100 Vacation Rental Guest Touchpoints Improved with AI

AI is poised to transform the guest journey. We predict these 100 touchpoints will be improved with emerging multi-modal models.
Updated: 1/18/2024
The possibilities of AI seem endless — and if you're new to implementing this technology in your vacation rental business, it can be hard to know where to start.

So we developed a list of 100 guest touchpoints that have the potential to be improved with AI over the next few years, from better property descriptions to virtual check-in tours to timely "don't forget your cell phone charger" reminders. Read on to get your wheels turning and envision all the ways our AI-enabled future can save your team valuable time while providing a more personalized experience to your guests.


Search and Pre-Booking

AI is going to simplify how guests find and prepare for their stay. With AI, guests can look forward to more accurate property photos, descriptive listings that feel personal, and an overall smoother booking experience that anticipates their needs and preferences.

1. Viewing Rental Photos

Guest decisions hinge on property photos, making their quality and appeal essential.

Soon, cutting-edge multi-modal models will assist not only in augmenting the visual allure of your property photos but will also intelligently detect and caption nuanced features, ensuring your amenities are accurately highlighted to inform and captivate the right travelers.

2. Reading Property Descriptions

Crafting text that conveys a property's charm and features can be tough, and unclear descriptions can lead to misunderstandings and poor reviews.

Multi-modal AI from products like AutoMate will simplify this step by generating vibrant, tailored descriptions for each listing, ensuring guests' expectations are met.

3. Visiting Your Website

Showing the right property to the right guest at the right time is the key to future conversions on your website.

AI will soon optimize property visibility by dynamically tailoring listings and search results to guest preferences, significantly increasing the likelihood a unit books.

4. Checking Availability

Guests encounter frustration with discrepancies between available dates shown and actual availability, leading to a less-than-seamless booking experience.

Predictive AI can offer real-time alternative date suggestions tailored to guests' scheduling needs, streamlining the booking process and enhancing guest satisfaction.

5. Evaluating Guest Reviews

Guest reviews can sway decision-making, with negative feedback sometimes outweighing the positive - regardless of issue resolution.

AI models can analyze trends in reviews to guide enhancements and provide personalized review responses, including targeted offers to past guests.
6. Inquiring About the Property

Property managers juggle numerous inquiries - risking delayed and impersonal responses - while language differences may lead to misunderstandings.

Soon, multi-modal AI chatbots will deliver real-time, round-the-clock, and multilingual engagement for routine questions, tailoring conversations to guest preferences and utilizing visual and interactive aids to eliminate ambiguities.

7. Receiving Host Responses

Responding to guest inquiries demands a delicate balance between timely personalization and efficiency, all while maintaining the accuracy of the information being shared.

AI will help in crafting instant responses that are both personal and aware of the guests' unique needs, while simultaneously sorting inquiries by urgency, enabling property managers to address the most pressing questions first.

8. Understanding Pricing and Fees

Guests often grapple with complex pricing structures and unexpected fees, which can reduce transparency and erode trust.

Future AI pricing tools can offer clarity by reflecting live market trends and transparently communicating cost determinants, providing confidence and creating loyalty among guests.

9. Reading Cancellation Policies

Guests often struggle with the intricacies of cancellation policies, and providing individual explanations is a significant time investment.

AI will simplify policy communication, using tailored interactions to clarify terms and preemptively address potential booking concerns.

10. Knowing House Rules

Ensuring guests are aware of rental policies such as pet or smoking rules can be challenging, often resulting in unintentional rule breaches.

AI-driven multilingual support aims to dissolve language barriers, helping deliver clear policy explanations and reducing misunderstandings.

11. Finding Special Offers

Guests seek out special deals while managers encounter challenges in personalizing and managing these offers effectively.

AI will streamline personalization, targeting offers by analyzing guest data and predicting prime opportunities, reducing manager workload and boosting profitability.

12. Comparing Properties

In a sea of choices, property managers grapple with differentiating their offerings as guests sift through dozens of listings.

Future AI tools will dynamically accentuate a property's standout qualities, tailoring the listing highlights to align with guest preferences during the comparison process.

13. Using FAQ Resources

Property managers struggle to predict and compile a comprehensive FAQ list that meets all guest inquiries, and keeping it up-to-date demands ongoing effort.

In the future, AI will dynamically expand FAQs by learning from guest interactions and parsing listing websites, while AI chatbots will provide immediate, accurate answers to guests 24/7.

14. Booking Add-Ons

Managers often struggle to handle add-on offerings due to limited resources and lack of insight into guest preferences.

AI will automate inventory and tailor suggestions that enhance the guest experience and boost manager profits.

15. Selecting Stay Dates

Guests often face a cumbersome process when their preferred stay dates are unavailable, and finding alternative dates or options can lead to frustration and potential booking loss.

When a guest finds their desired dates taken, AI will seamlessly suggest the best alternative dates or similar available properties within your portfolio, enhancing the booking experience and reducing the chance of guests seeking accommodations elsewhere.

16. Submitting Guest Information

Collecting guest details often entails a tedious and repetitive booking process, compounded by the critical need to maintain data privacy and security.

AI will simplify bookings with auto-filled forms based on learned behaviors, easing the burden for guests during the checkout process.

17. Choosing Additional Services

Property managers often struggle to highlight the most pertinent add-on services, missing opportunities for effective upselling.

AI will help tailor extra service offerings by analyzing guests' booking profiles and historical preferences, enabling personalized upselling that resonates with each individual traveler.

18. Applying Discounts

Advanced AI systems will streamline promo code tracking, offering actionable insights for strategic refinement, and personalize discount distribution, elevating the effectiveness of special deals and guest engagement.

26. Reviewing Prices

Advanced algorithms analyze listings, competitors, travel patterns, local happenings, and booking history to recommend pricing strategies that raise RevPAR.


Imagine the ease of managing guests before they even set foot on your property. AI is here to upgrade your pre-arrival protocols, making every interaction feel tailor-made. You’ll be able to send out welcome messages that resonate with individual guests, provide clear, custom check-in guidance, and curate local experience tips. This means fewer questions and smoother starts for every new arrival.

27. Welcome Messages

Generic communications can lead to guests feeling like just another number, diminishing the personal touch of their travel experience.

Leveraging AI will tailor welcome messages for a warmer, personalized touch, reflecting guests' unique preferences and ensuring they feel valued and excited about their upcoming stay.

28. Custom Check-In Instructions

Use AI to streamline check-ins with personalized, property-specific instructions tailored to each guest's needs and preferences.

29. Special Guest Requests

Future AI-integrated platforms will effortlessly track special requests, alerting team members proactively to guarantee every detail is addressed for an impeccable guest experience.

30. Pre-Arrival Guides

Crafting a detailed manual for each rental property is a labor-intensive task, compounded by the need for regular updates to keep the information current.

AI will pave the way for the creation of interactive, dynamic digital guides that provide real-time updates and seamless accessibility across various devices, complete with virtual property walkthroughs that heighten both guest anticipation and satisfaction.

31. Pet Needs

AI will craft directions for pet-friendly spaces, amenities, and local pet services for guests traveling with animals.

32. Recommendations for Local Dining, Shopping, and Activities

In the future, an AI engine will meticulously tailor recommendations for guests, factoring in unique preferences and behaviors, along with the latest local trends, ensuring property managers offer always-updated, bespoke local guides with ease.

33. Tailored Local Experiences and Concierge Services

Customizing suggestions to align with individual guest's tastes poses a significant time investment and scalability challenge across a portfolio of vacation rentals.

Envision an AI-powered virtual concierge that not only converses with guests about local attractions but also seamlessly handles reservations and itinerary planning, all personalized to guest preferences.

34. Parking and Transportation

Customizing advice to fit a guest's unique requirements, from family-friendly transit to secure parking, demands significant attention to detail.

AI will anticipate and address guest transportation needs with precision, suggesting options like family-appropriate transit solutions, secure parking arrangements, and even facilitating car rental or shuttle bookings directly through tailored recommendations.

35. Reminders

Managing the delicate balance of timely reminders without overwhelming guests is pivotal for an optimal pre-stay communication strategy.

AI will help pinpoint the perfect timing for reminders, ensuring guests receive pertinent information exactly when they need it, enhancing the overall guest experience.

36. Pre-Arrival Grocery

Some guests prefer to have the rental stocked with groceries or specific amenities before arrival.

AI could organize pre-arrival shopping for guests, based on predictive analysis of their preferences, and manage orders and deliveries seamlessly.

37. Necessary Travel Documentation

Based on the guest's origin and destination, AI can remind guests of any necessary travel documentation, such as visas or vaccination certificates.

38. Unveiling Hidden or Unique Features

AI can help craft instructions or hints for discovering any non-obvious, unique features of the property that could enhance the guest experience.

39. Weather Forecasts and Preparation Tips

Preparing guests for local weather conditions is crucial for their comfort.

AI could soon provide personalized weather forecasts and preparation tips, helping guests pack appropriately and plan their activities accordingly.

Arrival & Check-In

Say goodbye to one-size-fits-all instructions and impersonal greetings. With AI, property managers can offer guests tailored route planning, proactive guidance, personalized walk-throughs, and intelligent issue resolution.

40. Locating the Property

Crafting universally clear directions is tough, as guests' travel savvy and local knowledge vary widely.

In the future, AI integration will personalize route planning to the rental, balancing scenic appeal with efficiency and adapting in real-time to traffic and weather updates, all tailored to guest preferences.

41. Using the Lockbox or Digital Lock

Guests often face access issues due to technical glitches or electronic lock battery failures, demanding urgent intervention from the manager.

AI systems will proactively monitor digital lock performance, predict and rectify potential faults, and automatically initiate maintenance actions, ensuring seamless access for guests at all times.

42. Entering the Rental for the First Time

The initial step into a rental is pivotal; guests expect perfection, a standard that's challenging to maintain, especially with back-to-back bookings.

In the future, AI will streamline first impressions with virtual check-in experiences, offering an interactive digital walkthrough that points out vital amenities and answers questions as guests settle in.

43. Initial Walk-Through Inspection and Reporting Issues

Finding the sweet spot where guests feel compelled to report issues upon arrival without the process feeling burdensome.

An AI-driven app will engage guests in a streamlined, interactive inspection upon arrival, reframing reporting as an engaging element of their stay rather than a chore.

44. Reading Welcome Materials and Guestbook

Delving into guestbooks or welcome materials can be a generic encounter, sometimes lacking in personalization due to time constraints on hosts.

Imagine a future where an AI virtual assistant tailors welcome materials to each guest, offering an interactive, language-appropriate greeting with on-demand answers to enhance their stay.

45. Connecting to the Wi-Fi

Seamless internet access is crucial, yet guests often face obstacles with complex or bad Wi-Fi instructions.

In the future, AI will streamline this process to provide guests with intuitive, device-tailored instructions and visuals for hassle-free Wi-Fi access.

46. Reading Emergency Procedures

AI can help inform guests about emergency exits, safety kits, and procedures in case of fire or other emergencies.

47. Bike or Equipment Rental Info

AI can craft info and reservation details for bikes, scooters, or sports equipment available at or near the property.

48. Unpacking Belongings

Guests often face frustration due to vague directions for locating storage spaces or operating security devices like alarms and safes.

Future AI will anticipate guest storage preferences offering interactive, AI-powered tutorials on storing and securing possessions as well as operating device-specific security systems.

49. Property Maps

Finding one's way around a large rental property or complex can be daunting for guests.

AI-generated interactive property maps could guide guests to different areas or amenities of the rental using their mobile devices.

50. Smart Energy Management System Introduction

Future AI can introduce guests to smart energy systems, personalize settings to guest preferences, and explain how they contribute to sustainability efforts.

51. Personal Assistant

An AI personal assistant could help guests with various requests during their stay.

Upon arrival, guests could be introduced to an AI assistant that can help with everything from controlling smart devices to answering local questions.

52. Welcome Gifts

Using AI, property managers can curate and manage inventory for personalized welcome gifts, considering guest preferences and past feedback.

53. Pre-Arrival Packages

Curated pre-arrival packages are offered based on AI analysis of guest preferences, which could include local delicacies, in-room amenities, or themed decorations for special occasions.

54. Reviewing Safety Features

Future multi-modal AI systems will offer interactive guidance on safety features, using various methods like voice, video, or even augmented reality to confirm understanding, all tailored to the guest's language and unique requirements.

During the Stay

With AI shaping the future of property management, your guests are in for a smoother stay, from adjusting the thermostat to troubleshooting appliances. For you, it means less guesswork, fewer calls, and happier guests.

55. Adjusting the Heating/Cooling System

In the future, AI will intuitively calibrate the perfect arrival temperature based on guest preferences and provide clear, unit-specific instructions. Voice-activated adjustments and app-based controls will streamline the experience, while AI oversight maintains energy efficiency and instantaneously notifies managers of system issues.

56. Using Kitchen Appliances and Finding Cookware/Utensils

Guests may struggle with unfamiliar appliances, risking damage, while locating the right cookware and utensils can become a time-consuming scavenger hunt.

Future AI-powered solutions will offer virtual guides to seamlessly demonstrate appliance usage and direct guests to kitchen items.

57. Requesting Additional Items or Restocking from the Host

Pinpointing the perfect timing for item replenishment while respecting guest privacy remains a tricky balance for hosts.

Future AI solutions will predict and notify guests about restocking, while providing managers with data-driven insights for maintaining ideal supply levels, tailored to each stay.

58. Using Entertainment Options

Imagine a future where AI tailors entertainment to each guest's taste, drawing from their profiles and past likes.

AI-enabled platforms will offer interactive, simple-to-follow guides and personalized suggestions for movies, shows, and games, promising a seamless and delightful stay for every guest.

59. Interacting with Smart Home Devices

Guests sometimes struggle with smart home devices due to a lack of tech familiarity or knowledge of a particular brand's ecosystem, while managers grapple with remotely educating guests on their usage.

AI advancements will simplify smart home interactions for guests, as virtual assistants adapt to various languages and understand personalized commands.

60. Sleeping in Beds and Using Linens

Guests' comfort with bedding is hit-or-miss, challenging managers with diverse linen inventories and quality upkeep.

In the future, AI will guide managers on ideal arrangements, while smartly managing linen inventory and predicting replacement times for top-notch comfort.

61. Using the Laundry Facilities

Guests sometimes need help with unfamiliar washers and dryers, while managers occasionally overlook stocking essentials and providing clear instructions.

AI will transform laundry use into an intuitive experience, offering multilingual guidance and smart notifications for supply replenishment tailored to guest stays.

62. Interactive Local Storytelling and History

AI-driven interactive storytelling could add depth to guests’ experiences by sharing local tales, historical facts, and cultural customs.

63. Experiencing Plumbing Issues

Guests often delay reporting minor plumbing issues, risking escalation into major concerns.

Multi-modal AI will streamline the reporting process, enabling guests to promptly and effortlessly communicate plumbing concerns via voice, text, video, and images - ensuring swift resolution.

64. Notifying the Host of Maintenance Issues

Property managers juggle monitoring multiple communication platforms for maintenance issues, which increases the risk of missing a crucial issue.

Multi-modal AI chatbots will converge communications across apps, prioritizing messages for managers and offering guests real-time acknowledgment of issues and scheduling resolutions.

65. Contacting the Host for Local Advice or Assistance

In the future, multi-modal AI will be the cornerstone of providing personalized, always-current local guides. AI can deliver custom recommendations matched to guests' tastes and real-time happenings.

66. Receiving Mid-Stay Communications from the Host

Personalizing mid-stay communications is a time-intensive task that strives to balance attentiveness with guest privacy, ensuring an uninterrupted, positive experience.

In the future, AI will intuitively automate personalized guest communications, considering preferences and behaviors to deliver seamless, considerate interactions that enrich the guest's stay without requiring constant manual oversight.

67. Maintaining the Property (Trash Disposal, Cleaning Up Spills)

Multi-modal AI will offer proactive and courteous guidance to guests, reinforcing maintenance rules through timely reminders for trash disposal and checkout procedures without intruding on their stay.

68. Custom Room Condition Settings

AI could learn these preferences and automatically adjust room conditions to suit each guest, enhancing comfort without guest intervention.

69. In-Stay Feedback Collection

Collecting feedback during the stay allows immediate action on any issues.

AI can solicit and compile real-time feedback, ensuring guests are satisfied throughout their stay.

70. Housekeeping Schedules

Based on guest itineraries or in-property sensor data, AI can optimize housekeeping schedules to minimize guest disruptions.

71. Late Check-Out Requests

An AI system manages late check-out requests based on availability and guest status, automating approvals or suggesting alternative options.

72. Suggesting Offset for Carbon Footprint

If the guest is environmentally conscious, AI could calculate the carbon footprint of their stay and suggest ways to offset it, including participating in local green initiatives.

73. Shopping Assistant

Provides guests with AI-curated shopping lists for local markets, tailored to cooking preferences and dietary needs, including directions and local recommendations.

74. Interacting with Guest Service Agents

AI advancements will empower your service teams to respond with greater speed and accuracy, ensuring your guests receive top-tier support that enhances their overall experience.

Check-Out & Departure

AI is about to make checkouts a breeze. As a property manager, you'll see fewer hiccups when guests leave, thanks to AI reminders keeping guests on track with tasks like stripping beds, taking out trash, and not forgetting their belongings.

75. Receiving Check-Out Instructions

In the future, multi-modal AI technology will interactively lead guests through a personalized check-out process, delivering tailored instructions through their favored communication modes for a more seamless transition between stays.

76. Stripping Beds / Gathering Linens if Requested

Guests often forget or misunderstand the request to strip beds and gather linens, if needed upon departure.

In the future, multi-modal AI will proactively send customized departure reminders, complete with property-specific video clips or animations, guiding guests through the check-out process and ensuring a seamless transition for every stay.

77. Doing a Final Sweep for Personal Belongings

Guests may overlook personal items on their way out, creating a potential hassle for themselves, extra work for property managers, and a logistical puzzle for item returns.

With multi-modal AI, guests could receive prompts from a virtual checklist to secure their belongings before departure, while AI could streamline the communication process for returning forgotten items.

78. Taking Out the Trash or Recycling

Guests often struggle with local trash and recycling regulations, and ensuring compliance with property waste policies demands comprehensive yet user-friendly communication.

AI can offer intuitive visual sorting guides tailored to local regulations, coupled with timely, clear notifications about trash pickup schedules and guidelines, effortlessly steering guests toward the correct practices with unobtrusive reminders.

79. Notifying the Host of Departure

In the future, managers will use AI-powered check-out alerts and a centralized dashboard to monitor departures across multiple properties, streamlining their operations.

80. Returning Keys to a Lockbox or Designated Area

Misplaced keys by guests can create security risks and require time-consuming coordination for retrieval.

Future integration of AI will offer personalized, automated reminders to ensure keys are returned to their designated spots, streamlining the process for both guests and property managers.

81. Cleaning Services

Ensuring a vacation rental is cleaned promptly after check-out is crucial for incoming guests.

AI will optimize cleaning schedules based on actual check-out times and specific cleaning needs highlighted by guest feedback.

82. Journey Home Traffic and Weather Updates

AI can provide up-to-date traffic and weather information for a safe and efficient return home.

Post-Stay Engagement

AI tools will make following up with guests a breeze. They'll help you send out personalized thanks, nudge for reviews, parse survey data, and offer smart incentives, all without swamping your team's to-do list.

83. Receiving a Thank-You Message from the Host

Personalized post-stay communication remains pivotal but can be burdensome due to the time needed and the potential for human error.

Looking ahead, AI will craft individualized thank-you notes, informed by guest data and stay specifics, ensuring heartfelt responses without the hassle.

84. Being Invited to Leave a Review

AI platforms will seamlessly prompt guests for post-stay reviews using tailored messages, while AI-enhanced analytics ensure no guest is overlooked or asked too many times.

85. Submitting a Review of the Property and Experience

Navigating review submissions can be complex for guests, and managing responses is time-consuming for property managers.

AI will offer streamlined, intuitive interfaces and instructions to help guests leave reviews on the right platforms.

86. Engaging with a Review Response from the Host

Responding promptly and thoughtfully to every review demands significant effort, especially when tactfully addressing negative feedback while maintaining a balance between professionalism and personal touch.

AI will provide personalized review responses, skillfully managing criticism and celebrating positives to resonate with both reviewers and future guests.

87. Receiving a Follow-Up Survey or Feedback Request

AI will play a pivotal role in personalizing and optimizing survey delivery, pinpointing the perfect moment for interaction. Intelligent data analysis will effortlessly distill valuable insights from feedback, streamlining the process for property managers and enhancing the overall vacation rental experience for guests.

88. Being Offered a Discount or Incentive for Future Stays

AI tools will enable predictive offer systems that discern guests' likelihood to rebook and personalize incentives based on individual booking histories, fostering loyalty and repeat visits.

89. Sharing Experiences with Friends or on Social Media

AI will streamline guest incentivization to share experiences, offering sophisticated tracking for pivotal marketing insights and robust online reputation management.

90. Receiving Marketing Communications for Repeat Visits

In the future, AI will strategically tailor marketing efforts by analyzing individual guest data and crafting bespoke messages that engage rather than overwhelm, hitting the sweet spot of timing and frequency.

91. Photo Album Creation

Multi-modal AI could create digital memory albums for guests from pictures and activities logged during their stay, incentivizing sharing and fostering nostalgia.

92. Check-In for Return Visits

Returning guests appreciate faster, personalized check-ins. AI can remember guest preferences from previous stays and streamline the check-in process for future visits.

93. Re-Experiencing a Stay in VR

In the future, guests could use AI-driven virtual reality tours to relive moments from their stay providing an immersive memory that prompts return visits.

94. Satisfaction Scoring

AI can analyze detailed feedback and create satisfaction scores that evolve over time, giving precise insights into the guest experience.

95. Property Upgrades and Recommendations

AI can aggregate guest suggestions to inform property managers about desired upgrades or added amenities.

96. Pricing Feedback

Dynamic pricing can sometimes surprise guests post-stay if they find rates have changed.

AI can gather feedback on guests' experiences with pricing and inform more sensitive dynamic pricing models so that guests don’t feel ripped off.

97. Issue Resolution

AI can predict possible recurring issues based on past feedback and preemptively suggest solutions or maintenance checks.

98. Next-Stay Discounts

AI can tailor discount offers for the next stay based on guest behavior and price sensitivity, maximizing the likelihood of a return booking.

99. Custom Event Invitations for Past Guests

AI can keep track of local events and match them with past guests' interests, sending out custom invitations that might interest them for future stays.

100. Viewing Content

Keeping guests informed and engaged through content marketing can drive repeat business and attract new customers.

Leveraging AI, property managers will more easily craft captivating blog posts, social media content, and newsletters that highlight their properties and local attractions, fostering lasting connections and increasing referrals and rebookings.

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