How to get started in short-term rentals

Not sure where to start? Start Here!

Short-term rentals have become a dynamic and lucrative industry, offering a unique blend of hospitality, entrepreneurship, and real estate investing. These furnished lodgings, available for stays of less than 30 days, have revolutionized the way people travel and seek temporary accommodations.

Why Short-Term Rentals?

The allure of short-term rentals transcends traditional real estate investments. Not only do they often yield higher income compared to long-term leasing, but they also offer property owners the chance to enjoy the space while generating revenue. For landlords, short-term rentals can provide an escape from the legal complexities associated with long-term tenants, offering more flexibility and control along with the potential for far greater income. That said, these rentals are definitely are not a passive income stream - outsourcing the work is a great way to make it much more passive though. (See my post about short-term rentals as passive HERE)

Over the years, I've worked closely with literally hundreds of individuals who have successfully entered the short-term rental market, and I've categorized different investor profiles based on their approach - you can learn more HERE, and get insights based on your particular goals and interests borne from my deep experience in the industry. 

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My STR Roapmap comes with a download of my excel analyzer calculator

Navigating the Short-Term Rental Journey

Embarking on a short-term rental venture entails more than just property ownership – it requires a multifaceted skill set. Success requires a grasp of hospitality, marketing, and sales. The appeal of short-term rentals lies not only in their potential for impressive returns but also in the ability to strategically position your property within the market.

  • Acquisition: Finding the right property is crucial. At one time, demand far outstripped supply in most markets. Today, some markets have more supply than demand which makes it much more imperative to learn the art of marketing and niching - hallmarks of a successful short-term rental.  Location, amenities, and local regulations play a pivotal role in determining the success of your short-term rental.  Check out my blog post about data sources for analyzing income potential as well!

  • Setting Up: Transforming your property into an inviting and functional space for guests involves careful planning and furnishing. Attention to detail can lead to rave reviews and repeat bookings, not to mention significantly higher income.  Design for short-term rentals is different than residential design; learn more about design for STR HERE

  • Operations: Managing bookings, guest communication, and maintenance demands organization and efficiency. Outsourcing to a capable operator or mastering these aspects yourself is key.

  • Marketing and Sales: Effectively promoting your short-term rental requires a strong online presence, appealing visuals, and a compelling narrative that resonates with your target audience.  You can outsource much of this to online booking platforms - they come with built in audiences and enable you to find success much sooner than you would marketing your place on your own; but those platforms come at a cost and limit your autonomy as an operator. Even with using those platforms, its a often a crowded market place; understanding how to best position your property within the market is key to success. 

  • Business Backend: Behind the scenes, there's a business to run. From financial management to legal considerations, a solid backend ensures a smooth operation.

  • Quality Control/Risk Management: Ensuring guest satisfaction and safety is paramount. Implementing quality control measures and addressing potential risks are integral to a successful short-term rental. I have a case study HERE where I rented a place that had several safety concerns - which I brought to the owners attention and learned he simply was unaware of the risks - and how you can avoid that rookie mistake. 

  • Portfolio Growth: As you gain experience and traction, you may consider expanding your short-term rental portfolio. Each new property introduces unique opportunities and challenges. I've slowly worked on growing, and leveraged a partnership and private money for my second property - watch the case study HERE.  Portfolio growth is never just about more properties, though - its tax strategies as well.  If you are starting a short-term rental business through arbitrage or similar, then you have an entirely different set of challenges to sort through, too. 

The Road Ahead in Short-Term Rentals

Short-term rentals offer a standout opportunity where property ownership meets hospitality entrepreneurship. However, it's important to recognize that success doesn't happen overnight. Diligence, adaptability, and a commitment to continuous improvement are the cornerstones of a thriving short-term rental business.

As a maturing market, the industry faces many challenges that will flush out in the coming years; from issues in defining the role of short-term rentals within communities juxtaposed with property owner rights, the competence of operators to provide safe lodging, and the role played by the powerhouse booking platforms like AirBNB and VRBO.

In the coming weeks, we'll delve deeper into each phase of the short-term rental journey. Whether you are a landlord considering the income potential of short-term rentals or an aspiring short-term rental host looking to unlock the full potential of your property, stay tuned as we explore the ins and outs of this dynamic industry. Together, we'll uncover the strategies and insights that will set you on the path to short-term rental success.

Just Getting Started? 

The advice I give folks is lean into learning.  Podcasts, books, online content - get clarity about your goal and the path you believe suits you. My investor persona quiz can help you understand the various types of folks out there - its key to understand that advice you may receive or content you stumble across may be from someone whose short-term rental journey has little in common with yours; lots of folks are willing to give advice - just make sure they come from a place you actually want to go.  Check out my Mentors From Afar for ideas of folks and resources I've leveraged in my own journey and grab my 30 page guide - and bonus analyzer spreadsheet to walk you through this process for only $5!!

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Grab YOUR digital Roapmap Today (BOOK50 for 50% OFF)

Not finding what you need? I offer 20 minute calls - no strings, to help you answer your trickiest questions. Some folks go on to work with me - sure (hey, I have to make a living) but some folks just need 20 minutes and I'm happy to connect and learn from you, with you, and help you too. Book a time HERE. 

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Have you identified YOUR STR investor persona? Take the Quiz HERE!

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Kate Stoermer | The CEO Host

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: : short-term rental investing, vacation rental investing