Key WestShort-term rental rules

Additional vacation and regional market / Florida

Key West separates transient rental licensing from nontransient rental activity and property-specific use rights.

Research reviewed Oct 31, 2026. Primary sources linked.

Compare this market What changed Start a property worksheet

Does the operating permit transfer?: Ownership update
Section 66-103 allows a business-license transfer after a bona fide business sale with evidence of sale, the original license, a transfer fee and written city-manager approval. The business tax receipt must transfer within 48 hours of closing. Confirm the separate transient-unit authorization and medallion record.
Can the land-use approval continue?: Verify the property approval
The operating-permit rule does not establish whether this parcel’s zoning approval, variance or older-use protection continues. Obtain the actual approval and its conditions.
Can this buyer obtain approval?: New transient licensing is constrained. Check the city transient-rental maps and the actual medallion record before assuming a unit can operate.
License or registration: Rental activity requires a city Business Tax Receipt. Transient operations also involve the city transient regulatory license or medallion framework.
Application availability: Confirm medallion and location
The city describes constraints on new transient licenses. Confirm the existing authorization and any transfer route; the map alone does not approve a buyer.
Timing to verify: Section 66-103(d) requires the business tax receipt transfer within 48 hours of closing. Arrange the documents and approval before closing.
Changes and uncertainty: Do not equate a nontransient rental registration with permission for nightly stays.

What this means for the appraisal

Obtain written confirmation of the ownership-update procedure and any required filings before assuming uninterrupted operation.
Verify the property’s land-use approval and continuation conditions. Research finding: Verify the property approval.
Check the proposed buyer against the recorded requirements: New transient licensing is constrained. Check the city transient-rental maps and the actual medallion record before assuming a unit can operate.
In the assignment analysis, identify the evidence supporting the proposed rental use, any operating interruption and any unresolved assumptions.

Use these prompts to plan the property review. The appraiser must evaluate the evidence and reach the assignment-specific conclusions.

Record the property evidence in a worksheet

Request documents from the owner or agent

Copy this market-specific request, add the property address and edit it for the assignment.

Read or select the document request

Document request for Key West

Subject: STR property document request | Key West, FL

Please provide the following documents for the property under review. Identify any item that is unavailable or does not apply.

1. Property address, parcel ID and confirmation of the governing jurisdiction.
2. Current operating permit or registration, named holder, expiration date and renewal history, if applicable.
3. Written ownership-change instructions from the issuing office. Guide finding: Section 66-103 allows a business-license transfer after a bona fide business sale with evidence of sale, the original license, a transfer fee and written city-manager approval. The business tax receipt must transfer within 48 hours of closing. Confirm the separate transient-unit authorization and medallion record.
4. Zoning approval, conditional-use permit, variance or grandfathering record, including conditions and evidence of continued use. Guide finding: The operating-permit rule does not establish whether this parcel’s zoning approval, variance or older-use protection continues. Obtain the actual approval and its conditions.
5. Documents addressing the proposed buyer and property requirements: New transient licensing is constrained. Check the city transient-rental maps and the actual medallion record before assuming a unit can operate.
6. Current confirmation of application availability, including any cap, waitlist, lottery or separation rule. Guide finding: The city describes constraints on new transient licenses. Confirm the existing authorization and any transfer route; the map alone does not approve a buyer.
7. Recorded covenants, HOA or condominium rental restrictions and applicable lease restrictions.
8. Rental operating statements and booking records, with the periods covered and any anticipated interruption at closing.
9. Confirmation of the applicable deadline and filing evidence: Section 66-103(d) requires the business tax receipt transfer within 48 hours of closing. Arrange the documents and approval before closing.
10. Written clarification: Confirm the transient-unit authorization and any medallion-specific buyer requirements. The city form for relocating a transient license between addresses is a different transaction from selling the same property.

Market research reviewed: 2026-10-31. These requests need property-specific verification.
Official research sources:
Key West official FAQs: https://www.cityofkeywest-fl.gov/m/faq
Key West regulatory licenses: https://www.cityofkeywest-fl.gov/1253/Regulatory-Licenses
Key West GIS, transient-rental and transfer maps: https://www.cityofkeywest-fl.gov/814/Geographic-Information-Systems-GIS-Divis
Key West code, section 66-103, business-license transfers and closing deadline: https://library.municode.com/fl/key_west/codes/code_of_ordinances?nodeId=SPAGEOR_CH66TA_ARTIVBUTA

Subject: STR property document request | Key West, FL

Please provide the following documents for the property under review. Identify any item that is unavailable or does not apply.

1. Property address, parcel ID and confirmation of the governing jurisdiction.
2. Current operating permit or registration, named holder, expiration date and renewal history, if applicable.
3. Written ownership-change instructions from the issuing office. Guide finding: Section 66-103 allows a business-license transfer after a bona fide business sale with evidence of sale, the original license, a transfer fee and written city-manager approval. The business tax receipt must transfer within 48 hours of closing. Confirm the separate transient-unit authorization and medallion record.
4. Zoning approval, conditional-use permit, variance or grandfathering record, including conditions and evidence of continued use. Guide finding: The operating-permit rule does not establish whether this parcel’s zoning approval, variance or older-use protection continues. Obtain the actual approval and its conditions.
5. Documents addressing the proposed buyer and property requirements: New transient licensing is constrained. Check the city transient-rental maps and the actual medallion record before assuming a unit can operate.
6. Current confirmation of application availability, including any cap, waitlist, lottery or separation rule. Guide finding: The city describes constraints on new transient licenses. Confirm the existing authorization and any transfer route; the map alone does not approve a buyer.
7. Recorded covenants, HOA or condominium rental restrictions and applicable lease restrictions.
8. Rental operating statements and booking records, with the periods covered and any anticipated interruption at closing.
9. Confirmation of the applicable deadline and filing evidence: Section 66-103(d) requires the business tax receipt transfer within 48 hours of closing. Arrange the documents and approval before closing.
10. Written clarification: Confirm the transient-unit authorization and any medallion-specific buyer requirements. The city form for relocating a transient license between addresses is a different transaction from selling the same property.

Market research reviewed: 2026-10-31. These requests need property-specific verification.
Official research sources:
Key West official FAQs: https://www.cityofkeywest-fl.gov/m/faq
Key West regulatory licenses: https://www.cityofkeywest-fl.gov/1253/Regulatory-Licenses
Key West GIS, transient-rental and transfer maps: https://www.cityofkeywest-fl.gov/814/Geographic-Information-Systems-GIS-Divis
Key West code, section 66-103, business-license transfers and closing deadline: https://library.municode.com/fl/key_west/codes/code_of_ordinances?nodeId=SPAGEOR_CH66TA_ARTIVBUTA

Research and guide updates

Oct 31, 2026 Research record: Research recorded for this market. Primary sources linked. See the findings, open questions and official sources below.
Nov 1, 2026 Guide tools: Added assignment prompts, a document request and consistent research questions. This tool update does not change the market research date.

Changes and uncertainty to verify

Do not equate a nontransient rental registration with permission for nightly stays.

Still to confirm

Confirm the transient-unit authorization and any medallion-specific buyer requirements. The city form for relocating a transient license between addresses is a different transaction from selling the same property.

Sources and research limits

The sale summary cites official code, program guidance or a court record. Read its scope and any remaining questions; it is not a parcel determination.

Use this summary to identify the documents and questions for a property review. A seller's rental history alone does not establish a buyer's permission to operate.

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