate and technology backgrounds and understood how difficult it was for landlords to find coverage that truly fit their needs. They built Obie to bridge that gap, combining the precision of data-driven underwriting with the convenience of modern technology. Headquartered in Chicago, Illinois, Obie has grown into one of the most recognized insurtech names in the investor space.

Today, Obie offers coverage in most U.S. states, including key real estate markets like California, Florida, Texas, Georgia, and Illinois, with plans to expand nationwide. The platform has been used to insure over $10 billion in property value and continues to attract attention from institutional investors and independent landlords alike. 

For real estate investors, Obie represents a fundamental shift in how insurance is handled. Instead of waiting days for quotes or juggling separate policies for each property, landlords can now bundle multiple properties, compare coverage options instantly, and secure policies that align with their investment goals. Whether you own one rental or a hundred, Obie’s data-driven platform makes coverage more efficient, cost-effective, and scalable.

Key Features Investors Love About Obie

• Instant Quotes: Get landlord insurance estimates in under five minutes—no agent phone calls or paperwork.
• Portfolio Coverage: Manage insurance for multiple properties under one digital dashboard.
• Tailored Policies: Coverage designed specifically for rental properties, not generic homeowner plans.
• Competitive Pricing: Obie partners with top-rated carriers to find investor-friendly rates.
• Integrated Technology: Connects seamlessly with property management tools like AppFolio and Buildium.

Ultimately, Obie Insurance gives landlords more control, better pricing, and peace of mind. However, insurance is just one part of building a successful real estate business; understanding how to find, fund, and manage investments effectively is what truly drives long-term growth.

Build a Smarter Investment Foundation

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Obie Insurance Coverage Options & Features

Obie Insurance offers flexible coverage options designed for rental property owners and real estate investors. Instead of cookie-cutter homeowner policies, Obie structures protection around the specific risks landlords face—covering the building, rental income, liability, and more. Every policy can be customized to fit a single-family rental, multi-unit property, or full real estate portfolio.

Categories of Coverage

Obie’s core insurance options mirror what experienced investors expect from a dedicated landlord policy, with the ability to expand or fine-tune coverage depending on the property type:

• Dwelling/Property Coverage: Protects the building’s physical structure from events such as fire, wind, hail, and vandalism.
• Liability Protection: Covers legal costs and settlements if a tenant, visitor, or contractor is injured on the property.
• Personal Property: Covers items owned by the landlord (e.g., appliances or furnishings in furnished rentals).
• Loss of Rent: Covers your lost rental income when a covered event — such as fire, storm damage, or another insured peril — makes the property temporarily uninhabitable.
• Optional Endorsements: Add-ons such as water backup, vandalism, equipment breakdown, and special hazard protection can be included for enhanced peace of mind.

Special Programs for Investors

Obie also caters to diverse investor needs through specialized programs built around modern rental models:

• Portfolio Policies: Bundle multiple properties—across states or entity structures—under one streamlined policy for simplicity and savings.
• Short-Term Rental Coverage: Protects Airbnb, VRBO, and vacation rentals with specific endorsements for higher guest turnover risk.
• Umbrella Liability: Expands protection limits beyond the base policy for high-net-worth landlords or investors managing large portfolios.

Claims Process & Customer Experience

Obie’s fully digital platform allows landlords to get a quote, manage policies, and file claims online—often in minutes. The interface is simple and intuitive, allowing investors to view multiple properties, update coverage, and add endorsements without phone calls or paperwork. Each account includes access to a dedicated team member or licensed representative for questions or claim assistance. Many users report quote turnaround times under 5 minutes and consistently rate Obie’s ease of use among the best in the landlord insurance industry.

Feature Comparison Table

 

Coverage Type	What It Covers
Dwelling Protection	Covers the building’s structure against fire, wind, hail, theft, and other covered events.
Liability Coverage	Protects against lawsuits or injury claims from tenants or visitors on the property.
Personal Property	Insures the landlord’s owned items, like appliances, furniture, or maintenance tools.
Loss of Rent	Reimburses lost rental income when the unit becomes uninhabitable due to a covered peril.
Optional Endorsements	Add-ons like water backup, vandalism, or equipment breakdown coverage.

 

 

Obie Insurance Pricing & Rating Factors

Obie Insurance provides straightforward, investor-focused pricing built specifically for landlords and rental property owners. Instead of relying on time-consuming phone calls or manual quotes, Obie’s digital platform uses real property details to generate accurate premiums within minutes. The result is a faster, more transparent experience that often leads to lower rates and smoother underwriting—without surprise fees or long waiting periods.

How Obie Pricing Works

Your Obie insurance premium depends on several key variables:

• Property Location: Rates vary by state, zip code, and exposure to natural disasters (e.g., hurricanes, floods, wildfires).
• Property Type: Single-family homes, multi-family units, and short-term rentals carry different risk profiles.
• Coverage Limits: Higher coverage equals higher premiums, especially for larger portfolios or high-value properties.
• Deductible: Choosing a higher deductible generally reduces annual premiums.
• Claims History: Fewer prior claims often result in better rates.
• Credit Profile & Entity Type: Obie considers your investor or business profile to assess pricing accuracy and discounts.

Typical Cost Ranges

While pricing depends on individual property factors, Obie’s rates tend to be below traditional market averages. Here are general ranges to help investors estimate their annual cost:

 

Property Type	Coverage Level	Typical Annual Premium
Single-Family Rental	Basic coverage (dwelling + liability)	$500 – $1,000
Multi-Family Property (2–4 units)	Standard coverage + loss of rent	$1,200 – $1,800+
Short-Term or Vacation Rental	Enhanced liability & guest coverage	$1,000 – $2,000+
Portfolio Policy (5+ properties)	Custom coverage across multiple states	$4,000 – $10,000+ (depends on volume & limits)

 

Discounts & Savings Opportunities

Obie offers flexible ways to save while maintaining full coverage:

• 💡 Security Discounts: Lower rates for properties with alarms, cameras, and smart locks.
• 🏠 Multi-Property Discounts: Save by insuring multiple rentals under one portfolio policy.
• 📦 Bundled Coverage: Combine dwelling and liability for streamlined protection at better pricing.
• ⚡ No Agent Commissions: Obie’s digital process removes middlemen, cutting administrative costs.

 

Pros & Cons of Obie Insurance

Like any insurance platform, Obie Insurance comes with its strengths and trade-offs. Real estate investors appreciate its tech-forward convenience, competitive pricing, and investor-focused coverage options, but some may prefer traditional brokers for complex or high-risk portfolios. Here’s how the advantages and disadvantages stack up:

 

Pros	Cons
Tailored insurance for real estate investors — no generic homeowner policies.	Limited availability in certain states; not yet nationwide.
Fast, digital quoting and policy binding process that takes minutes instead of days.	Digital-first model — some investors prefer local agents or in-person service.
Competitive premiums with robust coverage flexibility and add-ons.	Premiums may rise for older or high-risk properties.
Portfolio-friendly policies for landlords managing multiple rentals.	Relatively new company with a shorter track record compared to legacy insurers.

 

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Obie Insurance vs Competitors

When choosing landlord insurance, real estate investors often compare Obie Insurance to other major providers like Steadily, State Farm, Farmers, Travelers, and newer insurtechs such as Lemonade and SFR Insurance. Each platform brings different strengths — from nationwide coverage to unique investor tools — but Obie sets itself apart by focusing exclusively on landlords and property investors rather than traditional homeowners.

Here’s how Obie stacks up against its competitors in terms of coverage, service, and pricing:

 

Platform	Core Strengths	Weaknesses	Typical Pricing Range	Best For
Obie Insurance	Investor-focused platform with instant digital quotes, portfolio coverage, and landlord-specific policies.	Limited availability in some states; newer company with shorter track record.	≈ $500 – $1,500 / year per property (varies by type & location)	Landlords & real estate investors seeking speed and tailored coverage.
Steadily	Strong digital quoting platform with broad landlord coverage across all 50 states.	May be slightly higher priced for multi-property portfolios.	≈ $600 – $1,800 / year	Individual landlords and small-scale investors wanting quick online service.
State Farm	Established nationwide provider with strong claims support and agent network.	Slower quoting process; policies not designed for active investors.	≈ $700 – $2,000 / year	Traditional landlords preferring in-person agents.
Farmers / Travelers	Comprehensive property insurance options with high liability limits.	Lengthy underwriting; slower claims compared to digital competitors.	≈ $800 – $2,500 / year	Owners of higher-value properties seeking maximum coverage.
Lemonade	AI-driven claims process and transparent pricing; quick mobile app.	Limited rental property coverage; designed mainly for tenants or homeowners.	≈ $400 – $1,000 / year	Short-term rental owners or small landlords seeking low-cost coverage.

 

Key takeaway: While Steadily and Lemonade lead in speed and digital accessibility, and State Farm and Travelers offer legacy reliability, Obie’s niche lies in serving real estate investors — especially those managing multiple units or portfolios who value data-driven underwriting and fast policy binding.

 

Legitimacy & Safety: Is Obie Insurance Legit?

Before purchasing any landlord insurance policy, it’s natural to ask whether the provider is legitimate and trustworthy. The good news is that Obie Insurance operates as a fully licensed insurance agency across most U.S. states, working with financially strong, AM Best-rated carriers to underwrite its policies. This structure ensures that your coverage is backed by reputable insurers—not an unregulated tech startup.

Licensing & Regulation

Obie is licensed as an insurance producer and broker, compliant with state-specific regulations. The company partners with well-established carriers that meet or exceed AM Best’s “A-” financial strength rating, meaning those insurers have the capital to pay claims reliably. Investors can confirm Obie’s licensing through their state’s Department of Insurance or the NAIC license lookup tool.

Trustworthiness & Reviews

Online feedback about Obie Insurance is generally positive, especially among landlords and property investors who appreciate the streamlined quote process and responsive support. Trustpilot and Google reviews mention quick claim responses and fair pricing, though some note limited local agent access and occasional underwriting delays for complex portfolios. 

Website & Data Security

Obie’s website uses SSL encryption to protect personal and financial data. The platform complies with standard data-privacy protocols and state insurance regulations. However, investors should still verify individual carrier credentials and review policy documents before binding coverage—an essential step in any digital insurance transaction.

 

Who Should Use Obie Insurance?

Obie Insurance is designed specifically for real estate investors—those managing rental properties, scaling portfolios, or using strategies like BRRRR and value-add renovations. Unlike traditional homeowner’s insurance, Obie tailors its coverage to landlords and investor needs, offering flexible protection for single-family, multi-family, and mixed-use rentals. If you want digital management, portfolio pricing, and quick binding, Obie may be a perfect fit.

Ideal Users

• Active real estate investors with multiple rentals or high-value portfolios looking for centralized management.
• BRRRR investors and developers who need temporary or renovation coverage that adapts as projects progress.
• Landlords seeking instant digital quotes, easy renewals, and paperless policy updates.
• Real estate professionals and institutional investors who prioritize automation, data-driven pricing, and portfolio-level efficiency.

Not Ideal For

• Small landlords with low-value properties under roughly $100,000, where portfolio or insurtech features add unnecessary cost.
• Owner-occupants or homeowners seeking personal residence coverage—Obie focuses solely on rental and investment property.
• Investors in states with limited Obie availability (always verify coverage area before applying).

 

Criteria	Good Fit	Poor Fit
Property Value	$100K–$5M+ (single- or multi-family)	Under $100K
Investment Strategy	Buy-and-hold, BRRRR, or value-add investing	Owner-occupied or primary residence
Preferred Experience	Fast digital quotes, portfolio management, online claims	In-person agent relationships
Coverage Area	States where Obie operates (verify on website)	States without active licensing

 

 

Final Verdict & Alternatives

After reviewing Obie Insurance from every angle, it’s clear that the platform stands out as one of the best landlord insurance solutions for real estate investors. Its investor-first approach, competitive pricing, and fast digital quoting make it especially appealing for those managing rental portfolios or using scalable strategies like BRRRR and buy-and-hold investing. For property owners seeking a frictionless way to get insured, Obie delivers convenience without compromising coverage quality.

That said, there are some trade-offs. Availability may vary by state, and the platform’s digital-first model might not appeal to landlords who prefer local, face-to-face support. However, for most investors—especially those comfortable managing their business online—Obie strikes a strong balance between speed, customization, and cost savings.

Our Recommendation

We recommend that investors get a quote from Obie and compare it with a few alternatives to ensure you’re getting the best rate and coverage for your property type. Even small premium differences can translate into thousands of dollars saved across multiple properties, so it pays to shop around while taking advantage of Obie’s easy, digital quoting system.

Top Alternatives to Consider

• Steadily – Another investor-focused insurer known for wide state coverage and simple digital quotes.
• State Farm – Traditional carrier offering personal service, strong claims history, and local agent relationships.
• Lemonade – Fully digital insurer with AI-driven claims and transparent pricing, better suited for smaller portfolios.
• Farmers & Travelers – Established national carriers offering flexible property and liability options for diverse rental portfolios.

Frequently Asked Questions (FAQ)

Here are answers to the most common questions investors ask about Obie Insurance. These quick insights cover everything from coverage and pricing to claims and availability, helping landlords decide whether Obie is the right fit for their rental portfolio.

What is Obie Insurance?

Obie is a digital insurance platform that provides landlord and rental property insurance for investors, offering coverage for single-family, multi-family, and short-term rental properties.

How do I get a quote from Obie?

You can get a free quote directly on Obie’s website in minutes by entering basic property details—no lengthy phone calls or paperwork required.

What types of property does Obie cover?

Obie covers single-family rentals, multi-family units, apartment buildings, condos, and short-term rentals like Airbnb or VRBO properties.

Is Obie available in all states?

Obie is licensed in most U.S. states, but availability can vary. Check their website or contact support to confirm if your property’s location is eligible.

How does Obie’s pricing compare to other insurers?

Many landlords find Obie’s premiums to be 10–20% lower than traditional carriers, thanks to its digital underwriting and investor-specific risk models.

Can I bundle multiple properties in one policy?

Yes. Obie allows investors to bundle portfolios under one policy, simplifying management and potentially reducing total premiums.

Does Obie cover short-term rentals?

Yes, Obie offers coverage options tailored for short-term and vacation rental properties, protecting against unique risks like guest damage or loss of income.

How is Obie rated by customers?

Customer reviews generally highlight fast quotes, competitive pricing, and excellent digital support. Some investors note that in-person agent access is limited due to the platform’s digital-first model.

What happens if I need to file a claim with Obie?

Claims can be filed online or through a dedicated support representative. Obie’s partner carriers process claims directly, with most responses initiated within a few business days.

Is Obie suitable for high-net-worth investors?

Yes. Obie provides scalable coverage solutions for large portfolios and high-value rental properties, making it suitable for both independent landlords and institutional investors.

Conclusion & Next Steps

According to our Obie Insurance review, this company has quickly established itself as one of the most innovative insurtech platforms for real estate investors and landlords. By simplifying the quoting process, providing transparent policy options, and offering competitive premiums tailored to rental properties, Obie helps investors protect their assets while keeping cash flow strong.

That said, Obie isn’t the perfect fit for everyone. Coverage availability varies by state, and investors who prefer face-to-face service or long-standing carriers may lean toward more traditional options. Still, for tech-savvy landlords who value speed, convenience, and investor-focused coverage, Obie delivers a clear advantage.

As with any major investment decision, the best strategy is to compare quotes from several reputable providers—including Obie—to ensure your rental portfolio receives the protection it deserves at the most competitive rate.

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*Disclosure: Real Estate Skills is not a law firm, and the information contained here does not constitute legal advice. You should consult with an attorney before making any legal conclusions. The information presented here is educational in nature. All investments involve risks, and the past performance of an investment, industry, sector, and/or market does not guarantee future returns or results. Investors are responsible for any investment decision they make. Such decisions should be based on an evaluation of their financial situation, investment objectives, risk tolerance, and liquidity needs.