Hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels.

Pricing starts at US$29/month, and all hosts get a 14-day free trial. There are no onboarding fees, no contracts, and no commitments. 

Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in. Hospitable also connects with popular 3rd party booking channels Airbnb, Vrbo, Booking.com, Agoda, and Google Vacation Rentals.

Hospitable

Understanding taxes starts with knowing what applies to you, and what doesn’t. In this session, we’ll look at the broader tax and compliance landscape for US-based short-term rental hosts, with a focus on how investors and experienced operators approach compliance decisions.

This event features **Amanda Han** and **Matt MacFarland**, both Managing Directors at Keystone CPA, and is hosted by **Brandon Huetteman**, Hospitable’s Accountant in Residence. Together, they’ll share how tax professionals think about STR planning, structure, and common red flags, all before things get complicated.

We’ll cover:

*   How STR activity is generally treated from a tax perspective
*   The STR “loophole”, how it’s commonly misunderstood, and the red flags hosts should be aware of
*   Business structure considerations, including the role of LLCs
*   How experienced investors approach tax planning and compliance

The session will begin with a guided discussion, followed by ample time for moderated Q\&A.

**About:**

Amanda Han and Matt MacFarland are founders of Keystone CPA, where they advise real estate investors on tax strategy, structuring, and long-term planning. As both CPAs and investors, they focus on helping hosts and investors keep more of what they earn through thoughtful entity setup and tax planning. They are co-authors of the bestselling book "Tax Strategies for the Savvy Real Estate Investor", and frequent speakers and contributors across the real estate investing community.

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*This session is part of ****Hospitable Unlocked: US Taxes & Compliance****, a three-part series designed to help US-based short-term rental hosts develop a clearer, more confident understanding of taxes and compliance.*

1.  *The STR Tax & Compliance Map (US) (February 10)*
2.  *STR Taxes 101 (US): Income, Expenses, and Depreciation (February 24)*
3.  *Staying Compliant All Year with Hospitable (March 10)*


The STR Tax & Compliance Map (US)

Join us for 3 days of **100% action-focused workshops.** We’ve invited top short-term rental experts from a variety of fields to teach you success tactics you can put to use *immediately*. And yes, it’s completely free.

We'll have 12 separate 45-minute sessions across 3 days. Register now and pick and choose what you attend live. Recordings will be emailed to registrants after the event.


Day 3: STR Success Action Plan - Hospitable Workshop Days

Join us for 3 days of 100% action-focused workshops. We’ve invited top short-term rental experts from a variety of fields to teach you success tactics you can put to use *immediately*. And yes, it’s completely free.

We'll have 12 separate 45-minute sessions across 3 days. Register now and pick and choose what you attend live. Recordings will be emailed to registrants after the event.


Day 2: STR Success Action Plan - Hospitable Workshop Days

Join Hospitable for a live Q\&A designed for hosts with US tax obligations, where we’ll walk through the 1099 and income reporting information Hospitable provides ahead of filing season, and clarify what’s still your responsibility as a host. Led by Abby, our Senior Product Manager for Direct, and Brandon, our Accountant in Residence, this session will help you understand how to use Hospitable’s reports, avoid common misconceptions, and feel more confident heading into tax time.


US Tax Reporting Q&A

Understanding taxes is one thing. Managing them consistently throughout the year is another.

In this final session (3/3), we’ll focus on how US-based short-term rental hosts can approach reporting and compliance as an ongoing process, and how different hosting setups influence what’s required.

We’ll cover:

*   How tax and reporting responsibilities differ across Hospitable plans, including Direct Basic and Direct Premium
*   What it means for Hospitable to be the merchant of record, and how that affects tax handling
*   What hosts can generally expect from tax reporting, including concepts like 1099-Ks and annual earnings summaries
*   How Hospitable supports reporting and record keeping, including integrations with tools like QuickBooks Online
*   Considerations for hosts operating as owners, arbitrage operators, or property managers

This session brings the series together by connecting earlier concepts with day-to-day workflows and reporting practices.

Additional materials and follow-up resources will be shared with Hospitable customers in the [Community](https://community.hospitable.com/).

—

*This session is part of ****Hospitable Unlocked: US Taxes & Compliance****, a three-part series designed to help US-based short-term rental hosts develop a clearer, more confident understanding of taxes and compliance.*

1.  *The STR Tax & Compliance Map (US) (February 10)*
2.  *STR Taxes 101 (US): Income, Expenses, and Depreciation (February 24)*
3.  *Staying Compliant All Year with Hospitable (March 10)*

More information you can find in Hospitable Hosts Community [here](https://community.hospitable.com/hospitable-community-updates-38/hospitable-unlocked-us-taxes-compliance-1134).


Staying Compliant All Year with Hospitable

Speaker

Brandon Huetteman

Accountant in Residence

Replays

The STR Tax & Compliance Map (US)

Day 3: STR Success Action Plan - Hospitable Workshop Days