Rabbithole is a San Juan firm that designs, builds and operates the automation behind boutique hotels in Puerto Rico: calls, the guest inbox, direct bookings, pre-arrival messages, review replies and follow-up after checkout. We build it around the tools you already use and run it for you on a monthly retainer.
It's not the rooms or the service. It's the calls, messages and follow-up that land on a small team at all hours.
A guest calls from the airport at 11 PM. Someone emails about late checkout. If nobody answers, they book somewhere else or arrive frustrated.
Parking, breakfast, check-in time, directions. Your staff answers them one at a time, by phone, email and every booking platform's inbox.
A visitor on your website with a question about rates or availability gets no answer, books through an OTA instead, and you pay the commission.
Google, TripAdvisor, Booking.com, Airbnb. Answering each one with care takes time the front desk doesn't have.
Every unanswered call and every email that waits until Monday is a booking that can go somewhere else. Your team isn't the problem. The repetitive work never stops.
Hotel software is a tool your staff has to learn and babysit. Infrastructure is the layer that sits on top of your hotel and does the work. Custom-built and operated end to end.
We build what your hotel needs and skip what it doesn't.
Free guides on how these pieces work: AI receptionist, inbox triage, review responder, customer follow-up.
Hotel Bahía Azul is a fictional hotel we built to show how the system works: the receptionist, the booking chat, review drafting and the pre-arrival messages. Every guest, booking and number in it is mock data. It is not a client.
Running two to four weeks after kickoff, then a monthly retainer.
We map how calls, emails, bookings and reviews move through your hotel today and find where guests and hours slip away.
We set up the receptionist, inbox, booking chat and guest messages around your hotel's own information and voice. Nothing for your staff to manage.
We run, monitor and improve everything on a monthly retainer. If something breaks, we fix it.
We run our own businesses on the same infrastructure we build for clients. What you get is what we use.
In person with hotels in Puerto Rico, remote with everyone else. Same team either way.
You talk to the people who build your system, not a junior account manager.
A monthly retainer, plus a one-time setup fee where the scope calls for it. Month to month. No surprise invoices.
No. Software is a tool your staff has to learn, configure and maintain. We build the workflows around your hotel and operate them for you. You see the results, not another dashboard to manage.
No. We build around the tools you already use and connect what can be connected. Which connections are possible depends on your systems, and we confirm that during the audit.
Yes. The receptionist, the booking chat and the guest messages work in both languages, and review replies are written in the reviewer's language.
It goes to a person. Every system we ship has escalation rules and a human in the loop where it matters, so a complaint, a special request or a bad review reaches you or your staff instead of getting an automatic answer.
It depends on scope. Some engagements are a flat monthly retainer that covers audit, build, deploy and operate. Others add a one-time setup fee for the build, plus the monthly retainer. Pricing is laid out before we start, with no surprise invoices. The retainer is month to month, with no long-term contract.
Audit in three days, then your systems built and live in two to four weeks from kickoff. If we're not running in your business within 30 days of kickoff, you don't pay your second month.
San Juan, Puerto Rico. We work in person with hotels here and remotely with hotels anywhere else. Same team and same access either way.
Thirty minutes with the founders to find the biggest bottleneck in your hotel and see what we would build to fix it. No pressure.
Calendar not loading? Book your 30-minute call here →