CRM Platform

Vacation Rental CRM

Purpose-built for hospitality. Every guest, owner, and vendor lives in a unified CRM connected directly to your PMS. Multi-email contacts, custom fields, merge and dedup, verification, lifetime value, groups, tags, and a complete activity timeline, all designed around how vacation rental companies actually operate.

PMS Connected Guest Profiles Owner Management Custom Fields Contact Merge Multi-Email

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Vacation Rental CRM product interface preview

Built for vacation rental property managers

Every guest, owner, and vendor lives in one PMS-connected CRM. Reservation data drives marketing automation, AI Voice quotes accurate availability and rates from your PMS, the unified inbox threads Airbnb, SMS, email, WhatsApp, and voice against every record, and gap-night fill, owner statements, and homeowner acquisition workflows are first-class instead of bolted on.

Because SendSquared also serves hotel and resort operators, vacation rental property management companies on the platform inherit the operational discipline professional hotels run on — call-center workflows, group-booking pipelines, AI Voice trained on accurate rate-plan quoting, RevPAR-style attribution. As VR property management companies professionalize and elevate to hotel-grade standards, that rigor stops being optional and becomes a competitive advantage.

Also for: Hotel CRM → • Resort CRM →

PMS-Connected Guest Profiles

Guest profiles sync automatically from your property management system. Every contact carries their full reservation history, unit preferences, revenue totals, and stay dates. When a guest calls, messages, or books, your team sees their entire relationship with your company without switching systems.

Auto Sync

Syncs from Streamline, Barefoot, Guesty, Escapia, and more.

Stay History

Full reservation history with revenue, dates, units, and guest counts.

30+ Sources

Every contact source tracked — PMS, forms, WiFi, chat, and more.

External IDs

External ID mapping keeps PMS integration seamless across systems.

Multi-Email & Phone Management

Guests don't live in one inbox. SendSquared supports multiple email addresses per contact with primary designation, validation tracking, and error logging. Mobile and home phone numbers are stored separately. WhatsApp IDs and Airbnb IDs link to their respective messaging channels, giving you every way to reach a guest in one profile.

Multiple Emails

Multiple addresses per contact with primary selection and tracking.

Validation Tracking

SMTP-level validation with per-address error logging.

Mobile + Home

Mobile, home phone, and WhatsApp ID all on one profile.

Airbnb ID Link

Cross-platform guest ID linking for unified messaging.

Custom Fields

Capture exactly the data your business needs. Create unlimited custom fields with typed values like text, dropdowns, dates, currency, checkboxes, and more. Custom fields are available across contact profiles, segment conditions, automation triggers, and template merge tokens. Your PMS-specific data flows into custom fields automatically through connector integrations.

Unlimited Fields

Add as many custom fields as you need with typed values.

Segments & Workflows

Custom fields available in segments, automations, and merges.

PMS Data Mapping

PMS-specific data maps automatically through connectors.

Field Validation

Validation enforced on every create and update operation.

Contact Merge & Deduplication

When the same guest exists twice, whether from a different email, same phone, or imported from multiple sources, merge them into one clean profile. Select the primary contact, choose which fields to keep, and the secondary is soft-deleted. All reservation history, timeline entries, group memberships, and tags consolidate into the surviving record. Permission-controlled so only authorized team members can merge.

Field Selection

Pick which values to keep field-by-field during merge.

History Merges

Reservation history and timeline entries consolidate cleanly.

Groups & Tags

Group memberships, tags, and assets all carry forward.

ACL-Gated

Permission-gated with MergeContacts ACL for authorized users only.

Unified Activity Timeline

Every interaction across every channel lives on one timeline. Email, SMS, WhatsApp, Airbnb, voice calls, voicemails, notes, leads, reservations, surveys, tasks, and WiFi logins, all logged chronologically per contact. Filter by channel type, page through history with cursor-based pagination, and see who on your team handled each interaction.

12 Channel Types

Single chronological feed across every communication channel.

Direction Tracking

Inbound, outbound, and system events all flagged on entry.

Agent Attribution

Every timeline entry records the agent who handled it.

Filter & Paginate

Filter by channel and paginate through full contact history.

Groups, Tags & Segments

Organize contacts three ways. Standard groups hold static contact lists you build manually or via import. Dynamic segments re-evaluate automatically based on conditions like reservation data, contact properties, lead status, survey responses, campaign engagement, and more. Tags provide lightweight labels that trigger automations on add and remove. All three work together for precision targeting.

Static Groups

Manual groups with import capability for curated lists.

Dynamic Segments

Condition-based segments auto-sync on your schedule.

Smart Tags

Automation triggers fire on tag join and leave events.

Folder Organization

Folder system organizes groups, segments, and tags at scale.

Owner Management & Relations

Property owners aren't guests; they need their own relationship model. Assign agents as contact owners for relationship management. Link contacts to each other with labeled relationships like spouse, travel companion, and property owner. Track owner weeks and unit associations for timeshare operations. Every owner gets the same rich profile, timeline, and communication history as guests.

Agent Owners

Assign agents as contact owners for relationship management.

Contact Relations

Link contacts with labels like spouse, companion, owner.

Owner Weeks

Owner week and unit association tracking for timeshare ops.

Pacing Emails

Reservation pacing reports emailable directly to property owners.

Opt-In & Compliance Management

Per-channel do-not-contact flags protect your compliance. Each contact carries separate opt-out controls for email, SMS, WhatsApp, Airbnb, and AI routing, with reason tracking and timestamp logging. SMS requires explicit opt-in with a full opt-in/out history table. Email unsubscribes support per-brand scoping. Implicit SMS consent is configurable for reservation-based implied consent scenarios.

Per-Channel DNC

Separate do-not-contact flags per channel with reason tracking.

SMS History

Full SMS opt-in/out history with reason and timestamp.

Per-Brand Unsub

Per-brand email unsubscribe scoping for multi-brand ops.

Implicit Consent

Configurable implicit SMS consent for reservation-based messaging.

Import, Export & Search

Bring your data in and take it with you. CSV import with column mapping, duplicate handling, group assignment, and background processing. Export contacts filtered by groups and tags with async file generation. Universal search finds contacts by email, phone (auto-parsed to E.164), name, Airbnb ID, or confirmation code, with relevance scoring across multiple match types.

CSV Import

Column mapping, dedup handling, group assign, background processing.

Async Export

Filtered exports with download tracking for groups and tags.

Universal Search

Find by email, phone (E.164), name, Airbnb ID, or confirmation code.

Bulk Ops

Batch tag and group assignment up to 1,000 contacts at a time.

Guest Verification

Verify guest identity directly through your CRM or through digital guidebooks. Guests upload ID documents that are stored securely in S3 with access logging and audit trails. Agents review documents with role-based permissions, mark contacts as verified, and the blue check badge appears across the entire platform, including the inbox, call screen, lead records, and guidebooks.

Secure Upload

Encrypted S3 storage with access logging and audit trail.

Role-Based Review

Permissions gate viewing, uploading, and completing verification.

Blue Check Badge

Verified badge visible across every platform touchpoint.

Admin Removal

Only admins can remove a badge, with full audit trail.

Contact Lock & Security

Prevent accidental edits or deletions on critical contacts. Admin-only contact locking freezes a record with no field changes, no group modifications, and no deletion until an admin unlocks it. Combined with granular ACL permissions across 40+ operations, your team has exactly the access they need and nothing more.

Admin Lock

Freeze a contact so no edits or deletions happen until unlocked.

40+ ACL Permissions

Granular permission controls across every CRM operation.

Conversation ACLs

Assignment, reassignment, and close each permissioned separately.

Independent Controls

Verification, merge, and export permissions all gated separately.

Testimonials

What Our Clients Say

“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

“My experience with SendSquared has been eye opening. To be honest I didn't think something this good existed. Having all emails, texts, calls, web chat and marketing in one place has given my company and team a huge advantage. SendSquared has saved us both time and money which are very important factors to my small business of 50 luxury homes. The company is amazing to work with and extremely helpful whenever it was needed.”

Jessica Goree

Chief Operations Officer, Beach Reunion

“SendSquared is a game-changer for our resort operation. Its ability to integrate with our reservation software, providing real-time reservation information during phone calls, allows us the opportunity to build off of the rapport we've already created with our repeat guests. We're answering phone calls asking our guests how their kid's baseball season went, instead of asking for their names.”

Tim Oxborough

Reservation Manager, Sugar Lake Lodge

“We manage over 300 properties and SendSquared has been instrumental in streamlining operations. Consolidating all communications into one platform while maintaining personalized guest experiences has been transformative for our team.”

Shawn Montgomery

Director of IT, Collins Vacation Rentals

“SendSquared is an indispensable tool for us! One of their significant standout attributes is its ability to centralize communication channels, offering a one-stop solution for managing various modes of interaction. This consolidation streamlines our workflows, enhancing our efficiency and productivity. What's better is their customer support elevates the user experience. Their responsive team is always ready to assist, going above and beyond to ensure seamless integration and utilization.”

Fred Cercena

CEO & Founder, GetAway Vacations

Read all client stories

Frequently Asked Questions

How is this different from a generic CRM?

Built specifically for hospitality with native PMS integration. Guest profiles include reservation history, lifetime value, stay preferences, and channel data - not just contact fields.

Does the CRM sync with my PMS?

Yes. Real-time PMS synchronization keeps guest profiles, reservation data, and property information current without manual imports.

Can I track guest preferences and history?

Yes. Every interaction across voice, email, SMS, WhatsApp, and Airbnb is logged. Past stays, preferences, notes, and tags build a complete guest profile.

Is there a mobile CRM app?

Yes. Full CRM access on iOS and Android with contact profiles, reservation details, communication history, and one-tap calling and texting.

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