Tired Landlord Guide: Selling Your Florida Rental Property (Even with Tenants)

Florida is the number one state in the country for rental property investment. With over 1.4 million single-family rental units, a booming population, and a landlord-friendly legal framework, the Sunshine State has attracted investors from every corner of the nation.

But owning rental property in Florida in 2026 is not what it was five years ago. Insurance premiums have skyrocketed. Property taxes have climbed alongside rising assessments. Tenants expect more. And the late-night phone calls about a broken AC unit in July humidity never seem to stop.

If you are reading this, you are probably what the industry calls a "tired landlord." That is not a criticism. It is a recognition that the investment thesis has changed, the math may no longer work, and you are ready to explore your options. This guide walks you through exactly how to sell your Florida rental property, what the law requires, and how to maximize your return when you do.

Signs You're a Tired Landlord

Landlord fatigue does not happen overnight. It builds gradually, one maintenance call and one insurance renewal at a time. Here are the warning signs that it may be time to sell.

You Dread Tenant Calls

When your phone rings and it is your tenant, your first reaction is dread rather than routine. Every call feels like another problem to solve, another expense to absorb, another argument about what qualifies as normal wear and tear versus damage. This emotional shift is significant. When managing your investment feels like a burden rather than a business activity, the psychological cost is real.

Repairs Are Eating Into Profits

Florida's climate is brutal on buildings. Salt air corrodes metal, humidity breeds mold, hurricane seasons demand preparation, and the relentless sun degrades roofing, paint, and sealant faster than in temperate climates. What used to be a $500-per-year maintenance budget has become $3,000 to $5,000 or more. Aging HVAC systems in Florida do not last as long as they do in northern states, and a replacement unit can run $8,000 to $15,000. When your annual maintenance costs start approaching or exceeding a month's rent, the numbers stop working.

Insurance Costs Have Made the Investment Negative

This is the big one for Florida landlords. Landlord insurance premiums in Florida have increased 40-100% since 2022, and some carriers have exited the state entirely. If you were cash flowing $300 per month on a rental and your annual insurance premium jumped from $2,400 to $5,500, you just lost $258 per month in profit. Many Florida landlords who were positive cash flow in 2021 are now break-even or negative after insurance increases alone.

Property Management Fees and Vacancy Are Eroding Returns

Professional property management in Florida typically runs 8-10% of monthly rent, plus leasing fees equal to one month's rent for each tenant placement. Add a month of vacancy between tenants, turnover costs for cleaning, painting, and minor repairs, and the effective management cost can reach 15-20% of gross rent. For a property renting at $2,000 per month, that is $3,600 to $4,800 per year in management costs alone, before factoring in any vacancy.

Emotional Burnout

Perhaps the most overlooked factor. You bought the property as an investment, but it has become a source of stress. You lie awake wondering if the roof will survive the next hurricane season. You check your bank account after rent is due, hoping the payment went through. You spend weekends driving to the property instead of spending time with family. Investment real estate should improve your quality of life, not diminish it.

Florida Landlord-Tenant Law Basics for Sellers

Before you list your property or accept an offer, you need to understand your legal obligations. Florida Statute Chapter 83, the Residential Landlord and Tenant Act, governs the relationship between landlords and tenants, and its requirements do not disappear just because you are selling.

Leases Transfer with the Property

This is the most important thing to understand: when you sell a rental property in Florida, the existing lease transfers to the new owner. The new buyer inherits all the terms, conditions, and obligations of the current lease. You cannot simply terminate a lease because you are selling the property.

• Fixed-term leases: If your tenant has a lease that runs through December 2026, the new owner must honor that lease through December 2026. The rent amount, terms, and conditions remain the same.
• Month-to-month tenancies: The new owner can issue a 15-day written notice to terminate a month-to-month tenancy. The notice must be delivered at least 15 days before the end of the monthly period.

Security Deposit Obligations

Under Florida law, security deposit obligations transfer to the buyer at closing. You must either return the deposit to the tenant or transfer it to the new owner. This should be handled explicitly in your purchase agreement. Most closings account for security deposits as a credit to the buyer, but you should verify with your closing agent that this is properly documented.

Notice Requirements for Showing the Property

Florida law requires reasonable notice before entering a tenant's unit. While the statute does not specify an exact number of hours, courts have generally interpreted "reasonable" as at least 12 hours advance notice. During the sales process, you may need to show the property to prospective buyers, inspectors, and appraisers. Establish clear communication with your tenants early. Let them know the property is being sold, explain their rights, and agree on a showing schedule that works for everyone.

Orange County Tenant Bill of Rights Considerations

If your rental property is in Orange County (Orlando metro area), be aware of additional local protections. The Orange County Tenant Bill of Rights, enacted in 2023, requires landlords to provide 60-day notice of rent increases exceeding 5% and establishes additional disclosure requirements. While this ordinance primarily affects lease renewals, it reflects a trend of local jurisdictions adding tenant protections beyond what state law requires. Check your specific county and municipal regulations before proceeding.

Your Options for Selling a Rental Property

You have four primary paths to sell your Florida rental. Each has trade-offs in terms of price, speed, and complexity.

Option 1: Wait for the Lease to Expire, Then Sell Vacant

This is the most conventional approach. You let the current lease run out, do not renew, and list the property once the tenant has vacated.

Pros:

• Cleaner sale process with no tenant complications
• Broader buyer pool including owner-occupants and investors
• Easier to show, stage, and photograph the property
• No lease assignment complications at closing

Cons:

• Lost rental income during the vacancy period (listing, showing, closing)
• Property can deteriorate quickly when empty, especially in Florida's climate
• Ongoing insurance, taxes, and maintenance costs with no income to offset them
• Risk of vandalism or code violations on vacant property
• May need to wait months for the current lease to expire

Option 2: Sell with Tenant in Place to a Traditional Buyer

You list the property on the MLS while the tenant remains. Some buyers, particularly investors, will purchase a tenant-occupied property.

Pros:

• Rental income continues through closing
• No vacancy gap between your ownership and the sale
• Tenant maintains the property's lived-in condition

Cons:

• Significantly limited buyer pool (most owner-occupants will not buy with a tenant in place)
• Harder to coordinate showings around tenant's schedule
• Tenant may not cooperate or may not keep the property show-ready
• Financing complications for buyers (some lenders have restrictions on tenant-occupied purchases)

Option 3: Sell to a Cash Investor with Tenants in Place

This is where the tired landlord equation often works best. Cash investors, particularly buy-and-hold investors, actively seek tenant-occupied properties.

Pros:

• Fastest path to closing, often 7 to 21 days
• Tenant stays in place with no disruption
• No vacancy period, no turnover costs
• Investor wants the tenant because it means immediate income
• No repairs, staging, or showing preparations needed
• No financing contingencies or appraisal risk

Cons:

• Sale price may be below full retail market value
• Need to vet investors carefully to ensure they will close

Option 4: Evict Tenants, Renovate, Then Sell

If the property needs significant updating and you believe a renovated, vacant home will command a substantially higher price, this may be worth considering.

Pros:

• Highest potential sale price
• Property appeals to the broadest buyer pool
• You control the condition and presentation

Cons:

• Eviction in Florida is expensive ($1,500-$5,000+ in legal fees) and time-consuming (30-90 days minimum)
• Renovation costs have increased 20-30% since 2020
• Contractor availability remains challenging in many Florida markets
• Legal risk if eviction is not handled properly
• Months of additional holding costs during renovation
• No guarantee the renovation investment will be fully recouped

Why Cash Investors Want Tenant-Occupied Properties

It may seem counterintuitive, but many real estate investors specifically seek out properties with tenants already in place. Understanding why helps you see the value in what you are selling.

Immediate Cash Flow from Day One

An investor who buys a vacant property needs to find a tenant before collecting any rent. That means marketing the property, screening applicants, executing a lease, and possibly waiting 30-60 days before the first rent check arrives. A tenant-occupied property produces income from the day of closing.

No Vacancy Period

Vacancy is the silent killer of rental property returns. Even one month of vacancy per year reduces annual income by 8.3%. Buy-and-hold investors understand this math intimately, which is why a property with a performing tenant (one who pays on time) is actually worth more to them than a vacant unit.

Built-In Income Stream with Documentation

When you sell a tenant-occupied property, you can provide rent rolls, payment history, and lease terms that prove the income stream. This documentation is valuable to investors, especially those using bank financing or portfolio lenders, because it demonstrates the property's actual (not projected) income potential.

Buy-and-Hold Investors Specifically Seek These Deals

Florida's rental market continues to attract buy-and-hold investors from across the country. These buyers are not looking for fixer-uppers to flip. They want stabilized, income-producing assets they can hold for years. Your tired landlord situation is their ideal acquisition. They have the systems, scale, and management infrastructure to handle what exhausts individual owners.

Tax Implications of Selling a Florida Rental

Selling a rental property has different tax consequences than selling your primary residence. Understanding these implications helps you plan for the true net proceeds and explore strategies to minimize your tax burden.

Capital Gains: Short-Term vs. Long-Term

If you have owned the property for more than one year, your profit qualifies for long-term capital gains rates, which are 0%, 15%, or 20% depending on your taxable income. Properties held for less than one year are taxed as ordinary income, which can be significantly higher. Most tired landlords have held their properties for several years, so long-term rates typically apply.

Depreciation Recapture (Section 1250)

This catches many landlords off guard. If you have been claiming depreciation on your rental property (and you should have been, as it is required even if you did not claim it), you will owe depreciation recapture tax on the portion of your gain attributable to depreciation deductions. This is taxed at a maximum rate of 25%, regardless of your income bracket. For a property you have depreciated over 10 years, this can represent a significant tax liability.

1031 Exchange: Deferring Your Taxes

A 1031 exchange (named after Section 1031 of the Internal Revenue Code) allows you to defer both capital gains and depreciation recapture taxes by reinvesting your sale proceeds into a like-kind investment property. The rules are strict:

• 45-day identification period: You must identify replacement properties within 45 days of closing
• 180-day closing deadline: You must close on the replacement property within 180 days
• Like-kind requirement: Must be investment real estate (not a primary residence)
• Qualified intermediary: A third-party must hold the funds; you cannot touch the money
• Equal or greater value: To defer all taxes, the replacement property must be equal to or greater in value

A 1031 exchange is particularly powerful if you are selling a Florida property and buying in another market where the investment thesis is stronger.

No Florida State Income Tax

One significant advantage of selling a Florida rental: there is no state income tax on your gain. In states like California (up to 13.3%) or New York (up to 10.9%), state taxes take a substantial additional bite. Florida sellers keep more of their proceeds, which is one reason the state attracts so many investors in the first place.

Net Investment Income Tax (3.8%)

If your modified adjusted gross income exceeds $200,000 (single) or $250,000 (married filing jointly), you may owe an additional 3.8% Net Investment Income Tax on your capital gains. This surtax applies to the lesser of your net investment income or the amount by which your MAGI exceeds the threshold.

How to Maximize Your Sale Price

Whether you sell on the MLS or to a cash investor, preparation matters. Here is how to position your property for the best possible price.

Get Competing Offers

The single most effective way to maximize your sale price is to create competition among buyers. A marketplace approach where multiple investors evaluate and bid on your property typically yields 10-15% more than accepting a single unsolicited offer. This is true whether you are selling one property or ten. Competition drives prices up and terms in your favor.

Provide Rent Rolls and Income Documentation

Investors evaluate rental properties based on income, not just comparable sales. Prepare the following documentation before soliciting offers:

• Current lease agreement with all terms and addenda
• Rent roll showing monthly payments for the past 12-24 months
• Tenant payment history (on-time percentage, any late payments)
• Current rent amount compared to market rent (is there room to increase?)
• Any pending rent increases or lease renewals

Document Maintenance and Capital Improvements

Buyers, especially sophisticated investors, want to understand the property's condition and what major systems have been updated. Compile records for:

• Roof age and any recent repairs or replacement
• HVAC system age, maintenance history, and last service date
• Plumbing and electrical updates
• Appliance ages and condition
• Any renovations or capital improvements with receipts
• Recent inspection reports

Highlight Location Advantages

Do not assume investors know your neighborhood. Provide context that supports property value and rental demand:

• Proximity to major employers, hospitals, or universities
• School district ratings
• Population and job growth data for the metro area
• Planned infrastructure improvements (new roads, transit, commercial development)
• Comparable rental rates in the area

Show Lease Terms and Tenant Quality

A strong tenant with a solid payment history is a genuine asset. Highlight the following:

• Tenant's length of tenancy (long-term tenants reduce turnover risk)
• On-time payment record
• Lease expiration date and renewal likelihood
• Whether the tenant has expressed interest in staying under new ownership

The Insurance Factor for Florida Landlords

No discussion of Florida rental property ownership in 2026 is complete without addressing the insurance crisis. This single factor has transformed the economics of landlording in the state.

Landlord Insurance Premiums Are Even Higher Than Homeowner Policies

While all Florida property owners have faced rising insurance costs, landlord policies carry an additional premium because the property is not owner-occupied. Non-owner-occupied properties are considered higher risk by insurers due to the additional liability exposure, less personal oversight of the property, and the tenant's behavior being outside the owner's direct control. Typical landlord policy premiums in Florida now range from $3,000 to $8,000+ per year for a standard single-family home, depending on location, age, and proximity to the coast.

Some Carriers Have Dropped Landlord Policies Entirely

Several major insurers have stopped writing new landlord policies in Florida or have exited the state's property insurance market altogether. This has pushed many landlords to Citizens Property Insurance, Florida's state-backed insurer of last resort, which is often more expensive than private market alternatives and imposes stricter requirements.

Impact on Investment Returns

Consider a property with these financials:

Despite a 16.7% rent increase over five years, net operating income dropped by 18.5%. After mortgage payments (which may have also increased if you refinanced at higher rates), many landlords are barely breaking even or losing money each month. Insurance is the primary driver.

Selling Multiple Properties

If you own two or more rental properties in Florida and are considering exiting the market, you have additional strategic considerations beyond what a single-property seller faces.

Portfolio Sales to a Single Investor

Selling your entire portfolio to one buyer has several advantages. You negotiate one deal, one closing, one set of transaction costs. Larger investors and institutional buyers specifically seek portfolio acquisitions because they achieve immediate scale. You may also have leverage to negotiate better terms when the total deal size is larger. A portfolio of five to ten performing rentals in a Florida metro area is a highly attractive acquisition for mid-size investment companies.

Tax Planning Considerations

Selling multiple properties in a single tax year concentrates your capital gains and depreciation recapture, potentially pushing you into higher tax brackets. A 1031 exchange becomes even more valuable at portfolio scale, but the logistics are more complex. Work with a tax advisor to model different scenarios. You may also want to explore an installment sale structure, where the buyer pays over time and you recognize gains incrementally.

Staggered vs. Bulk Approach

You do not have to sell everything at once. Consider the trade-offs:

• Bulk sale: One transaction, one closing, minimal ongoing obligation. May accept a slight discount for the convenience. Best if you want a clean exit.
• Staggered sales: Sell one or two properties per year to spread tax liability. Allows you to reinvest some proceeds via 1031 exchanges while cashing out on others. Best if you have time and want to optimize tax efficiency.
• Hybrid approach: Sell the underperformers now for cash, 1031 exchange the stronger properties into better markets or asset classes. Best for investors who want to rebalance rather than fully exit.

Disclaimer: This article is for informational purposes only and does not constitute legal, tax, or financial advice. Florida landlord-tenant law and tax regulations are subject to change. Consult a qualified attorney and CPA before making decisions about selling rental property. Data referenced reflects conditions as of February 2026.