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Short-Term Rental (STR) Property Management Prompts

Short-Term Rental (STR) Property Management Prompts

Section titled “Short-Term Rental (STR) Property Management Prompts”

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4 ready-to-use prompts for prospecting long-term rental owners and converting them to short-term rental management

These prompts are designed for short-term rental (STR/Airbnb) property management companies that prospect landlords currently renting long-term on classifieds platforms.

Prerequisite: Have a ~/Cowork-Workspace/CLAUDE.md file with your local market calibration data (average nightly rate, occupancy rate, fees). See the STR property manager CLAUDE.md template.

Prospect Analysis Prompts

Section titled “Prospect Analysis Prompts”

1. Listing Analysis

Section titled “1. Listing Analysis”

Use for each listing manually copied from a classifieds platform (Le Bon Coin, Craigslist, Zillow, etc.).

CONTEXT: Check my file ~/Cowork-Workspace/CLAUDE.md for my market data and positioning.


Here is the listing to analyze:


[Paste the full listing text here: title, description, rent, area, location]


TASK: Analyze this property to assess its short-term rental potential.


OUTPUT:
1. Key information extraction
   - Property type (studio, 1BR, 2BR, 3BR+)
   - Approximate size (if mentioned)
   - Precise location (street, neighborhood, city)
   - Current long-term rental asking price
   - Strengths mentioned in the listing (view, parking, terrace, etc.)


2. Neighborhood analysis
   - Nearby tourist and economic assets (hotels, train stations, attractions, business districts)
   - Potential guest profile (tourists, business travelers, families)
   - 2 to 3 specific neighborhood elements I can mention in my outreach message


3. STR potential score (1 to 5)
   - 5: Very high potential (prime location, well-suited property)
   - 4: Good potential (several major advantages)
   - 3: Average potential (worth exploring based on costs)
   - 2: Limited potential (saturated market or unsuitable property)
   - 1: Not recommended (difficult area, oversized, prohibitive costs)


4. Talking points for the outreach message
   - Main reason this owner should consider STR
   - Differentiating neighborhood element to highlight


CONSTRAINTS: If the location is vague, mark the score as "to confirm." Do not invent advantages not mentioned in the listing or verifiable.


Save to: ~/Cowork-Workspace/output/prospects/[city]-[type]-[date]-analysis.md

2. STR vs Long-Term Revenue Estimate

Section titled “2. STR vs Long-Term Revenue Estimate”

Use after the listing analysis to calculate the potential gain for the owner switching from long-term to short-term rental with your management.

CONTEXT: Check my file ~/Cowork-Workspace/CLAUDE.md for my market calibration data (nightly rate, occupancy, costs).


Property details:
- Type: [Studio / 1BR / 2BR / 3BR+]
- Location: [neighborhood, city]
- Current long-term rent: $[X]/month
- Size: [X] sqft (if known)


TASK: Calculate a comparative monthly and annual revenue estimate.


OUTPUT: STR vs Long-Term Rental comparison table


**STR gross revenue (monthly)**
- Estimated nightly rate: $[based on my zone calibration data]
- Occupancy rate: [based on season]%
- Estimated nights booked/month: [calculation]
- Monthly gross revenue: $[calculation]


**STR costs to deduct (monthly)**
- Platform fee (3% host side): $[calculation]
- Cleaning ($[X] × [nb turnovers] turnovers): $[calculation]
- Linen and consumables ($[X]/stay): $[calculation]
- Tourist/occupancy tax (estimate): $[calculation]
- My management commission ([X]%): $[calculation]
- **Total costs**: $[calculation]


**Owner net STR revenue**: $[calculation]/month
**Current long-term rent**: $[X]/month
**Monthly gain from STR**: +$[calculation]/month (+[calculation]%)
**Annual gain**: +$[calculation]/year


CONSTRAINTS:
- Always use "estimated potential revenue" (never "guaranteed" or "assured")
- Specify data source (my calibration data from CLAUDE.md)
- If zone is not in my calibration data, indicate "estimate to be refined"
- Show high/low season ranges if occupancy rates vary significantly


Save to: ~/Cowork-Workspace/output/prospects/[city]-[type]-[date]-estimate.md

Prospect Communication Prompts

Section titled “Prospect Communication Prompts”

3. First Outreach Message

Section titled “3. First Outreach Message”

Use to write the personalized message sent to the owner after analyzing their listing.

CONTEXT: Check my file ~/Cowork-Workspace/CLAUDE.md for my communication tone and services.


Prospect data:
- Property type: [Studio / 1BR / 2BR / 3BR+], [size] sqft
- Location: [neighborhood + city]
- Long-term asking rent: $[X]/month
- Estimated STR net revenue: $[X]/month (based on my estimate)
- Neighborhood elements to mention: [the 2 points identified in the analysis]


TASK: Write a first outreach message for this property owner.


CONTENT CONSTRAINTS:
- Length: 150 to 200 words maximum
- Tone: professional but human, not aggressively salesy
- Approach: offer a free potential audit, not a direct pitch
- Mention revenue difference as "estimated potential revenue" (never "guaranteed")
- Reference at least 2 specific neighborhood or property elements
- Words to avoid: "guaranteed," "definitely," "for sure," "maximum returns"


MESSAGE STRUCTURE:
1. Opening tied to the property or neighborhood (1 sentence)
2. My positioning in one sentence (who I am, what I do)
3. Observation on the property's STR potential (with estimated gap, phrased carefully)
4. Concrete no-commitment proposal: a call or free audit
5. Brief, relaxed close


OUTPUT: The message ready to send, no generic intro or closing filler.


Save to: ~/Cowork-Workspace/output/prospects/[city]-[type]-[date]-message.txt

4. Property Owner Follow-Up Document

Section titled “4. Property Owner Follow-Up Document”

Use when an owner responds positively to the first outreach and wants to know more. Send as an attachment or share before a meeting.

CONTEXT: Check my file ~/Cowork-Workspace/CLAUDE.md for my services, fees, and positioning.


Property details:
- Owner: [First name] (if known)
- Type: [Studio / 1BR / 2BR / 3BR+], [size] sqft, [address or neighborhood]
- Current long-term rent: $[X]/month
- Estimated STR net revenue: $[X]/month (from my calculation)
- Specific elements to highlight: [property and neighborhood strengths from the analysis]


TASK: Write a 1 to 2 page follow-up document to send before or after a first call.


STRUCTURE:
1. Header
   - My company name + contact
   - "Prepared for [First name]" + date


2. Detailed STR vs Long-Term financial comparison for this property
   - Monthly and annual table (reuse the calculated estimate)
   - Explicit note: "Estimated potential revenue based on [zone] market data"


3. What I handle (services included)
   - List of services from my CLAUDE.md, reframed as owner benefits
   - Emphasize: zero management burden for the owner, monthly transparency, dynamic pricing


4. Legal framework simplified
   - STR is legal for non-primary residences without annual caps (check local regulations)
   - City/municipality registration may be required (I handle this)
   - Tax considerations (consult your accountant for your personal situation)


5. Next step
   - Proposal for a no-commitment walkthrough to finalize the estimate
   - Direct contact


CONSTRAINTS:
- Reassuring and factual tone (the owner is often new to STR)
- Zero promises of guaranteed revenue
- Maximum 2 pages
- Emphasize transparency (monthly report, reservation access)


Save to: ~/Cowork-Workspace/output/argumentaires/[city]-[type]-[date]-pitch.docx

Batch Processing

Section titled “Batch Processing”

To process multiple listings in the same session:

CONTEXT: Check my file ~/Cowork-Workspace/CLAUDE.md for my market data and tone.


I have [X] listings in ~/Cowork-Workspace/input/prospects/batch-[date]/.
Each file contains a listing manually copied from a classifieds platform.


TASK: For each listing, run the full analysis.


OUTPUT PER LISTING:
- Key information extracted
- STR potential score (1-5) with one-sentence justification
- Estimated owner net STR revenue vs listed long-term rent
- 2 neighborhood elements to use in the outreach message


FINAL SUMMARY:
Summary table of all listings:
File | Type | City/Neighborhood | Long-term Rent | Est. STR Revenue | Score | Priority


CONSTRAINTS:
- Sort by descending score in the summary
- Mark the top 3 prospects (score ≥4) with a star (★)
- If a file is unreadable or incomplete, mark "To verify" rather than guessing


Save:
- Analyses: ~/Cowork-Workspace/output/prospects/batch-[date]/
- Summary: ~/Cowork-Workspace/output/prospects/batch-[date]-summary.md

Customization Notes

Section titled “Customization Notes”

Priority placeholders to fill in CLAUDE.md:

  • Market calibration by zone (nightly rate, occupancy): this is what makes estimates relevant
  • Management commission: varies by positioning (15-25%)
  • Cleaning costs: based on your local service providers

Adjust tone to your positioning:

  • Premium STR management: emphasize luxury hospitality, business traveler clientele, Superhost status
  • Standard STR management: emphasize simplicity, transparency, value for money

On listing collection:

  • Use platform alert notifications (free, legal) to be notified of new listings matching your criteria
  • Manually copy the listing text into a .txt file (one file per listing)
  • Never automate collection: scraping violates platform Terms of Service and may be illegal

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