Guest Messaging: Virtual Assistants vs AI

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Guest Messaging: Virtual Assistants vs AI

Alex Shelley
Member since 2020 · 2 posts · 0 votes

Hi Everyone. My portfolio has grown to the point that myself and team should no longer be doing all of the guest messaging and we need to outsource. How do those of you with bigger STR portfolios manage guest communications? My questions is do I use AI to filter all the easy questions or just use a VA? or Both? Any insight, software recommendations, or recs on where to find a great VA would be greatly appreciated.

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Andrew Street
Member since 2019 · 1k+ posts · 292 votes
1y

We use a mix of both. AI handles the common/quick questions through our PMS, and a VA manages anything that needs a personal touch.

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  • Collin HaysBusiness Member
    Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
    1y

    Nothing more frustrating for guests than trying to get help from someone in East Asia. On the other hand, If you do that, that might take care of your growth problem. 

    [email protected]806-672-7102
    SMOKY MOUNTAIN FALLS INC.51 Review
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  • Jeremy Jareckyj
    Real Estate Agent · Salt Lake City, UT · Member since 2020 · 490 posts · 205 votes
    1y
    Quote from @Alex Shelley:

    Hi Everyone. My portfolio has grown to the point that myself and team should no longer be doing all of the guest messaging and we need to outsource. How do those of you with bigger STR portfolios manage guest communications? My questions is do I use AI to filter all the easy questions or just use a VA? or Both? Any insight, software recommendations, or recs on where to find a great VA would be greatly appreciated.


    VAs can help a lot BUT the problem is finding the right VAs... i would say only 10-20% can operate effectively and even then there is a learning curve to exactly how you operate . I think more AI will become an option soon, especially with the PMS softwares. Right now a lot of the PMS softwares have a very basic AI but I know many plan to implement a better one soon in the coming year. Maybe having just one VA to handle basic communication will help you for now. during certain parts of the day

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  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    1y

    I second Jeremy above. I have Filipino VA's that cover our night shift - but we went through a lot over the years to settle on who we have today. They work for me only and its been about 4 years. Punctual and great English with minimal accent.

    [email protected]813-563-0877
    Vacation Rentals of Florida53 Reviews
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  • Alex Shelley
    OP
    Member since 2020 · 2 posts · 0 votes
    1y

    where did ya'll find your VAs? Any suggestions and tips to help get them ramped quicker or avoid major mistakes?

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  • Martin D.
    Realtor · Sedona, AZ · Member since 2020 · 70 posts · 42 votes
    1y

    What about HostBuddy.ai ? Wouldn't that be a good solution for most guest communication ? I've been considering it for my own airbnbs 

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  • Andrew Street
    Member since 2019 · 1k+ posts · 292 votes
    1y

    We use a mix of both. AI handles the common/quick questions through our PMS, and a VA manages anything that needs a personal touch.

    2Reply
  • Collin HaysBusiness Member
    Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
    1y

    I wonder if there is a way to insert some sort of subliminal message inside our photos and/or text to encourage folks to book direct?   Like the "Eat Popcorn" message they used to use subliminally at the movies?

    [email protected]806-672-7102
    SMOKY MOUNTAIN FALLS INC.51 Review
    WebsiteView Page
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  • Garrett BrownPro Member
    Rental Property Investor · Houston, TX · Member since 2024 · 514 posts · 553 votes
    1y

    I use a mix of HostBuddy AI and VAs from South/Central America and the Philippines. 

    They both have pros and cons, but training well with clearly documented SOPs is crucial. Are most of your bookings on Airbnb/VRBO or Direct? Airbnb is much easier to use AI for because most guests just message instead of call. I do about 75% direct, and they LOVE to call. VAs are way better at handling this (AI call services are horrible still I've seen). 

    Happy to connect you if you dm me to any resource I can help with. 

    [email protected]
    BiggerPockets
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  • Myka Artis
    Rental Property Investor · Arlington, TX · Member since 2016 · 706 posts · 611 votes
    1y

    I use both, but the best thing you can have is a VA that knows how to use AI efficiently. We recently upgraded to the $200/mo version of ChatGPT and have our VA creating agents and learning how to be proficient in AI and handle all these tasks.

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  • Garrett BrownPro Member
    Rental Property Investor · Houston, TX · Member since 2024 · 514 posts · 553 votes
    1y

    @Myka Artis how is the $200 version? I've considered it in a similar use but wasn't sure if it was worth the massive price difference. What are you using it for at a high level? Would love to hear your insight 

    [email protected]
    BiggerPockets
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  • Myka Artis
    Rental Property Investor · Arlington, TX · Member since 2016 · 706 posts · 611 votes
    1y

    @Garrett Brown Great question. We have multiple facets to our business. We have the timeshare arbitrage side and the management/operation side. The timeshare management side has always been time-intensive, but it is now largely outsourced, with our AI agents utilized through ChatGPT. We then have our operational side, where our VA uses these tools for any tasks that require them, and also creates any necessary agents.

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  • Lydia Oyetunji
    Virtual Assistant · Atlanta, GA · Member since 2026 · 5 posts · 3 votes
    8mo

    It’s usually not AI vs VA—it’s both, with clear roles.

    AI works well as the first layer for FAQs, instant responses, tagging conversations, and keeping follow-ups from slipping. A VA should be the second layer for anything that needs judgment—tone, complaints, special requests, or coordination with cleaners/maintenance.

    Where setups fail is using AI without guardrails or expecting a VA to manage volume without systems. Pairing a VA with AI-supported workflows keeps response times fast and reduces review risk without losing the human touch.

    The right mix really depends on portfolio size and how many platforms you’re managing.

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