

Short Term Rental Riches
Tim Hubbard
Tim Hubbard, successful investor and CEO of a seven-figure short term rental management company shares it all. The insider tips you need to know to acquiring, operating and scaling a successful short term rental business.
Episodes
Mentioned books
Mar 31, 2026 • 12min
333. VRBO's Big 2026 Update Every STR Host Must Know
If your VRBO bookings have slowed, the problem might not be your property—it could be a major platform shift. VRBO's 2026 update is quietly reshaping how listings get visibility, and most hosts haven't caught on yet. In this episode, we unpack what changed, why it matters, and how to adapt before your competitors do. VRBO's move from portfolio-based to listing-specific Premier Host status—and why it changes everything The 5 exact requirements you must hit to unlock higher visibility and better placement Hidden "visibility tiers" most hosts don't even realize exist (including the top 1%) Why a single bad listing no longer drags down your entire portfolio—and how to leverage that A smart (and slightly unconventional) strategy to rebalance bookings across Airbnb and VRBO This update isn't just a tweak—it's a shift in how visibility, trust, and bookings are earned on VRBO. If you want to stay competitive (and profitable), this is one episode you can't afford to miss. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/
Mar 24, 2026 • 27min
332. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 2)
The short-term rental game is evolving fast—and staying ahead means asking better questions. In this live Q&A, we dive into real challenges operators are facing right now—from AI tools and hiring to market shifts and scaling pains. If you're growing (or thinking about it), this episode uncovers what's working today… and what could be holding you back. Key Takeaways: How AI is transforming guest communication, inspections, and operational efficiency The fastest way to find reliable local cleaners and maintenance teams (hint: it's easier than you think) What actually changes when scaling from 5 to 15 properties—and where most people fail Why 1–2 bedroom properties may no longer be the "easy win" in today's market The pricing mistakes (like cleaning fees & damage waivers) that quietly kill your bookings Whether you're just starting or scaling fast, this episode is packed with real-world insights you can apply immediately. Don't fall behind as the market shifts—stay informed, stay optimized, and stay competitive. Be sure to subscribe, share with a fellow host, and explore the resources below to level up your STR game. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/
7 snips
Mar 17, 2026 • 22min
331. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 1)
Live Q&A explores dynamic pricing pitfalls and why scraped market data can mislead revenue strategies. They highlight overlooked signals like reviews and new-listing handicaps. Conversation covers when to enable dynamic pricing and what separates top-performing properties. AI for guest messaging is debated, with limits on full automation and complex workflows that still need human touch.
Mar 10, 2026 • 15min
330. How to Allow Pets Without Risking Your Short Term Rental Property
Short-term rental hosts are divided on one big question: should you allow pets in your property? While some hosts see massive boosts in visibility and bookings, others worry about damage, cleaning headaches, and insurance issues. In this episode, we break down the real pros, cons, and strategies behind pet-friendly listings—and what every host should consider before flipping that pet-friendly switch. Why allowing pets can instantly increase your listing visibility and reduce competition in many markets The smartest ways to structure pet fees on Airbnb, VRBO, and Booking.com without hurting bookings Essential pet rules every host should include in their house rules or rental agreement Damage protection strategies, deposits, and insurance considerations when hosting pets The critical difference between service animals and emotional support animals—and what hosts can legally ask Allowing pets can be a powerful strategy to boost occupancy and stand out in crowded markets—but only if it's done the right way. From setting smart policies to protecting your property, this episode walks you through everything you need to decide if pet-friendly hosting is the right move for your rental business. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/
Mar 3, 2026 • 14min
329. The Airbnb Rules That Have Completely Changed in 10 Years
A look back at how Airbnb shifted from personal stays to contactless, hotel-like experiences. Discussion of why culture and scale raised guest expectations. The rise of dynamic pricing and tech as must-haves. How stricter reviews now control search visibility. A fast take on why short-term rentals still compete with long-term investing.
Feb 24, 2026 • 40min
328. These STRs Earn $150K/Year and cost ONLY $300K property
The short-term rental industry is evolving fast—and the strategies that worked five years ago may not cut it today. In this episode, Natalie Palmer shares how she scaled from co-hosting in a single condo complex to raising capital for luxury destination properties. If you're wondering where STR investing is headed next, this conversation might change your approach. How Natalie scaled to 10 co-hosted units in one condo complex—and why that model simplified operations Why housekeepers are your most valuable asset (and how to structure your team for success) The pricing strategy shift that's working in today's more competitive STR market How luxury upstate New York properties are generating $150K–$200K annually at a fraction of major-market purchase prices Why the "middle-tier" STR may disappear—and how to position your property to survive and thrive The STR landscape is shifting—but opportunity is everywhere if you know where to look. Whether you're refining operations, upgrading amenities, or exploring passive investing, this episode is packed with actionable insights. Be sure to subscribe, share with a fellow investor, and explore the resources below to level up your portfolio. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/
15 snips
Feb 17, 2026 • 23min
327. 25 Conferences Later: My Best STR Insights
A fast-paced recap of major industry shifts after 25 conferences. Venture capital quietly snapping up local managers and the move toward luxury listings are highlighted. Processes and SOPs are shown as the backbone of great guest experiences. AI's role in messaging and operations gets attention, plus practical tips on design and prioritizing your top photos for bookings.
9 snips
Feb 10, 2026 • 13min
326. 8 Airbnb Mistakes You Need To STOP Today
They highlight eight common hosting mistakes that quietly hurt bookings and reviews. Topics include guest screening and ID verification, the risk of relying on a single booking channel, where quality furniture matters, and when not to overspend on decor. They also cover careful selection of tech and AI tools, flexible pricing over rigid revenue targets, setting realistic owner expectations, and the need to delegate to scale.
Feb 3, 2026 • 15min
325. Managing 5 Properties vs. 20: The Real Differences
Scaling from a handful of properties to dozens changes everything. The conversation highlights why SOPs, tech, and pricing tools become essential. It digs into staffing, housekeeping logistics, and how delegation affects reviews and revenue. Expect talk about revenue managers, automation for guest communication, and the mindset shifts needed to grow without burning out.
Jan 28, 2026 • 14min
324. The World's Most Extreme Off-Grid Airbnb's
Ever dreamed of sleeping under a glacier or hanging off a cliffside in a glass pod? In this episode, we uncover the world's most extreme short-term rentals and explore why guests are willing to pay top dollar for once-in-a-lifetime experiences. If you're looking to stand out in the saturated STR market, this episode will spark bold ideas. Discover a floating glacier suite in Greenland that charges over $1,000 per night—and why it's worth it Hear a wild story about getting stuck in the Colombian jungle en route to an unforgettable jungle Airbnb Explore what makes guests crave "digital detox" stays and how off-grid rentals are capitalizing on it Dive into a cliffside glass pod in Peru and a shark-surrounded suite in Paris (yes, really) Learn the key factors that make or break guest expectations in extreme rental settings For any STR owner or investor curious about breaking out of the ordinary, this episode is packed with inspiration, real stories, and practical takeaways to elevate your rental strategy. Share it with a friend or leave us a review if you loved it! Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/


