About Downwind

What is Downwind?

Downwind is booking software for vacation rental owners who take their own bookings. It isn't a listing site, and it isn't a property manager. It's everything that comes after a guest gets in touch: the rental agreement, the deposit, the balance, the guest emails, and the calendar.

You create the booking and the guest gets a link from us. They open it, read and sign the agreement, and pay online. The deposit and the balance both get collected, the confirmation emails send themselves, and the dates show up on your calendar.

It doesn't care where your bookings come from. Whether a guest found your listing on Facebook, stayed with you last summer after booking on Airbnb and wants to return, or heard about you from a friend, Downwind picks things up from the inquiry. Keep listing wherever you already do.

Who is Downwind for?

• Owners with one property, or a few
• Owners who list on a vacation rental site but keep the booking itself direct
• Owners on Airbnb, Vrbo, or Vacasa who want to run their own rebooking, so a guest who stayed once comes back to you and not to the platform
• Owners whose guests come from repeat stays and word of mouth
• Owners collecting money by check, PayPal, Zelle, or bank transfer right now
• Owners who don't want to hand a platform a cut of every booking
• Owners with guests overseas who need an easier way to pay

What it does

Paste emails, get bookings

Drop in the email thread from a guest and Downwind pulls out the names, the dates, rate and more into a booking form. Hit create and the guest gets a confirmation and a walkthrough of next steps.

One link for the guest

Every booking gets its own private link. The guest opens it, signs the agreement, and pays. No account and no app, and the link isn't indexed anywhere.

Guests pay online

By card or bank transfer, through our payment provider Stripe. The money and guest payment info go to your own account; they never pass through Downwind.

A deposit, then the balance

Each booking can split in two. You set the deposit amount and whether it's a security deposit or a first payment toward the rent. Downwind collects the balance before check-in and gives the guest longer to pay when the stay is further out.

One calendar

Confirmed bookings show up on your Google or Outlook calendar, so you aren't keeping your dates in two places and hoping they agree.

Refunds, returns and deductions

If you take security deposits, refund them after the stay with one click. You can withhold some of the money for damages, if it comes to it. We don't control your money decisions.

Pricing

$20 a month, flat. No booking fees, no setup fees, and no cut of anything your guests pay. Cancel whenever you want.

New accounts get 14 days free. Stripe charges its own processing fee on guest payments, around 2.9% + 30¢ on a US card and more on a card from abroad. Bank transfers are cheaper. That fee is Stripe's, not Downwind's.

How Downwind compares

There are really four ways to run a rental: a spreadsheet, one of the big platforms, a bookkeeping app, or this. I put them side by side on what they cost, who ends up owning your guests, and how much of your week they take, over on the comparison page.

Why I built it

My family owned a house on Cape Cod and we rented it out ourselves. The guests were never the problem. The busywork and accounts receivable side was: people mailing checks (sometimes unsigned), printing out rental agreements and mailing them across the country, chasing down payments, guests in Canada and Europe who took weeks to figure out HOW to even pay. And every so often a check would turn up and I'd forget to send the confirmation.

We sold the house in early 2026. I put the time I got back into building something I would have happily paid for: one place where the guest reads the agreement, signs it, and pays, with me only as involved as I wanted to be.