How Experienced Operators Keep Their Mid-Term Rentals Booked

In Episode 91 of the JV Podcast, Jesse Vasquez sits down with James, who manages 27 active mid-term rental units across Northern and Central New Jersey, to discuss how to fill vacancies and generate more rental leads.They cover Airbnb and Furnished Finder listing optimisation, rental pricing strategies, guest follow-ups, corporate housing leads, and referrals. James also shares how to turn old inquiries into bookings, connect with local businesses, and build relationships with other rental operators.The conversation explores when to accept bookings in advance, when to lower prices, and why relying entirely on platforms like Airbnb and Furnished Finder can be risky. Learn how to build direct booking sources and create a more sustainable mid-term rental business.Timestamps:00:00 What to Expect in This Episode00:48 Why Your Mid-Term Rental Is Sitting Vacant01:52 Inside a 27-Unit Mid-Term Rental Business04:10 How to Optimise Your Rental Listings06:30 How to Identify Low Demand vs. Pricing Problems09:10 How to Choose the Right Property for Mid-Term Rentals14:16 Should You Accept Mid-Term Rental Bookings Months in Advance?18:23 How to Follow Up With Rental Leads22:15 How to Fill Vacant Mid-Term Rental Dates24:24 How to Get More Referrals From Rental Guests27:20 When Should You Lower Your Rental Prices?30:37 3 Ways to Get Your Mid-Term Rental Booked32:54 How to Research Competitor Prices and Rental Demand34:20 Why Fast Lead Response Gets More Rental Bookings37:38 How to Build a Network of Mid-Term Rental Operators45:05 The Simple Strategy Most MTR Operators Overlook47:06 3 Practical Ways to Get More Rental Bookings50:22 How to Diagnose Demand and Generate More Leads52:22 Airbnb and Furnished Finder Updates You Should Know54:00 Why You Shouldn't Depend on One Rental Platform◻️ Host - Jesse Vasquez (Founder of AirVenture Academy)◻️ Guest - James Hwang (Co-founder of Stellar Housing Solutions)

In this Episode of JV Pod, Jesse Vasquez sits down with Candice to explore short-term vs. mid-term rentals and what drives rental property profitability. Learn how to calculate real profits after cleaning fees and operating expenses, attract corporate housing and insurance housing clients, secure direct bookings, and find mid-term rental opportunities. Timestamps:00:00 Why Short-Term Rental Hosts Are Switching to Mid-Term Rentals01:20 When Candice Decided to Pivot Her Rental Strategy02:30 How to Identify Rental Demand in Your Market03:27 Managing 12 Furnished Rental Properties04:12 The Problem With Depending on Airbnb06:20 Short-Term vs. Mid-Term Rental Profitability08:30 Understanding Rental Expenses and Cash Flow09:12 The Two Things She Would Do Differently While Staring Off10:38 How to Turn Airbnb Guests Into Direct Bookings11:38 Why Marketing Matters in Mid-Term Rentals12:50 How to Research Local Demand in Person15:42 The Difference Between a Hotel and a Property19:26 The Advantages of Switching to Mid-Term Rentals20:12 Why Mid-Term Rentals Require Less Guest Communication22:12 What are the 3 Things That You Should Not Do 24:34 Building Relationships Beyond Booking Platforms25:00 How to Connect with Candice26:20 Candice’s Advice for New Mid-Term Rental Operators◻️ Host - Jesse Vasquez (Founder of AirVenture Academy)◻️ Guest - Candice Menard (Long-term Property Manager, Host, and Realtor)

Welcome to Ep. 89 of the JV Pod and in this episode, Jesse Vasquez sits down with Michael Elefante, a successful short-term rental entrepreneur, to discuss how Airbnb investing has changed, why competition is increasing, and what investors need to do to stay profitable. From Airbnb investing and short-term rental strategies to market research, property selection, and scaling a rental business, Michael shares lessons from his entrepreneurial journey and explains why the strategies that worked in 2017 may not deliver the same results today.◻️ Host: Jesse Vasquez (Founder of AirVenture Academy)◻️ Guest: Michael Elefante (Short Term Rental Educator)00:00 Airbnb Investing in 2026: What Has Changed?00:48 Why the Old Airbnb Investment Strategy No Longer Works03:20 Airbnb Market Research: How to Find Profitable Properties06:35 The Biggest Airbnb Investment Mistake Beginners Make07:23 How to Increase Airbnb Profitability on a Budget08:00 How to Find Profitable Short-Term Rental Markets10:35 Building Systems for a Successful Airbnb Business11:20 How to Run an Airbnb Business Without Constant Stress15:20 Why Reinvesting in Your Business Helps You Grow17:28 How Mentorship Helped Scale a Real Estate Business19:40 Is Real Estate Investing Coaching Worth It?21:50 The Biggest Mistake New Airbnb Investors Make24:45 Entrepreneurship, Family, and Building a Business27:40 How Does it Feel to Build a Business With Your Spouse31:22 How to Build a Real Estate Business With Multiple Revenue Streams33:35 Is Real Estate Coaching Still Profitable in 2026?35:05 Inside Michael Elefante's Real Estate Business Empire38:28 Why Attention and Personal Branding Matter in Business40:35 The Biggest Real Estate Investment Michael Would Make Again41:25 How to Build and Scale a Real Estate Business43:32 A Quick Rapid Fire with Michael 45:00 Where to Follow Michael Elefante#realestate #airbnb#rentalbusiness#realestatepodcast#rentalmarket

In this Episode 88 of JV Pod, Jesse Vasquez breaks down the 7 essential things every beginner needs to know about mid-term rental investing, rental property management, and building a profitable rental business.Doesn't matter if you are transitioning from long-term rentals, short-term rentals, or starting your first investment property, discover how to simplify operations and avoid common beginner mistakes. Jesse also explains how to identify your ideal renters and explore corporate housing opportunities through companies, hospitals, and other organizations.00:00 7 Things Every New Mid-Term Rental Operator Needs to Know02:25 Banking and Rental Property Finances06:45 Mid-Term Rental Leases: What to Include09:20 Security Deposits and Tenant Screening11:20 The Tenant Screening Process, Step by Step14:25 Furnishing a Mid-Term Rental Without Overspending17:20 Essential Tools for Rental Property Management20:55 How to Price a Mid-Term Rental23:10 Compare Your Rental to Hotels and Corporate Housing25:40 How to Get Mid-Term Rental Bookings27:22 How to Find More Than Travel Nurse Bookings28:45 Building a Corporate Housing Business Without Owning Property

In this Ep. 87, Jesse Vasquez breaks down mid-term rental burnout, the booking cycle, and the habits that keep rental property investors stuck in panic, overwork, and short-term thinking. Learn why relying on Airbnb, panic pricing, consuming too much content, and operating without backend systems can hurt your rental business.Jesse also explains how to use booked time to build systems, track leads, develop corporate housing relationships, use AI for outreach, and think like a real estate business owner and not just a host.Host: Jesse Vasquez (Founder of AirVenture Academy)00:00 What Mid-Term Rental Burnout Looks Like01:06 How Jesse Started Building a Mid-Term Rental Business02:10 The Mid-Term Rental Burnout Cycle05:30 Hope, Panic, Hustle & Relief07:08 Why Mid-Term Rentals Are a Compound Business10:00 Why Relying on Airbnb Can Cause Burnout13:02 4 Common Mid-Term Rental Burnout Traps16:30 How to Avoid Burnout in Your Rental Business18:48 Build Your Rental Business Like a Business20:50 Think Like a Business Owner, Not Just a Host23:00The Real Cause of Mid-Term Rental Burnout

The mid-term rental market is changing, and the old strategy of listing a property on Airbnb or Furnished Finder and waiting for bookings isn’t enough anymore. In this episode of The JV Podcast, Jesse Vasquez breaks down how to build a stronger mid-term rental business by focusing on relationships and real rental demand. He explains how to find opportunities through corporations, insurance housing, relocation companies, construction projects, healthcare professionals, and corporate travelers. Jesse also shares why mid-term rentals are a housing business, how to uncover hidden rental demand in your market, and how one corporate relationship can create opportunities across multiple markets. Host: Jesse Vasquez (Founder of AirVenture Academy)00:00 Mid-Term Rentals Are No Longer a Niche01:52 Mid-Term Rental Demand Has Grown 136%04:15 The Biggest Mistake: Listing & Waiting for Bookings08:05 Mid-Term Rentals Are a Housing Business, Not a Listing Business09:12 How to Find Hidden Rental Demand in Your Market10:53 Where Corporate & Insurance Housing Demand Comes From14:26 How One Corporate Relationship Can Scale Across Markets16:30 The Future of Mid-Term Rentals: Relationships + Demand

What makes a property actually work for mid-term rentals? In this episode 85, Jesse Vasquez breaks down how to evaluate a rental property before buying or arbitraging it. Jesse shares the four factors every real estate investor should understand: location, layout, numbers, and furnishings. He explains how hospitals, colleges, construction, jobs, and major infrastructure can create mid-term rental demand, why vacation markets aren’t always ideal, and how to analyze the numbers before committing to a property.Through this Podcast, you will also learn how to choose the right investment property, build a pipeline to reduce vacancy, understand corporate housing demand, and create a comfortable furnished rental that works for 30+ day stays.Host: Jesse Vasquez (Founder of AirVenture Academy)⏱️ Timestamps:00:00 What Makes a Property Work for Mid-Term Rentals?02:36 The 4 Things That Make a Winning Rental Property03:25 Location: Why Hospitals Matter for Mid-Term Rentals05:10 Why You Shouldn’t Chase Vacation Rental Markets06:38 Layout: The Best Property Types for Mid-Term Rentals09:18 Numbers: The Rental Property Numbers You Need to Hit13:26 Why a Property Can Look Great on Airbnb but Fail as an MTR15:22 Furnishing: How to Furnish a Mid-Term Rental Without Overspending16:30 How to Reduce Vacancy Before Your Property Is Ready18:00 How to be 90% Ahead of all the Operators

Santonio Cathery went from his first mid-term rental to 14 units, building a corporate housing business that now generates $20K+ per month. In this episode, he breaks down how he used systems, rental arbitrage, relationships, and corporate housing demand to scale his rental business and eventually leave his six-figure job.Anyone into mid-term rentals, real estate investing, rental properties, corporate housing, rental arbitrage, or building a scalable rental business, this episode is packed with practical lessons from Santonio’s journey.▫️ Host - Jesse Vasquez (Founder of AirVenture Academy)▫️ Guest - Santonio Cathery (Founder of SLC Corporate Housing)#realestateinvesting #midtermrentals#rentalbusiness#corporatehousing#realestate

Most entrepreneurs think working harder is the fastest path to success. But what happens when ambition turns into burnout?In Episode 83 of the JV Pod, Jesse Vasquez sits down with Mallory Rowan to unpack her experience with entrepreneurship, burnout, ambition, and building wealth without sacrificing your health and identity.At just 24, Mallory burned out after years of pushing herself through competitive powerlifting, a growing business, and an intense “hustle” mindset. She experienced physical symptoms, financial pressure, and eventually reached a point where she felt like she had lost her personality and her spark.But burnout became a turning point.Mallory explains how stepping back from her first business changed the way she thought about money, business, investing, and success. She shares how creating a simple baseline income through social media management gave her the freedom to pause, rethink her path, and figure out what she actually wanted.The conversation also dives into how to tell the difference between burnout and outgrowing your business, why slowing down doesn’t necessarily mean losing your ambition, how to separate your identity from your business, and the “Toddler Test” she uses to uncover what she really wants.For entrepreneurs, business owners, investors, and anyone feeling stuck in the cycle of hustle and productivity, this episode offers a different perspective on what sustainable success can actually look like.▫️ Guest: Mallory Rowan (Entrepreneur)▫️ Host: Jesse Vasquez (Founder of AirVenture Academy)#entrepreneurship#burnout#business#investing#realestate

Most midterm rental investors assume small towns have no demand. But population doesn’t equal demand.In Episode 82 of the JV Pod, Jesse Vasquez breaks down how he built a successful midterm rental portfolio in California’s Central Valley by identifying corporate housing demand that most operators completely overlook.From travel nurses and engineers to construction workers, displaced families, and corporate employees, Jesse explains where the real demand comes from and how to find it in markets that don’t look attractive at first.He also shares how he landed a multi-year contract with one of the largest wine distributors in the US and filled six properties with 30 engineers from a single conversation.For anyone interested in midterm rental investing, corporate housing, furnished rentals, real estate investing, rental property management, or building a midterm rental business, this episode will show you how to stop thinking like a host and start thinking like an operator.🟡 Join the AirVenture Academy: airventureacademy.com/?🟡 Join the PLACED Cohort: https://mtr.airventureacademy.com/placed▫️ Host: Jesse Vasquez (Founder of AirVenture Academy)#midtermrentals#rentalbusiness#corporatehousing#business#investing