The Hideaways Show

The Hideaways Show

Welcome to The Hideaways Show, where we spotlight the magic of distinctive short-term rentals. Join us twice a week as we interview industry leaders who have mastered the art of creating unforgettable guest experiences. From secluded mountain retreats to charming coastal cottages, we uncover the strategies behind building successful, destination-worthy properties. Get ready to elevate your rental game and create truly remarkable hideaways.

Episodes

July 15, 2025 48 mins

In this edition of the Hideaway Show behind the Curtain edition, hosts Jordan Holmes and Mike Sebastian, also known as Mr. Red River Gorge, delve into the intricacies of building bespoke short-term rentals.

They discuss the initial excitement of breaking ground, the logistical challenges encountered as projects near completion, and the unique joys and frustrations of customizing properties.

Mike shares his journey from bartending to ...

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In this episode of The Hideaways Show: Behind the Curtain, hosts Jordan Holmes and Mike Sebastian dive into the pitfalls of investor complacency and the unexpected costs associated with older rental properties.

They discuss the importance of using data to paint a comprehensive picture for property performance comparisons and the challenges of maintaining top rankings on multiple booking platforms.

Additionally, they explore the appea...

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In this episode of The Hideaway Show 'Behind the Curtain' edition, Jordan Holmes and Mike Sebastian dive into the significance of property reviews, the perks of unique amenities, and the psychology behind choosing one accommodation over another.

They list their top five dream features for Short Term Rentals (STRs) if budget were no issue, including unique water features, container pools, golf simulators, temperature-controll...

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In this episode of The Hideaways Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian explore their adventures in the short-term rental market, focusing on how unique amenities can dramatically transform guest experiences and boost revenue.

They discuss the impact of installing a hot tub at their properties, leading to eye-popping increases in direct bookings and revenue, largely driven by successful social media promotio...

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In this lively episode of The Hideaway Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian catch up after a break, diving into the importance of creating engaging content for short-term rentals (STR).  The conversation transitions into their biggest STR investment mistakes, revealing the pitfalls and lessons learned from financing through a primary residence HELOC and the complications of managing a five-unit property.

T...

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In this edition of The Hideaway Show Behind the Curtain, hosts Jordan Holmes and Mike Sebastian discuss Airbnb's major summer release and its potential impact on the short-term rental market.

They dive into the details of new services offered by Airbnb, such as chef and massage services, and relaunching experiences, portraying Airbnb's vision to be a one-stop platform for all things travel.

The hosts then analyze a troubling article...

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In this episode of The Hideaway Show: Behind the Curtain, hosts Jordan Holmes and Mike Sebastian discuss the challenges and strategies in owning short-term rentals, emphasizing the need for unique properties and business diversification.

They address recent policy changes by Airbnb aimed at preventing hosts from taking guests off-platform, highlighting the importance of not relying solely on any one platform. Practical tips on utili...

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In this edition of the Hideaway Show - Behind the Curtain, hosts Jordan Holmes and Mike Sebastian discuss the exciting developments in their cabin building endeavors. They emphasize the importance of not needing to be perfect from the start and learning from experience.

The main highlight is their daring project of placing a hot tub on top of a boulder at their Rock Haven Hideouts Trio of cabins. They recount the challenges, the inv...

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In this episode of the Hideaway Show, Jordan Holmes interviews Wendy Doris, owner of Mostess Property Management. Wendy shares her journey from flipping houses to managing short-term rentals in Phoenix.

Highlighting the importance of design and branding, Wendy reveals that Mostess' properties, including unique themed homes like 'Swifty' houses dedicated to Taylor Swift fans, prioritize providing unforgettable guest experiences.

She d...

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In this engaging episode of The Hideaway Show, host Jordan sits down with Jandy Salguero, the innovative owner behind Out of Bounds Retreats, which features unique properties in Banner Elk, North Carolina, and Holden Beach.

They delve into Jandy's journey from long-term rentals to short-term beach and mountain retreats, highlighting the pivotal moments, challenges, and triumphs along the way. Discussing the intricacies of managi...

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In this episode of The Hideaway Show, hosts Mike and Jordan share insights and takeaways from the 'Level Up Your Listing' Summit in Phoenix. They discuss the confidence needed to improve in the short-term rental industry and highlight the enhanced experience of doing something multiple times.

The episode reveals their experience with thunderstorm surprises in Phoenix, meeting industry leaders like Seth & Tori Bolt and Is...

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In this episode of The Hideaway Show, hosts Jordan Holmes and Mike Sebastian delve into the importance of diversifying one’s short-term rental business beyond platforms like Airbnb.

They discuss potential implications if a co-founder, Joe Gebbia, causes disruptions leading to an Airbnb downfall. Mike emphasizes the critical need for establishing direct booking systems, collecting email lists, and leveraging social media to build a s...

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In this episode of 'The Hideaway Show: Behind the Curtain,' hosts Jordan Holmes and Mike Sebastian return to discuss their journey in 2024 and their ambitious plans for 2025. They dive into their experiences and the lessons they learned last year, focusing on the importance of social media for bookings and the value of on-site management.

The hosts are excited about their upcoming unique projects, including innovative, unique build...

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In this episode of The Hideaway Show, host Jordan Holmes speaks with Dustin Baker, the owner and founder of Hidden Gem Media. They discuss the importance of branding and marketing for vacation rental businesses, emphasizing the need to differentiate and build trust to achieve premium pricing and higher occupancy rates. Dustin shares his journey in the marketing industry and how it led him to focus on the short-term rental sector. T...

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In this episode of the Hideaway Show, host Jordan Holmes interviews Gil Chan from Crafted Stays. They discuss the importance of nurturing guest relationships to boost direct bookings for short-term rentals (STRs). Gil shares his personal journey as a host and explains how his company helps other hosts create high-performing direct booking sites. They also cover topics such as email marketing, SEO, social media strategies, trust-bui...

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On this episode of The Hideaway Show, host Jordan Holmes sits down with Heather and Erin from Pink Wall Designs. Heather and Erin are experienced hospitality interior designers who specialize in maximizing ROI through design and brand partnership opportunities. Together, they dive deep into:

  • What virtual design entails and how it helps Pink Wall Designs stand out from other interior designers in the hospitality space
  • Why bui...
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Welcome to another episode of The Hideaways Show - Behind The Curtain. On this episode, Mike and Jordan breakdown:

  • How there are big profit opportunities in small-sized unique STR builds
  • Mike’s new 16 acre development available to investors in the Red River Gorge of Kentucky
  • Why you should focus on targeting the modern spontaneous traveler
  • How to overcome challenges and the importance of built out, robust systems

J...

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Welcome to another episode of The Hideaways Show - Behind The Curtain. On this episode, Mike and Jordan breakdown:

  • Four areas where hosts aren't investing enough time or money
  • Why unique amenities are critical to making your property even better
  • The importance of providing an extraordinary experience for each of your guests

Join our free weekly calls where we talk about how YOUR STR can stand out: https://www.buildyo...

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On this episode of The Hideaway Show, host Jordan Holmes sits down with Chase Charifa. Chase is no stranger to unique, experiential properties and has mastered how to provide a memorable stay for all his guests. Together, they dive deep into...

  • The “hidden amenity” at Lightfoot Cabin and how curiosity brings about more bookings
  • How Chase leverages lifestyle photography to attract brands to his properties
  • How Chase was able...
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Welcome to another episode of The Hideaways Show - Behind The Curtain. Today Mike and Jordan breakdown:

  • The 328% increase from focusing on your SEO and listing optimization
  • How Airbnb rewards you for being a pro-active, attentive host with your listings
  • The “levels” to the short-term rental investing game and why too many hosts are leveling up before doing the required initial steps

Join our free weekly calls where w...

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