Key West, FL Rental Regulations Guide 2025

7 Step Guide to Key West Short-Term Rental Regulations

1. City Overview: Short-Term Rental Landscape

Key West, Florida, has strict regulations governing short-term rentals (STRs) to protect the residential character of the community. STRs, referred to as vacation rentals, are heavily regulated, and only properties within designated zones may operate legally. Monroe County also enforces additional rules outside of Key West city limits.

For the most up-to-date short-term rental data, including occupancy rates, average daily rates, and revenue trends, visit the Chalet Market Dashboard.

2. Quick Facts

  • Permit Required? Yes, a Vacation Rental Permit is required.
  • Zoning Restrictions? STRs are only allowed in specific zoning districts; restrictions apply.
  • Maximum Occupancy: Defined by zoning rules and property classification.
  • Tax Requirements: STR operators must collect and remit city, county, and state lodging taxes (11%)
  • Renewal Frequency: Annual renewal required for the Vacation Rental Permit.
  • Registration Fees:
    • Initial Vacation Rental Permit: $500
    • Annual Renewal Fee: $200
    • Local Business Tax Receipt: Fee varies by property classification
  • Insurance Required? Strongly recommended for liability protection.
  • Enforcement Level: Active enforcement, including fines for non-compliance.

3. Getting Started with STRs in Key West (Step-by-Step Guide)

Step 1: Verify Zoning Compliance

Before applying for a Vacation Rental Permit, property owners must confirm that their property is located in an eligible zoning district.

Step 2: Obtain a Vacation Rental Permit

All STR operators must obtain a Vacation Rental Permit from Monroe County before renting their property.

  • Permit Fees:
    • Initial Application: $500
    • Annual Renewal: $200
  • Required Documents:
    • Proof of property ownership
    • Floor plan indicating guest areas
    • Zoning compliance approval
    • Local Business Tax Receipt

Where to Apply:

Step 3: Register for Tax Collection & Payment

STR hosts must collect and remit applicable local and state lodging taxes.

  • Tax Registration Required With:
    • Monroe County Tax Collector
    • Florida Department of Revenue
  • Tax Rates:
    • Florida State Sales Tax: 6%
    • Monroe County Tourist Development Tax: 5%
    • Total Lodging Tax Rate: 11%
  • Filing and Payment Deadlines:
    • Taxes must be reported and paid monthly.
    • Payments are due by the 20th of each month for the previous month’s rentals.

Where to Register and Pay Taxes:

Failure to collect, report, and remit taxes can result in fines and penalties. Hosts are encouraged to maintain accurate records and consult a tax professional if needed.

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4. Regulatory Breakdown

Frequently Asked Questions provide detailed answers to the most common regulatory questions.

Example Questions:

  • Do I need a permit to operate an STR in Key West?
    • Yes, all STR operators must obtain a Vacation Rental Permit before listing their property.
  • What are the tax obligations for STR operators?
    • STRs are subject to local and state lodging taxes.
  • Are there zoning restrictions for STRs?
    • Yes, STRs are only allowed in certain zoning districts and must comply with Monroe County regulations.

Additional Resources:

Connect With Airbnb Agents
Connect With STR Lenders
Sell Your Airbnb
Airbnbs for 1031 Exchange

5. Key Considerations for Investors

  • Investment Potential: Key West remains a high-demand vacation rental market due to its tropical appeal and year-round tourism.
  • Regulatory Trends: Monroe County enforces strict vacation rental rules, and further restrictions may be implemented.
  • Community Compliance: STR operators should verify neighborhood-specific restrictions and remain updated on legislative changes.
  • More Information: Contact Monroe County Planning Department at (305) 809-3720 or visit the Chalet Market Dashboard.

6. Taxes and Financial Obligations

STR operators must register and remit taxes at the local and state levels.

Where to Register and Pay Taxes:

7. How Chalet Can Help

  • Local Realtor Partnerships:
    Looking to invest in short-term rental properties? Chalet’s nationwide network of specialized realtors is here to guide you. Our experts understand the nuances of vacation rentals and local markets, helping you identify high-ROI properties and navigate complex regulations with ease. Best of all, their services come at no extra cost to you. Click here to connect for free.
  • Chalet’s Regulation Updates:
    Chalet email subscribers receive updates regarding regulatory changes in cities. Subscribe here!
  • Connect with Local Experts:
    At Chalet, our goal is to enable everyone to create wealth with short-term rentals. We bring the experience and expertise to optimize your rental property. Connect with a STR professional in your area here.

Recommended Tools and Resources

  1. Chalet STR Market Insights Tool
    Chalet offers a free market analytics tool that allows investors to explore detailed data on occupancy rates, average daily rates, revenue estimates, and market trends for specific cities. This tool helps investors make informed decisions based on comprehensive insights. Access the STR Market Insights Tool.
  2. Airbnb Income Guide
    Investors can dive into this guide to better understand how to maximize income from STRs. It covers critical aspects such as dynamic pricing, guest management, and how to boost profitability through effective listing strategies. Read the Comprehensive Guide to Airbnb Income.
  3. Chalet Investor Guides
    These investor guides provide city-specific insights, including tax obligations, regulations, investment potential, and detailed market data. Investors can select from over 200 city guides to find data tailored to their target market. Explore Investor Guides.
  4. AI-Powered Market Comparison Dashboard
    Chalet’s market comparison dashboard offers a powerful tool for comparing different STR markets based on yield, occupancy rates, and other key performance indicators. This tool is particularly useful for investors looking to diversify across different regions. Check out the Market Dashboard.
  5. Chalet STR Calculator
    The free Chalet STR Calculator is a powerful tool designed to help short-term rental investors evaluate potential property performance with ease. It enables users to estimate revenue, analyze expenses, and project profitability for any STR market, streamlining investment decisions. Whether you’re comparing properties or exploring new opportunities, the Chalet STR Calculator simplifies the process with precision. Learn more about the Chalet STR Calculator.

DISCLAIMER: The information provided in these guides is for entertainment and general informational purposes only. It may not reflect the most up-to-date regulations, and Chalet is not responsible for any inaccuracies or changes to the information on third-party sites. These guides are not legal advice. We highly recommend verifying details directly with local authorities and consulting professionals before making any investment decisions. Ultimately, it is your responsibility as an investor to ensure compliance with local laws.

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