Best Short Term Rental Business Coaches & Courses [2022]

July 23, 2022 | Amelia Melching

At Wheelhouse, our mission is to help short-term and vacation rental owners improve revenue and scale their portfolio. We do this through our dynamic pricing software that allows our customers to get pricing specific to seasonality, day of week trends, and even actual sales in the market. 

But, we know there’s a lot more to success in the vacation rental market–which is why we love learning from and sharing the best short-term rental business coaches and courses out there.

What can short-term rental courses do for your business?

Executive coach, life coach, relationship coach — there’s a coach for everything, including short-term rental businesses. 

Why is it so common for people to have a coach? One branding expert attributes their popularity to an unprecedented need to navigate immense change; a feat coaches help with. Courses are also useful, especially ones that capture proven income strategies and latest trends. 

What’s great about 2022 is the sheer availability of tools to enhance your business. From revenue management tools to property management software, coaches and courses are just another option for you to keep profits growing. 

Here’s why:

Best Short Term Vacation Rental Coaches & Courses



Known as the King of Airbnb, Brian Page helps people leverage automation to work part-time in the short-term rental business and discusses making money through Airbnb through rentals, not owned property. 

The BnB Formula is a 3-6 month coaching program where Page works 1:1 with clients to enhance their Airbnb portfolios and business. It includes a masterclass, a collection of tools and templates, and access to a private Facebook community of like-minded entrepreneurs. 

Page has 100,000 students across the world studying his BnB formula. However, he advises on more than just the real estate industry, including affiliate marketing, cryptocurrency, and stock trading.

Pricing: Starts at $1,997

Cashflow Diary


Cashflow Diary features hospitality training for aspiring short-term rental managers that want to succeed without buying property. Founder J. Massey is a successful entrepreneur and family man who found financial freedom (retired at 38) through investing in Airbnb short-term rentals. Today, his portfolio consists of 34 units that make him more money than anything he’s ever embarked on in his business experience.

Massey’s training business features all sorts of juicy resources, from regular blog posts noting industry trends, to a weekly podcast. He also offers free, short training courses and videos on topics like marketing, staffing, financing, and revenue management. Finally, his course titled “Short-Term Rental Business Blueprint” is absolutely free and tailored to the beginner STR manager. 

Massey’s 12-month coaching and mentoring program is less advertised and doesn’t list a price.

Awards, Recognition, or Results: Testimonials from customers detailing enhanced revenue and occupancy after participating in Cash Flow Diary resources. 

Pricing: Free course, coaching price not listed

The Fearless Investor


The Fearless Investor is a collection of real estate education services by Kyle Stanley. His background in health and wellness, sales, recruitment, and television offer a unique perspective, but his true success started with using Airbnb to pay off his mortgage. 

A few investments, coaching sessions, seminars, and “flips,” later, Kyle fashioned his modest Airbnb listing into a $25,000-monthly revenue machine. 

Today, he offers a few products:

Awards, Recognition, or Results: Testimonials detailing $160,000 in yearly revenue, success convincing landlords to allow Airbnb businesses, and more. 

Pricing: Not listed

Million Dollar Renter


Million Dollar Renter is an education business that specializes in supporting short-term rental managers that rent their properties. However, they also cover property acquisition for interested investors. The program currently offers five specialized courses on the short-term rental business: 

Sean Rakidzich owns the business and also runs a YouTube channel called Airbnb Automated. 

How it works: Self-paced, video-based courses

Awards, Recognition, or Results: Testimonials detailing new property acquisitions, increased revenue, and more occupancy

Pricing: Course prices range anywhere from free to $4,000

Rental Scale-Up


Rental Scale-up offers regular tutorials on various short-term rental topics, like optimization strategies, cleaning tips, crisis management, and more. 

A trusted source for short-term rental news, Scale-Up features regular blog articles, newsletters, and reviews on the latest trends in the industry. For example, they feature some top pricing tools like Wheelhouse in the website’s Airbnb tools section. 

The site also has a dedicated industry news section categorized by booking websites, including one for Airbnb, VRBO, and 

As for courses, Rental Scale-up offers various consulting and course packages, like:

Pricing: Ranges from free to thousands of dollars for more intense consultation packages

Short Term Sage


Julian and Jon run Short-term Sage, a company dedicated to helping everyday people find financial freedom through Airbnb. A key principle is their stance that you don’t have to own property to succeed in the short-term rental business. 

Both hosts had humble beginnings with Airbnb starting with a small basement rental. The pair found success first with a short-term rental podcast, then quickly moved on to offer a free training course that covers:

Awards, Recognition, or Results: Countless video testimonials detailing success with starting an Airbnb/short-term rental business, increasing occupancy, finding efficiencies, etc. 

Pricing: Free

Learn More

The Whole Hearted Host


Hosted by Tracey Northcott Consulting, the Whole Hearted Host is a course that features various branding and monetizing strategies for Airbnb hosts. Tracey stumbled upon Airbnb as an income source by accident but quickly grew to run a 7-figure business with staff in Tokyo. 

Now, she offers top-notch consulting for aspiring short-term rental business owners both within and outside Airbnb. 

The course lasts six weeks and covers branding, guest screening, profitability, marketing, monetization hacks, and more. Moreover, she also offers a completely free masterclass about writing the perfect listing bio. 

Tracey’s unique lens into the Japanese real estate market is rare in short-term rental coaching.


Brindy is an Airbnb Ambassador, designer extraordinaire & business coach.  In short, she is able to help you with the needs of your business, end-to-end.  And, you are sure to have a blast while working with her! 

As Brindy shares, she loves working with people who, “know hitting income goals- and so much more – depends on your approach.”

Brindy can you help with:

– Define & perfect your strategy

– Walk you through the legal aspects of your business

– Teach you how to create an aesthetically pleasing space

– Manage your portfolio

– Create an excellent hospitality experience for your guest.

Learn more here:

What is included in short-term rental courses and with coaches?

Conclusion: Continue Optimizing your Short Term Rental Business

Courses and coaches allow short-term rental business owners to learn from experienced owners who have already seen success and know how to help you get there. 

But of course, getting this success yourself can always use additional support, through other vacation management software like Wheelhouse. Wheelhouse is a pricing tool for every type of real estate investor—hobby hosts, advanced owners, and professional property owners. The software includes an adaptable pricing tool, market insights, competition data monitoring, and ultimate customization capabilities.

In fact, most of the above courses and coaches touch upon dynamic pricing to some degree. Ready to see it in practice? Start earning 40% more per month with Wheelhouse!