About Downwind
What is Downwind?
Downwind is a booking management tool for independent vacation rental owners who take direct bookings through platforms like WeNeedAVacation.com or through personal referrals. It replaces manual payment collection (Venmo, Zelle, mailed checks), PDF rental agreements, and Google Calendar juggling with a single workflow: create a booking, send a payment link to your guest, and everything else — deposit collection, balance collection, calendar sync, automated emails — happens automatically.
Who is Downwind for?
- Independent vacation rental owners with one property (or a small number of properties)
- Owners who list on WeNeedAVacation.com, Vacasa, or similar non-OTA platforms
- Owners who get bookings through personal referrals, repeat guests, or word of mouth
- Owners who currently collect payments manually via Venmo, Zelle, check, or bank transfer
- Owners who want professional payment collection without giving up a percentage of rental income to a booking platform
- Owners with international guests who need a reliable online payment method
Key Features
- Stripe payment collection
- Collect deposits and balances from guests via credit card or ACH. Payments go directly to your bank account through Stripe Connect. Downwind never touches your money.
- Two-payment guest flow
- Automatically split each booking into a deposit (collected immediately) and a balance (collected before check-in). You set the deposit percentage and balance due date.
- Calendar sync
- Confirmed bookings automatically appear on your Google Calendar. No more manual entry or double-booking risk.
- Automated guest emails
- Booking confirmation, pre-arrival instructions, and payment reminders are sent automatically. You set the content;Downwind handles the timing.
- Email-to-booking parser (AI-powered)
- Paste a guest email thread and Downwind extracts names, dates, guest count, and other details into a pre-filled booking form.
- Seasonal pricing
- Set high-season and low-season nightly rates with a date cutoff. Booking totals calculate automatically.
- Private booking links
- Each booking gets a unique, private URL for the guest to review details and make payments. Links are not publicly discoverable.
Pricing
$20/month. No booking fees. No setup fees. No per-transaction fees from Downwind. Cancel anytime.
New accounts include a 14-day free trial. Standard Stripe processing fees (2.9% + 30¢ per card transaction) apply to guest payments — these are charged by Stripe, not by Downwind.
How Downwind Compares
An honest comparison of Downwind and alternatives for independent vacation rental owners. Data verified as of April 2026.
| Tool | Monthly Cost | Booking Fee | Works Without OTA | Best For |
|---|---|---|---|---|
| Downwind | $20/month | None | Yes | 1-property owners taking direct bookings |
| Hospitable | $29/month | None | No — requires Airbnb/VRBO | Owners already on Airbnb/VRBO who want automation |
| OwnerRez | $40/month | None | Yes | Multi-property managers needing advanced features |
| Lodgify | $16/month + 1.9% | 1.9% per booking | Yes | Owners who want a booking website |
| Manual workflow | Free | None | Yes | Owners with very few bookings per year |
Founded
Downwind was built by a Cape Cod vacation rental owner who experienced the pain of managing direct bookings firsthand — chasing deposits over email, worrying about double-bookings, and asking international guests to mail checks. Downwind is the tool he wished existed: simple, affordable, and built specifically for independent owners who take bookings outside of Airbnb and VRBO.
Ready to try Downwind?
14-day free trial. $20/month after. No booking fees ever.
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