Do You Get a 1099 for Collecting Retreat Payments? What the 1099-K Means for Hosts

This guide explains how the 1099-K works for retreat hosts. It is not tax advice. Thresholds and rules change, and your situation is specific — confirm anything you rely on with a CPA and the IRS's Form 1099-K guidance.

TL;DR:

• If your guests pay by card through Stripe or Square and you pass $20,000 in gross payments and 200 transactions in a calendar year, the processor files a 1099-K and sends you a copy. That is the federal rule since the 2025 tax law made it permanent; a few states set lower bars.
• The 1099-K reports gross: every dollar guests paid, before the venue, meals, facilitators and insurance. It is a payment report, not a tax bill.
• You are taxed on the profit: gross, minus your documented expenses. Collect $32,000, spend $25,200, and the taxable amount is $6,800.
• The form arrives from your processor, not from SquadTrip — payments settle into your own Stripe or Square account.
• The fix for tax-season dread is records: one business payment flow, an export that ties each payment to a guest, and the venue and vendor invoices in the same folder.

Yes — if you collect retreat payments by card through a payment processor and your gross payments for the year exceed $20,000 across more than 200 transactions, you will receive a Form 1099-K from that processor, and the IRS receives a copy. The form reports the total your guests paid. It does not report your income, because it knows nothing about the villa you paid for, the chef, the transfers or the insurance. Those come off first, and you pay tax on what is left. Hosts who use SquadTrip get the form from Stripe or Square directly, because guest payments settle into the host's own processor account.

That distinction — gross on the form, tax on the gain — is the whole subject, and it is the reason a host who took in $30,000 for a retreat and cleared $6,000 should not be frightened by a document that says $30,000. Here is how it works, when it applies, and how to make it a non-event.

What a 1099-K Actually Is

1. A report of gross payments

Form 1099-K is filed by a payment settlement entity — a card processor or a third-party payment app — reporting the gross amount of card and app payments it processed for you in the year. "Gross" means before refunds, before fees, before any of your costs. The IRS's own guidance is explicit that the form shows payments received, not taxable income.

2. Filed by the processor, not the platform

The entity that moves the money files the form. On SquadTrip, guest payments run through Stripe Connect or Square and settle into an account in your name, so the filer is Stripe or Square and the payee is you. SquadTrip never holds your funds and is not the settlement entity. Stripe's 1099-K documentation sets out the federal threshold it files against and the state-by-state rules.

3. The IRS gets a copy

The point of the form is matching: the IRS expects to see at least that gross figure somewhere on your return. Report it, then deduct — the gross appears, the expenses appear, the profit is what is taxed.

The Threshold, and When You Cross It

1. The federal number

For payments made in 2025 and later, the reporting threshold is more than $20,000 in gross payments AND more than 200 transactions in the year, both conditions together. The 2025 tax law (the One Big Beautiful Bill Act) restored that threshold permanently after several years of announced-then-delayed lower limits, so the $600 figure you may have read about no longer applies at the federal level. The IRS 1099-K FAQs are the primary source.

2. State thresholds can be lower

Several states set their own lower reporting thresholds, so a host below the federal bar can still receive a form because of where they live. Per Stripe's 1099-K state requirements table: Massachusetts, Maryland, Vermont, Virginia, Montana and the District of Columbia at $600; Illinois at $1,000 and 4 transactions; New Jersey at $1,000; Arkansas at $2,500. Most other states follow the federal threshold. Check your state revenue department's guidance for the current year.

3. A worked example

• 16 guests × $2,000 retreat = $32,000 gross — over $20,000
• Each guest pays a deposit and three instalments = 64 transactions — under 200

On the federal rule alone, this host would not cross both bars from one retreat; run two or three retreats a year, or sell add-ons, and the transaction count climbs quickly. Either way, the number on the form would be the gross, and the tax question would be the same.

A 1099-K Is Not Your Income

1. What comes off first

Everything it cost to run the retreat is deductible against the gross:

• Venue or accommodation
• Meals, chef, catering
• Facilitators and assistants
• Airport transfers and transport
• Retreat insurance
• Marketing, photography, design
• Materials, welcome gifts
• Payment processing you paid (on SquadTrip the 6% fee is paid by the guest on top of the price, so it is not your cost)

2. The netting, with numbers

The form says $32,000. The return says $32,000 in, $25,200 out, $6,800 taxable. Nobody pays tax on the $32,000.

3. Why records matter more than the form

The 1099-K arrives whether or not you kept receipts. The deductions only survive if you can show them. The host who exports every booking and files every invoice pays tax on $6,800; the host who cannot document the villa pays tax on far more.

Three Situations Hosts Ask About

1. "I'm just passing money through to the venue"

The gross still goes on the form, because the processor cannot see what the money was for. On your return the venue is an expense against it. If the venue was $9,000 and you collected exactly $9,000 to cover it, the netted result is zero — but only if the invoice is in the folder.

2. "Some guests paid me on Venmo instead"

Peer-to-peer apps can issue 1099-Ks too, and payments into a personal account are harder to tie to a business with expenses. Mixed flows are where hosts lose deductions. One business payment flow, one export.

3. "I run two retreats a year — is this a business?"

Regular, profit-seeking activity generally is, and that is good news: businesses deduct expenses. Whether you report on a Schedule C, whether an LLC or S-corp is worth it, and how self-employment tax applies are questions for a CPA — and they are much easier questions when the numbers are already reconciled.

Every guest payment on one flow, every payout exported. SquadTrip keeps the booking record behind each payment so the 1099-K reconciles in an hour.

How to Make Tax Season Boring

1. Use one business payment flow. All guest payments through your booking page into your own Stripe or Square account — no side payments to personal apps.
2. Open a separate bank account for retreat income and expenses, even without an LLC.
3. Export the year from SquadTrip and from your processor: bookings, instalments, refunds, payouts. The gross on the export should match the 1099-K.
4. File every invoice next to the export: venue, chef, facilitators, transfers, insurance, marketing.
5. Price with tax in mind. How to price a retreat and what a retreat costs to run both assume a margin; your margin is what gets taxed, so know it before you set the price.
6. Book the CPA in January, with the export and the folder, not in April with a shoebox.

Fact vs Myth

Final Thoughts

A 1099-K is a receipt for the year, sent to you and the IRS by the company that processed your cards. It says what came in. Your return says what went out, and you pay tax on the difference. Keep every guest payment on one business flow with a booking behind it, keep the invoices, and the form is administration, not alarm.

For the money side of hosting from the beginning, see how to host a retreat and the retreat cash-flow problem — the sequencing that keeps the venue deposit off your personal card.

Collect retreat payments the way your accountant wishes you would. Start free on SquadTrip — deposits, payment plans and a clean export at year end.