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Guest Portal users earn $20 per booking with Trip Insurance

  • January 16, 2026
  • 7 replies
  • 840 views
Tim Parry
Hospitable Team Member
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We’re excited to announce that Trip Insurance is now generally available for all U.S. properties with access to Upsells.

Trip Insurance is provided by RentalGuardian and is offered directly to eligible guests inside the Guest Portal up until day before check-in. It gives guests peace of mind while generating commission for you on every policy sold. So far, one host has earned $190 in commission from a single booking - paying for their monthly Hospitable subscription three times over.

The Trip Insurance upsell is automatically enabled, and there’s nothing you need to do. It runs entirely in the background, and you can switch it off at any time under Guest Experience → Upsells if you prefer.

To give guests access, make sure you’re directing them to the Guest Portal via the %guest_portal% shortcode in your new reservation message. That’s the only place Trip Insurance can be purchased, and it’s also where guests complete other important steps like rental agreements, verification, and security deposits.

If you’d like to learn more about how Trip Insurance works, you can view our help article here, and see the walkthrough demo here

7 replies

Petra Podobnik
Hospitable Team Member
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  • Hospitable Team Member
  • January 16, 2026

@Mikey I think you mentioned at some point that it would be great to offer trip insurance, but I’m not 100% sure anymore and couldn’t find the post. Tagging you just in case that did happen, and so you can make sure to offer this as an upsell to your guests if you're still interested. 💜


Miles Hobson
Hospitable Team Member
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  • Hospitable Team Member
  • January 16, 2026

To give guests access, make sure you’re directing them to the Guest Portal via the %guest_portal% shortcode in your new reservation message.


A must do if you have US properties! Add a simple shortcode, earn an extra $20 per booking on average 🤑


R4z0R
New Participant
  • New Participant
  • January 17, 2026

Will it also be available in Europe?


sati
Participating Frequently
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  • Participating Frequently
  • January 17, 2026

I am adding the “upsale” short cut to my arrival details to offer early checkin. Will the travel insurance show up with this link or does it need the “guest portal” short cut? 


Krista Rica
Participating Frequently
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  • Participating Frequently
  • January 19, 2026

Great news!  we are located in Costa Rica and I did have a guest purchase trip insurance. So I’m hopeful coverage is also in Costa Rica?  Where does it show up if we’ve earned a commission?  And does the commission only show up after check-in?


Tim Parry
Hospitable Team Member
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  • Author
  • Hospitable Team Member
  • January 20, 2026

Hi all! Just answering these questions below :) 

 

Will it also be available in Europe?

 

Currently exploring this possibility!

 

 

I am adding the “upsale” short cut to my arrival details to offer early checkin. Will the travel insurance show up with this link or does it need the “guest portal” short cut? 

 

The %upsell% shortcode will deep route into Upsells in the guest portal, whereas Trip insurance can be found from the home page. Guest Portal shortcode would be better here to show guests both the Upsell & Trip insurance options.

 

 

Great news!  we are located in Costa Rica and I did have a guest purchase trip insurance. So I’m hopeful coverage is also in Costa Rica?  Where does it show up if we’ve earned a commission?  And does the commission only show up after check-in?

 

Coverage is based on the guest’s location, not the property location - we ask their location during purchase to make sure we can provide coverage.

You should see an Upsell purchased icon in the inbox on the reservation where they purchased? Clicking this will show you any commission earned, which will be added as a scheduled payout after check-in!

 

 


Ryan Moyer
Known Participant
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  • Known Participant
  • January 20, 2026

Is there a shortcode to send them directly to the travel insurance checkout rather than the guest portal?

Can the travel insurance be added to the upsells page (instead of a separate line on guest portal)?