Top 4 Guest Messaging Software for Vacation Rental Managers

Lizzie Griffin
Lizzie Griffin

December 28, 2023

Questions about directions and parking, property and WiFi access, broken light bulbs, and leaky faucets can easily come to dominate your working week. Guest messages going unanswered impacts your reviews, but on the flip side, being responsive and attentive takes up too much of your time.

So, if you’re dependent on multiple platforms and a series of manual processes to manage guests, you’re probably overwhelmed, and your guest service may be inconsistent, too. This is why you need a dedicated tool to automate manual tasks, minimize the need for all those interactions, and synchronize your guest and team management.

In this review of the best guest messaging software for short-term rentals (STRs), you’ll see four different approaches to enhancing the guest experience and reducing your workload:

  1. Breezeway, which makes you highly responsive to inquiries and maintenance requests
  2. Hospitable, which uses smart messaging to recognize commonly asked questions
  3. Enso Connect, which uses AI to suggest and automate responses
  4. YourWelcome, which uses email workflows to guide guests through the check-in process

Give guests a better stay and reduce your workload
Breezeway simplifies the entire guest messaging and team management process, from check-in to check-out.

Book a Demo

1. Breezeway: Guest messaging that maximizes ops efficiency

Breezeway’s guest messaging platform “We've reduced the time we spend texting, calling, and updating by over 50%,” says Breezeway user David Wilcox of Summit Mountain Rentals. 

Breezeway is a vacation rental operations management platform with a guest messaging feature. You can purchase the messaging feature separate from its ops platform and digital guide or as a bundle with everything fully integrated. By automating tasks like scheduling, quality assurance, asset management, and reporting, the software completely streamlines STR management, which is reflected in its messaging tools. 

Firstly, the communication dashboard consolidates all your messages into one simple interface—so no hopping between tabs or apps, even when you need to jump to a conversation with a housekeeper or contractor.

Also, because Breezeway connects with your property management system (PMS), you never have to lose time manually entering reservation details—it’s all pulled directly from your PMS. Plus, when sending a welcome message or check-out reminder, you don’t need to write everything out manually—the pre-built, customizable templated messages are ready for you, and all you have to do is press send.

Breezeway message template with shortcodesBreezeway uses shortcodes to pull personalized data from your PMS into message templates.

What really sets Breezeway’s messaging solution apart is that you can receive, respond to, and resolve guest issues all within the same central portal. So, if a guest reports a broken lamp, a faulty appliance, or a leak, you can create and assign a work order directly from the message view and provide status updates until the problem’s taken care of.

Work order created within the message viewBreezeway makes responding to guest issues and communicating with in-the-field staff fast and easy.

There are other features to Breezeway messaging, too. For example, smart tech that addresses the costly issue of gap nights (or orphan nights): Breezeway identifies the gap and automatically sends a message offering guests the chance to lengthen their stay and fill that missing night in your booking calendar. 

You can also boost messaging efficiency with Breezeway's AI Suggested Replies feature, which analyzes the content of an incoming message and generates a suggested reply using AI technology. A user can then choose to send the suggested reply as-is or modify it before sending, saving your team time to compose messages.

Meanwhile, Breezeway’s digital guide fully integrates with the platform’s other solutions and provides practical information (like arrival details, WiFi passwords, and instructions) and helpful insights (like local recommendations on where to go and what to see). As well as enhancing the guest experience, this reduces the number of questions guests send you throughout their stay.

Key features


As we mentioned, you can purchase Breezeway’s messaging features as a standalone tool or as a bundled package with our ops platform and digital welcome book. For pricing details, reach out to our sales team

“With our old system, we would only know the guest's name—we would have to go back, look up the reservation, see where the guest was staying, and then switch screens again to complete the message.The consistent Google Reviews we've generated through Breezeway's texting product have been incredible for our business.” - Elaine and Lance, Seaside Vacations - See the case study

Stop the overwhelm caused by guest messages with Breezeway
The platform’s all-in-one view lets you see who the guest is and the details of their stay, and you can quickly manage maintenance issues and respond to special requests.

Book a Demo

2. Hospitable: Smart messaging

Hospitable dashboardHospitable’s smart messaging automates standard messages and responses to common questions.

Hospitable is a platform for STR automation, with direct booking website templates, channel management and task scheduling capability, and its core offering, guest messaging. The guest communication software reduces your manual tasks and increases responsiveness, which it achieves—supported by its PMS and booking platform integrations—through scheduled messaging, message templates, and smart responses.

This allows you to build multiple messaging solutions via a system of shortcodes and complex rules, which helps you respond to guests throughout the customer journey, from pre-booking to post-check-out. 

For example, if a guest sends you a commonly asked question, such as about the WiFi, the software will detect the information they need and automatically respond with the correct details. Or, if the guest has a unique question—say, about directions—you can use the platform’s ChatGPT integration to quickly formulate a response.

With Hospitable’s scheduled messages, though, you can reduce the need for those smart interactions by pre-emptively providing guests with key information, such as property access details, useful how-to’s, and review requests—much like you can with a digital guide. Also, the platform provides a unified inbox, which consolidates communication from different booking platforms.

Key features

  • Unified inbox
  • Messaging rules for automated guest communication
  • Canned responses with shortcodes
  • Scheduled messaging


Hospitable's pricing structure is flexible, with plans starting at $40 per month for two properties, and includes an initial free trial, as well as a number of Hospitable’s other STR features.

3. Enso Connect: AI automations

Enso Connect message platformEnso Connect uses AI to speed up your response time.

Enso Connect is a guest experience platform that acts as a guide throughout the guest journey, which it does by way of its branded web app, Boarding Pass. Guests access the app, where they can have their ID verified, complete check-in, see your digital guide, request extra services, and communicate with you and your team.

The guest communication software centralizes messages from email, Airbnb, SMS, and WhatsApp into a unified inbox, which you can manage by marking messages as read or unread, applying filters, and assigning conversation threads to specific team members. Also, you can send and receive messages using customized email addresses and phone numbers.

Alongside Enso Connect’s system for message management is its various AI solutions, which are powered by GPT-4. These include predicted responses as part of its approach to increasing booking inquiry conversions and improving your responsiveness. For example, if a prospective guest emails you about availability, the AI system will suggest and/or send an appropriate response.

Also, the AI integration includes ‘sentiment analysis,’ which scans guest messages to decide if they’re satisfied with their stay. Based on this, the system can automate an appropriate response, like offering a special gift or discount if the guest has experienced frustration or an otherwise negative experience.

On top of its message consolidation and AI automations, you can use Enso Connect to schedule messages, manage review requests, and collect customer data, which can be useful as part of a direct booking strategy.

Key features

  • Unified inbox
  • Scheduled messaging
  • AI-suggested responses
  • AI-automated responses


Enso Connect’s packages begin at $160 per month and include consultation, training, and support.

4. YourWelcome Advance: Email workflows

YourWelcome dashboardYou can use YourWelcome to customize email workflows to manage guests.

YourWelcome is a guest engagement tool that uses property-synced smart tablets and the platform’s software to provide short-term rental guests with a guidebook, contactless check-in, and two-way messaging. By adding the YourWelcome product Advance, you get additional check-in and messaging automation features.

Using this automated guest messaging system, you can create and customize email workflows for OTA bookings and direct reservations, with booking details pulled from your PMS. This customization includes branding your emails with logos and colors.

These workflows are essentially a way of scheduling messages to guests so you can provide them with key information at the right time based on their check-in and check-out dates. This lets you streamline the check-in process on both sides—guests can independently verify their ID and complete payment, while you get to minimize the amount of time you spend sharing information with guests or responding to their questions.

Also, you can use these communications as an opportunity to make upsells and gather customer data for your direct booking strategy and marketing efforts.

Key features

  • Customizable email workflow templates and messages
  • Advance check-in for collecting guest data and offering additional services
  • Guest verification
  • Payment processing
  • PMS and OTA integrations


YourWelcome (not including Advance) is $240 per year (volume pricing begins at 10+ units) and includes a premium 8-inch tablet, a stand and extra-long cable, and free replacement for breakage and theft. YourWelcome does not list pricing information for Advance on their website, so you’ll have to reach out to sales for a quote. 

What to look for in guest messaging software?

There’s no single answer to what functionality you need from guest messaging software, but there are usually two key concerns when it comes to building out your guest management processes: 

  • Ensuring a positive and consistent guest experience
  • Optimizing operational efficiency so guests have a fantastic stay with minimal effort and cost on the management side

And there are immediately some basic features your guest messaging solution needs to achieve this. For example, it should make it easy to inform guests about arrival, property access, and other common issues, like how to connect to WiFi. This helps guests have a smooth start to their stay and minimizes their need to message or call you with questions.

As well as pre-emptively resolving common questions, your messaging system should make it easy to handle questions that aren’t so easy to predict. For example, if there’s a maintenance issue, you need an easy way to respond to the guest, reach out to your staff, and then track task status in real-time.

Also, you need to manage guest messages within a single dashboard review, where you can see chat history, utilize message templates, and access essential guest data.

Here’s a look at some of the most valuable features in a comprehensive STR guest messaging platform:

  • PMS and OTA integrations
  • A central portal with two-way messaging
  • Auto-filled message templates
  • Integrated work order creation and assignment
  • Integrated task tracking
  • Bulk messaging
  • Additional revenue solutions
  • Digital guide or scheduled messaging

Guest messaging for 5-star ratings & business performance

The guest experience is at the heart of the STR industry, which requires you to accommodate guest needs and meet their expectations in a way that’s sustainable within the scope of your business operations. To make this possible, you need a messaging solution that minimizes your manual tasks while upholding your quality of service.

You can achieve this with software that aligns your guest management and team operations processes.

With Breezeway’s user-friendly solution, you can:

  • Pull guest data from your PMS
  • Access pre-set templates to quickly provide guests with the information they need
  • Easily create and assign tasks in response to guest requests and issues
  • Schedule messages for arrival and departure days
  • Drive revenue with automated gap-night messaging
  • Do all this within a central messaging portal

    Give guests a better stay and reduce your workload
    Breezeway simplifies the entire guest messaging and team management process, from check-in to check-out.

    Book a Demo