Two-Way Direct Connection
Guesty SendSquared Integration for Vacation Rentals
The only integration with true two-way message sync. Every message sent and received in SendSquared automatically shows up in Guesty, giving your team one place to work while keeping both systems in perfect sync. A connected vacation rental CRM, real-time data, bi-directional messaging, and full automation across SMS, email, WhatsApp, and voice.
Two-Way
Bi-Directional Message Sync
Real-Time
Reservation & Guest Data
6 Channels
SMS, Email, WhatsApp, Airbnb, VRBO, Voice
Two-Way Message Sync
Every message sent or received in SendSquared automatically appears in Guesty, and vice versa. Your team works in SendSquared's Unified Inbox while Guesty stays fully up to date. No copy-pasting, no missed messages, no gaps in the conversation history.
- Messages sent in SendSquared's unified inbox sync to Guesty automatically
- Inbound guest replies visible in both platforms instantly
- Email, SMS, WhatsApp, Airbnb, VRBO, and Booking.com channels
- Complete conversation history in Guesty without manual effort
Elegant Emails Powered by Guesty Data
Industry-standard email editor with drag-and-drop interface for building responsive emails using content blocks. Maintain property data from Guesty in every campaign for deeply personalized guest communication.
- Drag-and-drop editor with responsive design
- Native Guesty property data tokens for personalization
- Bi-directional data flow keeps contacts in sync
- Professional email design powered by live PMS data
Automate the Entire Guest Journey
Sync real-time data for seamless communication across the guest journey. From booking confirmations to post-stay follow-ups, every touchpoint is automated with timely, personalized messaging powered by Guesty's two-way direct connection.
- Booking confirmations to post-stay follow-ups automated
- Real-time data sync powers every automation
- Personalized messaging across the full guest journey
- Two-way direct connection ensures data accuracy
Already on Guesty? Get Connected in Minutes
Our two-way integration is the only one that syncs messages back to Guesty automatically. See it working live.
Testimonials
What Our Clients Say
“SendSquared is the second most important thing in our company outside of our PMS. All of our departments use it. Everyone in the company uses SendSquared. The engagement is what keeps us so well connected, and we are adding on average 10 doors a month at this point.”
Steven Wood
Founder, Host and Home
“SendSquared took everything we relied on and made it better, easier to use, and more centralized. Having everything in one platform has been a major improvement for our team.”
Mark Ryan
Revenue Manager, Wilderness Resorts & Waterparks
“In typical SendSquared fashion, it was easier than I expected.”
Brendan Curtin
CMK Development, Sailrock South Caicos
“The SendSquared tape chart has been our lifeline on the road. I used to print the calendar before heading out — now everything is right there, even with last-minute changes.”
Kim Collin
, Caribbean Villas of St. John
“I can definitely attribute a good number of reservations to SendSquared. Between the easy follow-up communication within the system and the CRM pulling up information as a call comes in, our reservations team is being more intentional on their calls, resulting in better conversions.”
Brock Reich
Chief Operating Officer, Orlando Resorts Rental
Frequently Asked Questions
How does the Guesty integration work?
Real-time synchronization pulls reservation data, guest profiles, and property details from Guesty into SendSquared for marketing, automation, and CRM.
Is reservation data synced in real time?
Yes. Reservation updates, new bookings, cancellations, and guest data sync automatically without manual imports or CSV files.
Can I segment guests using Guesty data?
Yes. All Guesty reservation fields - dates, revenue, unit types, booking channels - are available as segment conditions for targeted campaigns.
Does the integration support multi-channel bookings?
Yes. Reservations from all channels managed through Guesty (Airbnb, VRBO, direct) sync into SendSquared with source attribution.
Searching for a "Guesty CRM"? Guesty handles vacation rental operations: reservations, channel management across Airbnb / VRBO / Booking.com, and multi-unit portfolio coordination. SendSquared adds the layer it wasn't built for: vacation rental CRM with PMS-connected guest profiles, unified inbox threading SMS, WhatsApp, email, and voice into one thread per guest, PMS-powered email marketing with revenue attribution, AI voice agents answering inbound calls with live Guesty reservation context, and hotel messaging across every channel. Use Guesty for operations; layer SendSquared on top for the guest relationship.
Ready to Get Started?
See how SendSquared can transform your hospitality operations.
Schedule a DemoThe unified inbox is one piece of SendSquared's hotel messaging stack, with every channel (SMS, WhatsApp, Airbnb, email, voice) threaded against one PMS-linked guest profile.