The Best AI Autoresponders for Airbnb & STR Hosts (Without Hiring Help)

Discover the best AI autoresponders to automate Airbnb guest messaging, save time, and scale your STR portfolio—without hiring help

Friday Night Scaries?

Forget the Sunday scaries—the sense of dread as the weekend wraps up. Short-term rental (STR) hosts growing a portfolio have the Friday Night Scaries: five check-ins, two no-reply texts, one guest locked out because they “swear the door code isn’t working,” and someone else asking—again—what the Wi-Fi password is.

You check your messages and think: “Didn’t I already send that?” You did. Twice. And it's printed and framed in the living room.

This is the unglamorous reality of managing guest messaging at scale. Scaling your short-term rental business sounds exciting—until you realize that more properties mean more guests, more questions, and more hours glued to your phone.

Recently, I worked with a client at a tipping point: expanding units, maximizing occupancy, and prepping to hire staff. Instead, we explored a smarter, leaner solution: AI guest autoresponders for short-term rentals.

This post breaks down everything we learned—what works, what to ask vendors, and why AI autoresponders might just be your most impactful digital hire.

Why STR Guest Messaging Needs to Change

If you’re scaling from 1 to 10+ units, you might not even realize how much time you're spending on repetitive guest messaging. Or, like many of my clients - you do know, but you don’t believe a “bot” can solve that issue for you and still deliver. I’m here to challenge you on that belief; you can give great service by systematizing your business, giving prompt responses, and jumping in only when your touch is needed versus the hamster wheel of constant interruptions.

The truth is, when you’re answering the same five guest questions over and over, that’s not “great service”—it’s an operational red flag.

AI Guest Messaging Tools can solve;

Time drains from repeat inquiries: Wi-Fi, check-in times, parking, trash pickup—your time is valuable, and answering these 20 times a week is not a good use of it.
Burnout and snark fatigue: We all try to stay polite, but by the fifth Friday night message asking the same thing, interrupting dinner or time with friends - it’s easy to slip into passive-aggressive replies. That’s not the host brand most of us want to build.
Risk of poor reviews: A missed or delayed response might feel minor in the moment, but it can easily tank your review scores.
No insight into patterns: Without systematizing communications, you don’t see what questions are being asked the most—and that means we don’t know where the opportunities exist for improving.

Most importantly, when our brain is overloaded handling small issues, we are not able to focus on the higher-level tasks that actually grow revenue—like pricing strategy, marketing, or adding new properties.

Autoresponders—especially AI-powered ones—help offload the noise so you can tune in to what matters.

Prevention is the Cure: Smarter STR Communications

Before we even get into autoresponder platforms, let’s talk about prevention. One of the smartest moves to make as a host is to reduce the need for guests to message in the first place. AI is a powerful tool, but it’s most effective when paired with a great communications campaign to start with. Here are some ideas:

✅ Digital Guest Guides

Ideally, a guest guide should be more than a PDF attachment. Modern digital guidebooks (like Touchstay) can include dynamic content, images, videos, maps, and links—all accessible from a QR code in the home, an email link in advance. If a guest doesn’t know how to use the fancy espresso machine, a two-minute video in the guidebook can eliminate five messages (and the frustration of feeling “stupid” on their end).

✅ QR Codes for Key Instructions

QR codes next to the thermostat, hot tub, or built-in coffee machine can deliver micro-content right when and where the guest needs it. This is communication on their terms—not buried in a pre-arrival message or lost in their inbox.

✅ Layered Communication, Not Long Paragraphs

Have you struggled with knowing you sent guest info - and they are messaging you asking questions you know you sent? Instead of sending one big wall of text at check-in, consider drip messages based on timing and trigger points. For example:

1 hour before arrival: "Hey! If you’ll be checking in after dark, here’s a quick video walkthrough of the entry."
30 minutes after check-in: “Here’s the digital guide again—most guests find the local eats section super helpful after a long travel day.”

Delivering the right message at the right time increases the chance it’s actually seen—and reduces the need for repeat questions. You can pre-schedule these messages to go out on auto-pilot; the biggest downside is that they go out on auto-pilot even if you’ve just responded to a question from the guest unless your communication system is set up to avoid this.

And when questions do come up? That’s when your autoresponder earns its keep.

❌Not All AI Responders Are Created Equal

Let’s be real—there’s a flood of tools on the market, and not all “AI” is created equal. Some are auto-messaging tools disguised as AI. Others are true generative AI systems capable of mimicking human conversation, learning, and responding in context. Here’s a snapshot of four different versions currently available (keep in mind, this list in not exhaustive by any means, just a sample - and these companies are all changing capabilities quickly, so be sure to do your own due diligence!)

🔹 Guesty

What it is: Part of a full property management software (PMS), it offers rules-based automations like auto-send for check-in/check-out info, but not truly AI.
Good for: Hosts already using Guesty who want a built-in solution for timing-based communication.
Limitations: Doesn’t generate responses based on guest questions. No true AI learning or guest intent prediction.

🔹 HostAI

What it is: A fully generative AI solution that acts like a 24/7 co-host, anticipating guest needs and customizing responses.
Key features:
- Learns your communication style
- Escalates complex messages appropriately
- Can be set to feel like “you” or clearly as an autoresponder
Standout: Upsell triggers based on guest behavior and context. A solid fit for hosts who want scale and personalization.
Potential drawback: This is a pricey solution for smaller operators. It also doesn’t initiate any communications, just responds

🔹 GuestLabs

What it is: A chatbot-style AI focused on responsiveness, tone, and brand integrity.
Key features:
- Responds in guest’s language
- Keeps consistent brand voice
- Escalates and flags emergencies
Standout: Integrates with Google Maps and Yelp to enhance local recommendations. Great for guest-facing polish.
Watch out for: Some reviewers suggested the AI-generated responses were still not as tone-aware as they’d like

🔹 Besty AI

What it is: A newer player that combines guest communication and operational AI.
Key features:
- Real-time sentiment analysis
- Can assign tasks from guest messages (like dispatching a cleaner or maintenance tech)
Best for: Hosts with lean teams who want messaging + operations support.
Limitation: Still maturing in terms of platform integrations.

The Inside Scoop

In my quest to find the right solution for my client, the process of doing sales demos with various vendors was helpful. But when I did a free trial of one guest autoresponder in my own portfolio a whole slew of more insights and questions came up. So I’m going to try to distill this down, so you don’t have to.

✅ Percentage of Questions Handled Autonomously

Always ask: What percentage of guest messages can your AI handle without escalation?
Some tools might handle 50-70% of messages, others less or more—knowing this helps you plan for staffing backup or escalation workflows. Tip: not every product is an auto-reponder; some are generative while requiring someone to hit “send”.

✅ Escalation Logic

A great AI should know its limits. If a guest says, “I hear water leaking in the basement,” the tool should not respond with “Enjoy your stay!”
Look for tools that detect emergencies, flag priority issues, and escalate to you or your team automatically.

✅ Tone & Branding Controls

Can you train the AI to sound like you? Whether your brand voice is warm and witty or short and to the point, consistency matters. But here’s the other side - you don’t have to have it sound like you. When I set up a property using Hostbuddy AI, I picked if I wanted it to emulate me, to be part of a team, to disclose upfront that it was AI or if it would respond affirmatively if asked if it was AI.

✅ Communication Channels Covered

Does it cover:
- Platform inboxes (Airbnb, Vrbo)?
- SMS or WhatsApp?
- Email?
Email integration is the wildcard—some tools skip this entirely, so if that’s part of your guest communication flow, verify compatibility. There are workarounds, but it may take a bit extra. You also need to ensure it integrates with your specific channel manager or PM.

✅ Works With or Without a Channel Manager/PMS

Most AI tools require integration with your PMS (like Hostfully, Guesty, OwnerRez, Hospitable).
If you’re not yet using one, you may need to add that step—or look for a solution that can operate independently (though those are rare).

✅ Response Type: Auto or Assist

Some tools generate suggested replies for you to send (human-in-the-loop).
Others send messages automatically unless they hit an escalation trigger.
Choose based on your comfort level—many hosts start with assist mode, then switch to full auto once they trust the system.

Guest Chatbots in Real-life for Short-Term Rentals

Let’s ground this in reality.

Maybe you are a solo operator managing 10 STR units—and burning out. Answering every guest question yourself. No VA, no co-host, just grit and caffeine. I’ve worked with more than one of these operators - brilliant go-getters buried in responding to guests instead of growing their business.

Here’s the strategy:

Audit your communications; what questions are you getting on repeat?
Get proactive;
- Add QR codes linking to short video tutorials (entry door, fireplace, coffee machine)
- Switched to a digital guidebook with timed reminders via SMS
Try an AI autoresponder

A true autorespond should decrease your need to respond to guest communications dramatically.

What to Watch Out For

The AI space is moving fast—sometimes faster than the tools themselves. While the potential is huge, here are a few things to be cautious about before diving in:

⚠️ “AI-Washed” Products

Just because a tool markets itself as AI doesn’t mean it truly is. If it only sends pre-written messages on a timer, that’s automation—not intelligence. Ask how the AI is trained, what it learns, and what input it requires from you.

⚠️ Vendor Lock-In

Some platforms make it hard to export data or switch tools later. If your entire guest communication strategy depends on one system, make sure it has a path to grow with you—or an exit ramp if needed.

⚠️ Over-Automation

It’s tempting to automate everything, but some messages deserve a human touch. A guest asking about nearby vegan restaurants on their anniversary trip? That’s a moment to shine, not script.

⚠️ Data Privacy

These tools access guest data. Be sure to confirm how your guests’ personal information is handled, stored, and protected. You’re not just outsourcing messaging—you’re entrusting a key part of your guest experience.

My Quick-Start Recommendations

Here’s how to begin, whether you’ve got 3 properties or 30:

🛠 Step 1: Audit Your Communications

Look at your last 20–30 guest messages. What are the top 3–5 repeat questions? These are your autoresponder’s first training inputs.

🧠 Step 2: Define Your Tone

How do you want to sound? Warm and casual? Concise and efficient? Outline this once, and reuse it when configuring or training your AI.

🧾 Step 3: Set Up Your Digital Foundation

Use a digital guidebook with clickable sections (not a static PDF)
Add QR codes for complex amenities (video > text when possible)
Create timing triggers for key info (arrival, post-check-in, pre-checkout)

🤖 Step 4: Choose a Tool That Fits

Already using a PMS or channel manager? Start there—Guesty, Hostfully, OwnerRez, etc. may offer integrated tools or partner apps.
New to tech? Try a standalone option like HostAI or GuestLabs with strong onboarding support.
Want operations support too? Explore Breezeway’s option - while its not an autoresponder, its operational ecosystem is robust and minimizes the need for an unwieldy tech stack.

🧪 Step 5: Start in “Assist” Mode

Let the AI draft responses that you approve before going fully auto. Once you’re confident, flip the switch. You’ll never look back.

Tech as a Bridge, Not a Barrier

AI isn’t about replacing hospitality. It’s about removing the friction—so you can show up when it really matters and not burn out in the process. Airbnb hosts and STR operators are using AI in many ways, but AI to interface with rote guest communications is a smart step for a growing STR business.

Autoresponders are like giving your best customer service day… every day… at 2am… without needing more staff. For STR operators with lean teams and growing portfolios, it’s one of the highest-leverage tools you can implement.

Whether you’re just exploring tools or ready to offload your inbox entirely, the right system can help you run a tighter ship, deliver better guest experiences, and finally reclaim your time.

Let’s Talk

If you’re in the process of scaling, evaluating tech tools, or just sick of answering “what’s the Wi-Fi?”—I’d love to help.

I work 1:1 with STR owners and operators to build scalable systems that actually fit your business (and your budget). Let’s figure out if AI autoresponders make sense for you—and which one will serve you best.

👉 [Book a consult] or just [reach out to chat]—I’d love to hear where you’re at and what you’re building.

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Hey Boss! I'm Kate, owner/founder of The CEO Host. If you are interested in taking a leap into short-term rentals - or have some questions about your existing business, my goal - passion, and career, is to help YOU succeed. I've coached hundreds of folks getting started or looking to optimize, analyzed more deals (and duds) than I could count, completed thousands of hours of education and training, attended conferences... So don't be shy. A good CEO knows to bring in expert help - and that's what I'm here for! Lets HOP ON A CALL and chat!

Categories: : Self Managing & Operations