This episode features Tim Rosolio, Vice President of Partner Success at Expedia Group/VRBO. Tim joins T and T to discuss the wildly successful VRBO Fiesta Bowl. This episode covers topics related to Vacation Rental Partner Success, Marketing and Branding, and Sports Sponsorship. It also includes a segment of Rapid Fire Q&A with Tim which is hilarious.

Takeaways

• Vacation Rental Partner Success
• Marketing and Branding
• Sports Sponsorship

Chapters

• 00:00 Introduction and Predictions
• 14:27 Sports Sponsorship
• 31:42 Rapid Fire Q&A

The conversation delves into the role of AI in vacation rentals, focusing on its impact on property management and the future of human work. It explores the potential of AI to revolutionize the industry and the need for property managers to adapt to the changing landscape. The discussion also highlights the importance of understanding and leveraging AI tools to enhance the guest experience and drive direct bookings.

Takeaways

• AI in Vacation Rentals
• Impact of AI on Property Management

Chapters

• 00:00 Introduction to AI in Vacation Rentals
• 07:04 The Impact of AI on Human Work
• 17:01 The Future of AI in Property Management

We share the most useful lessons from 2025 and stack them against bold, data-backed predictions for 2026. Guests from data, software, brokerage, and luxury operations add a wide lens on AI reliance, flexible stays, regulation, and quality.

• investing time in tools already owned
• doubling down on top performers
• daily hands-on revenue management
• pivoting calendars and cancellation rules
• AI discovery and answer engine optimization
• service quality as the true moat
• regulation readiness in an election year
• K-shaped economy across guests, owners, staff
• short stays rising in a hybrid model
• AI fraud risk and mitigation
• direct booking growth via autonomous marketing
• quality reset and asset preservation

Send us a line. What predictions do you have for 2026?

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Disaster preparation in the vacation rental industry typically focuses on protecting properties and communicating with owners and guests—but what about the people who make your business run? In this eye-opening episode, Hospitality Heroes co-founder April Burns joins hosts Tim Cafferty and Tiffany Edwards to reveal the five critical mistakes property managers make when planning for natural disasters.

Drawing from her firsthand experience during Hurricane Helene's devastating impact on Western North Carolina, April shares powerful stories of communities cut off from help, families separated during evacuations, and the extraordinary impact that proper preparation could have made. "Superman is not coming," she reminds listeners, underscoring that proactive planning is essential for survival and recovery.

From failing to help employees understand their evacuation options to overlooking the importance of digital documentation backups, these common mistakes can prove catastrophic during emergencies. The conversation explores innovative solutions like cross-regional partnerships between property management companies, creating expanded emergency contact networks, and establishing regional supply caches with specialized equipment beyond just water donations.

The discussion extends beyond theory to practical action steps, including how vacation rental managers can immediately improve their disaster readiness using resources available at HospitalityHeroes.org. You'll discover why expanding your emergency planning to include housekeepers, vendors, and community partners isn't just compassionate—it's essential for business continuity.

Whether you manage properties in hurricane zones, wildfire regions, or flood-prone areas, this episode provides crucial insights for protecting your team and business when disaster strikes. Remember: "It's not a matter of if it's going to happen. It's a matter of when."

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Unlock the secrets of personal and professional growth in the vacation rental industry as Tiffany Edwards takes us behind the scenes at the Vacation Rental Women's Summit in Charleston. This intimate conference delivers powerful insights that transcend traditional hospitality concepts, focusing on creating meaningful experiences not just for guests, but within your own team.

What happens when you bring together the industry's most innovative minds in an environment designed for authentic sharing? Magic. From discussions about building "relentless generosity" into your business model to practical approaches for nurturing your company culture, this episode reveals how top performers are reimagining what hospitality means in 2024.

Technology takes center stage as we explore cutting-edge applications transforming the vacation rental landscape. Imagine reservations negotiated bot-to-bot, AI-generated property upgrades to inspire owner investments, and virtual worlds where guests interact with your brand. Despite these advancements, our guests remind us that the human element remains irreplaceable—technology should enhance, not replace, the personal connections that define true hospitality.

The most profound moments come through stories of resilience, particularly from managers who've weathered disasters like the Lahaina fires. These powerful testimonials highlight how emotional fortitude is just as important as business strategy when facing industry challenges. As one veteran operator suggests, sometimes we need to "repot" ourselves—acknowledging when we've outgrown our current container and need space for new growth.

Whether you're managing properties in Key West or Kauai, this episode delivers actionable insights on creating exceptional experiences while nurturing your team and yourself. Join Tim and Tiffany as they unlock the keys to vacation rental success through the wisdom of industry leaders who are redefining what's possible in our rapidly evolving space.

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The vacation rental landscape shifted dramatically during Summer 2025, revealing crucial insights for managers navigating this new terrain. Tim Cafferty and Tiffany Edwards unpack five game-changing trends that defined the season and will likely shape the industry moving forward.

Booking windows have contracted at an unprecedented rate, with a remarkable 42% of July bookings classified as last-minute reservations. This shift isn't subtle—some properties saw booking windows shrink by 6-8 days compared to historical patterns. Revenue management now demands constant vigilance, with successful operators monitoring pricing hourly rather than monthly. Behind this trend lies a perfect storm of economic uncertainty, high credit card debt, and consumers trained to wait for last-minute deals, creating a more calculated approach to vacation planning.

The decision-making process for vacations has undergone a fascinating transformation. Survey data from Walton County, Florida reveals three in five teens now influence vacation planning, while American Express reports 68% of Gen Z and millennial parents involve their children in destination choices. Additionally, specialized group travel—girls' getaways, guys' golf trips, mother-daughter retreats—represents a growing market segment deserving of targeted marketing approaches.

Financial consciousness defines today's traveler. With Americans spending 25% less on vacations according to the Washington Post, guests scrutinize cancellation policies and increasingly leverage reward points to offset costs. Property managers listing through point-based platforms like Marriott Homes & Villas have seen revenue increases of up to 15%, suggesting strategic opportunities in how properties are positioned and marketed.

The podcast also explores the critical importance of pre-season maintenance programs. Properties implementing comprehensive spring inspections—focusing particularly on HVAC systems, sliding doors, and appliances—reported dramatically fewer peak-season emergencies, preserving guest satisfaction and avoiding costly refunds during high-revenue periods.

Whether you're evaluating new tech vendors or reassessing property owner relationships, this summer offered valuable lessons in partnership management. Join Tim and Tiffany as they share practical strategies for adapting to these evolving dynamics and positioning your vacation rental business for success in the seasons ahead.

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The vacation rental landscape is transforming before our eyes, with shifts that started during pandemic times now cementing themselves as permanent fixtures in our industry. Hosts Tim Cafferty and Tiffany Edwards dive deep into the most significant trends reshaping how successful property managers operate.

Remote work flexibility has fundamentally altered travel patterns. Though some workers have returned to offices, the ability to work from anywhere remains firmly established. Smart vacation rental managers are capitalizing on this by ensuring properties feature proper workspaces, reliable high-speed WiFi, and marketing that specifically targets these "bleisure" travelers. As Tim notes, even transforming underutilized spaces into dedicated office areas can become a powerful differentiating amenity.

Perhaps most striking is the dramatic shortening of booking windows. Both hosts report seeing timeframes cut in half compared to previous years, with Tim sharing a recent booking made just 24 hours before arrival. This requires a hands-on approach to pricing strategy, adjusting rates for remaining inventory without undervaluing properties. "This isn't a slash sale," Tiffany emphasizes - there must always be a threshold below which prices won't drop.

Today's guests also demand more flexible cancellation terms before committing to bookings. While historically some managers maintained strict policies, both hosts have seen positive results from more guest-friendly approaches. Booking platforms are even incentivizing flexibility through algorithm benefits. The numbers consistently show that despite occasional cancellations, the net result of more flexible policies proves positive.

Communication expectations have similarly evolved, with guests strongly preferring text messaging over phone calls. They want control to initiate contact when convenient while expecting prompt responses. Implementing effective texting systems with personalized automated responses has become essential, though interestingly, proactive welcome calls can still create positive impressions precisely because they're unexpected in today's text-dominated world.

The hosts also discuss how social media influences guest expectations, the strategic use of influencer partnerships, and important new FTC regulations requiring transparent pricing across the vacation rental industry.

These trends aren't temporary - they represent permanent shifts in guest behavior. Success now depends on adapting to meet these evolving expectations. Visit TheVacationRentalKeyWithTNT.com or find us on social media to join the conversation and share your experiences navigating these industry changes.

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Ever wondered what amenities truly make a difference in vacation rentals? Tim Cafferty and Tiffany Edwards dive deep into the evolving landscape of guest expectations and how successful property managers are responding.

The days of "bring your own TV" are long gone. Today's vacation rental guests expect a streamlined, hotel-like experience with the comforts of home. Smart TVs with streaming capabilities, reliable high-speed Wi-Fi, and quality linens are no longer luxuries – they're baseline requirements. Tim and Tiffany explore how successful property managers are standardizing these essentials while finding ways to stand out in competitive markets.

Kitchen provisions reveal a critical advantage vacation rentals hold over traditional accommodations. Guests value the ability to prepare meals, but expectations have grown beyond basic cookware. From coffee makers and filters to storage containers and starter supplies, the podcast explores how thoughtful kitchen setups translate directly to guest satisfaction. They share practical advice on inventory management, cost control, and creating consistent experiences across multiple properties.

Beyond the basics, premium amenities create memorable stays that drive repeat bookings. Welcome packages with local wine and charcuterie boards, personalized greeting services, beach chair setups, and mid-stay cleanings can transform a good stay into an extraordinary one. The hosts share strategies for determining which premium touches make sense for your market and how to implement them without breaking your budget or overwhelming your operations.

Whether you're managing a single property or hundreds, this episode offers practical insights to elevate your guest experience while maintaining operational efficiency. Listen now and discover how the right amenity strategy can increase your bookings, drive better reviews, and create loyal "whale" guests who return year after year.