Updated
If you manage vacation rentals for their owners, every month ends the same way: one invoice per owner for your commission, a statement showing what their properties earned, and a spreadsheet to update. With ChatGPT or Claude connected to Nowistay and to your accounting software, this takes one message. The assistant reads the month’s bookings in Nowistay, applies each owner’s commission model, creates the invoices in your accounting software, writes the owner statements and fills in your tracking sheet. You check, then you send.
This guide follows a US property manager using QuickBooks Online. If you use other software or work in another country, see accounting software by country.
| Piece | What it brings |
|---|---|
| Nowistay | The month’s bookings with their amounts: total, cleaning fee, tourist tax and platform commission |
| A project in ChatGPT or Claude | Your owners, their billing details and each owner’s commission model, set up once |
| QuickBooks Online | Customers, invoice numbers, sending and payment tracking |
The assistant reads and calculates. QuickBooks issues the invoice. Nothing is sent until you ask for it.
A PDF written in a chat makes a good owner statement, but not a reliable invoice: nothing guarantees that its number follows the previous one, and it never reaches your books. When the assistant creates the invoice in QuickBooks instead, the invoice gets its QuickBooks number, shows in your receivables and is matched when the owner pays.
There is no federal invoice format in the US, but your records still have to add up at tax time:
The connection works with one QuickBooks company at a time. To work on another company, reconnect and choose it.
A project keeps your instructions and your owner sheet, so every chat you start in it already knows them.
Paste these instructions, with your own company details:
You prepare the monthly owner billing of Sunset Coast Rentals LLC, 450 Ocean Drive, Miami FL 33139.
- Bookings and amounts come from Nowistay only. Never estimate or invent an amount: if one is missing, list the booking and ask me.
- Owners, billing details and commission models are in owners.xlsx in this project. If a property or a rule is missing, ask me. Never guess.
- Invoices are created in QuickBooks: one invoice per owner and per month, one line per stay.
- Always show me the calculation table and wait for my OK before creating anything.
- Never send an invoice or an email unless I explicitly ask for it.
- Round each commission line to the cent. The total is the sum of the rounded lines.You don’t fill in a spreadsheet yourself. The assistant starts from your property list in Nowistay, asks you the questions and builds the sheet from your answers. In a new chat inside the project, send:
Let’s set up my owner billing. Read my properties in Nowistay. Then ask me, one property at a time, who the owner is (person or company), their billing address and email, and how my commission works for them. When a property probably works like the previous one (same owner, same contract), suggest the previous answers so I can just confirm. Then check the commission model on a real stay from last month and show me the calculation. When everything is confirmed, create owners.xlsx with one row per property.
The commission questions come in plain words, for example:
The assistant then checks that it understood, on a real booking: “Ocean View 2B, Airbnb, Oct 3 to 7, total $754: your commission would be $120.00. Is that right?” If the figure is wrong, say why and it corrects the rule.
Example of the sheet it builds:
| Property (as in Nowistay) | Owner | Billing address | Commission | Calculated on | Cleaning fee | A stay counts in | Notes |
|---|---|---|---|---|---|---|---|
| Ocean View 2B | Jane Miller | 18 Bay Rd, Tampa FL 33606 | 20% | Stay without cleaning fee | Kept by manager | Check-out month | |
| Ocean View 3A | Jane Miller | 18 Bay Rd, Tampa FL 33606 | 20% | Stay without cleaning fee | Kept by manager | Check-out month | |
| Palm Cottage | Miller Family Trust | 200 Main St, Sarasota FL 34236 | 18% | After platform commission, without cleaning fee | Kept by manager | Check-out month | Minimum $150 per month |
| Harbor Loft | Coastal Homes LLC | 75 Harbor Way, Miami FL 33131 | 25% | Whole stay, cleaning included | Paid to owner | Nights in each month | Direct bookings: 15% |
The real file also holds each owner’s email and payment terms.
Add the sheet to the project. Neither assistant saves a file into a project on its own: download owners.xlsx, then add it to the project’s files in ChatGPT, or with the + button of the project knowledge panel in Claude.
When something changes, say it in the project: “Palm Cottage goes to 20% from December” or “Add the owner of Bayfront Studio”. The assistant asks what it needs, gives you the updated owners.xlsx, and you replace the old file in the project.
With only 2 or 3 properties, you can skip the file: ask the assistant to write the table as text and paste it at the end of the project instructions.
| Amount | What it contains |
|---|---|
| Total amount | What the guest paid for the stay: accommodation, cleaning fee and tourist tax. A service fee the platform charges the guest is not included: it goes to the platform. |
| Cleaning fee | The booking’s cleaning fee. |
| Tourist tax | Occupancy and tourist taxes, whether the platform collects them or you do. |
| Platform commission | What Airbnb, Booking.com, Expedia or Agoda charge you, Booking.com payment fees included. None on direct bookings. |
| Accommodation | Not stored on its own: the total amount minus the cleaning fee and the tourist tax. |
An Airbnb stay of 4 nights at $150, with a $100 cleaning fee and $54 of occupancy tax collected by Airbnb. Airbnb’s commission on the booking is $108.50. Nowistay records a total amount of $754.
| Commission calculated on | Calculation | Base | 20% commission |
|---|---|---|---|
| The whole stay, cleaning included | total − tourist tax | $700.00 | $140.00 |
| The stay without the cleaning fee | total − cleaning fee − tourist tax | $600.00 | $120.00 |
| What is left after the platform, without the cleaning fee | total − cleaning fee − tourist tax − platform commission | $491.50 | $98.30 |
The tourist tax stays out of the base: it belongs to the city or the state, not to the owner or to you.
With the second base, and the cleaning fee kept for your cleaning team, the owner’s statement for this stay reads:
| Line | Amount |
|---|---|
| Airbnb payout (total − tourist tax − platform commission) | $591.50 |
| Cleaning fee kept for the cleaning team | −$100.00 |
| Management commission (20%) | −$120.00 |
| Due to the owner | $371.50 |
In a new chat inside the project, send:
Prepare the October 2026 owner billing.
- In Nowistay, read every stay of the properties in owners.xlsx that counts in October under each owner’s rule.
- Show me one table per owner: property, guest, channel, dates, nights, total amount, cleaning fee, tourist tax, platform commission, base and commission. Flag any stay with a missing or zero amount.
- Wait for my OK.
- In QuickBooks, create the owner as a customer if needed, then one invoice per owner dated October 31, due in 15 days, with one line per stay (“Management commission, Ocean View 2B, Oct 3-7, Airbnb”). Don’t send anything.
- Write each owner’s October statement as a PDF: stays, revenue, platform commission, cleaning, my commission with its QuickBooks invoice number, and the amount due to the owner.
You get:
When everything is right, send the invoices from QuickBooks, or ask: “Send the October invoices to the owners.” Sending is always a separate request.
If you keep a monthly sheet of what each owner earned, the same chat can fill it. Give it your exact columns:
Give me October’s rows for my tracking sheet, with exactly these columns: Month, Owner, Property, Stays, Nights, Revenue, Platform commission, Cleaning, Commission, Invoice number, Due to owner. As an .xlsx file.
Then, depending on where your sheet lives:
Once a month has gone well by hand, you can schedule it. The scheduled run prepares everything: the calculation, the invoices in QuickBooks (not sent), the statements and the sheet rows. You check, then you send.
Write the scheduled task so that it works on its own, for example:
Prepare the previous month’s owner billing, following the instructions and the owners.xlsx sheet of my Owner billing project. Create the QuickBooks invoices without sending them, write the PDF statements, then send me a summary per owner, with every stay that has a missing amount.
Actions that create something in QuickBooks can wait for your approval during a scheduled run: approve them when you review the month, then check the first scheduled run closely.
Owners can connect their own ChatGPT or Claude to Nowistay, read-only, to see the bookings and monthly performance of their properties. See how to let property owners ask ChatGPT or Claude about their properties. When both sides read the same figures, questions about a statement are settled faster.
The situation in November 2026. An official connector is published by the software company itself. Connectors built by third parties send your accounting data through another company: prefer the official ones.
| Country | Software | Official connector | What the assistant can do | Good to know |
|---|---|---|---|---|
| United States | QuickBooks Online | ChatGPT and Claude | Create customers and invoices, send them on request | US customers only |
| United Kingdom | Zoho Books | Claude (directory), ChatGPT (custom connector) | Create and send invoices | Xero’s connectors only read data. Structured e-invoices required from April 2029 |
| France | Qonto | Claude (directory), ChatGPT (custom connector) | Draft, finalize, send invoices, including as e-invoices | Pennylane’s connector only reads data. E-invoicing reform from 2026 |
| Belgium | Odoo | Custom connector, to set up | Read and write records | Peppol e-invoices required between businesses since January 2026 |
| Germany | Qonto | Claude (directory), ChatGPT (custom connector) | Draft, finalize, send invoices (XRechnung, ZUGFeRD) | Lexware Office and sevDesk have no official connector. E-Rechnung between businesses from 2027 |
| Spain | Qonto | Claude (directory), ChatGPT (custom connector) | Draft, finalize, send invoices (VERI*FACTU) | Holded has no official connector. VERI*FACTU software required from 2027 |
| Italy | Qonto | Claude (directory), ChatGPT (custom connector) | Draft and finalize invoices | Every invoice must go through the SdI. Fatture in Cloud has no official connector |
| Netherlands | Moneybird | Claude (directory), ChatGPT (custom connector) | Create contacts and draft invoices, sent from Moneybird | No e-invoicing obligation yet |
| Portugal | InvoiceXpress | Claude (custom connector) | Issue certified invoices (ATCUD, QR code) | Invoices must come from certified software |
In Claude, a directory connector is added from Customize > Connectors. In ChatGPT, a custom connector is added after turning on developer mode in the settings, and creating or changing data through it depends on your plan: check yours.
They can write one, but a PDF made in a chat has no guaranteed numbering and doesn’t reach your books. In several countries (Italy, Portugal, and soon Spain, and France for business customers) an invoice must come from compliant software. Let the assistant calculate and prepare, and let your accounting software issue the invoice.
Only if your contract says so. Nowistay records the cleaning fee separately, so the assistant can include it or leave it out. Tell it once, when it interviews you, and it is saved in owners.xlsx.
The assistant makes one invoice per owner, with one line per stay, grouped by property. If you prefer one invoice per property, tell it during setup.
No. They are saved in owners.xlsx, in the project. You only update the sheet when an owner or a contract changes.
The connectors can send invoices, but keep sending as your own step: let the scheduled run prepare the invoices, then check and send them yourself.
On ChatGPT Business and Enterprise, and on Claude Team and Enterprise, your data is not used for training by default. On personal plans, turn off model training in the privacy settings. Nowistay only shares what each request needs, and guests’ contact details are left out unless you ask for them.
Guides for hosts: read the blog.
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