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SendSquared

Own Your Guest Journey. Drive Direct Revenue.·sendsquared.com

SendSquared is an AI-powered hospitality CRM and marketing platform built for vacation rental companies, hotels, and resorts. It integrates directly with property management systems to unify guest, owner, and lead communication into a single platform, covering the full guest lifecycle from lead capture through pre-arrival, in-stay, post-stay, and remarketing. The platform combines a unified inbox, AI voice agents, email and postcard marketing, lead management, guest surveys, digital guidebooks, WiFi capture, and reporting to help operators drive direct bookings.

What it's for

Lead capture and pipeline managementReservation salesPre-arrival guest communicationIn-stay guest engagementPost-stay surveys and review managementGuest loyalty remarketingOwner retention and acquisitionOTA-to-direct booking conversionCart abandonment recoveryGap night and shoulder-season fillMulti-channel guest messaging (SMS, email, WhatsApp, Airbnb, voice, chat)Call center operations and reportingGuest WiFi data capture

Features 20

AI Voice agents for sales and support modes
AI-powered website chat widget
Digital Guidebooks with PMS-synced content
Dynamic guest segmentation with 12 condition types
Enterprise call center with IVR, call recording, and voicemail transcription
Executive, agent, and revenue reporting suite
Guest ID verification with blue check badge
Guest WiFi captive portal for data capture
Homeowner acquisition and proforma tools
Lead management with pipeline kanban and automation
Lifetime value and predictive revenue analytics
Mobile apps for iOS and Android
Model Context Protocol (MCP) server for AI agent integration
Multi-channel automation workflows with conditional logic
NPS-based guest surveys with Z-score analysis
Official WhatsApp and Airbnb messaging integration
PMS-connected email marketing with Smart Send AI timing
Postcard and direct mail marketing
Task automation linked to messages
Unified Inbox across email, SMS, WhatsApp, Airbnb, and web chat

At a glance

API

TypeWeb app

DeploymentCloud

PlatformsWeb, iOS, Android

Forproperty management companies, vacation rental operators, hotels, resorts

CompanySendSquared · 2018

Integrations

BarefootStreamlineGuestyEscapiaRDPCloudbedsRoomKeyPMSHostawayLodgifyStayNTouchVisual OneVersaMaestroFullsteamOracle OPERAHomeRunnerGoogle TravelWhatsAppAirbnbClaudeChatGPTGrokGeminiLlamaMistralPerplexityDeepSeek

Complianceself-reported

GDPR CompliantISO-Aligned Security

Pricing

Pricing is based on the company's scale (units for rentals, keys for hotels); customers must contact sales for a customized quote. No free trial is offered, but demos are available.

SendSquared EnterpriseQuote

For vacation rentals and hotels focused on reservation sales; implementation typically takes six to eight weeks.

Pricing based on company scale (units for rentals, keys for hotels); custom quote required

SendSquared Owner EnterpriseQuote

For owner development and acquisition; implementation typically takes up to six weeks.

Pricing based on company scale; custom quote required