STR Investing, The Podcast

In this week's Monday Market Data Report, Mark Lumpkin breaks down one of the most requested short-term rental markets in the country: Destin, Florida. With more than 8 million annual visitors across the Destin and Fort Walton Beach area, this Emerald Coast destination continues to be one of the strongest beach markets for STR investors. In this episode, Mark covers: Revenue potential by bedr...

AI is changing the way travelers discover short-term rentals—and it’s happening faster than most hosts realize. In this episode, Mark Lumpkin sits down with Gil Chan, Founder & CEO of Crafted Stays, to discuss how AI search, direct bookings, and modern website strategies are reshaping the future of the STR industry. Gil explains why relying solely on OTAs is becoming increasingly risky, how AI...

In this week's Monday Market Data Report, Mark Lumpkin breaks down the short-term rental market in Asheville, North Carolina, combining revenue by bedroom count with amenity data to show investors exactly where the biggest opportunities are. Despite the challenges following Hurricane Helene, Asheville continues to be one of the country's fastest-growing mountain destinations, welcoming m...

Most short-term rental owners assume Airbnb and Vrbo handle all of their lodging taxes. They don't. In this episode, Mark Lumpkin sits down with Julie Banting Rogers from Avalara to uncover one of the biggest blind spots in the STR industry: lodging tax compliance. Julie explains why thousands of hosts and property managers unknowingly fall out of compliance, how platform-collected taxes actu...

In this week's Monday Market Data Report, Mark Lumpkin breaks down the short-term rental market in West Palm Beach, Florida, combining bedroom-count revenue data with amenity-stack analysis to show investors exactly where the biggest opportunities exist. West Palm continues to see strong tourism growth, with more than 10 million annual visitors and growing demand fueled by major corporate rel...

What does it take to stay relevant in the short-term rental industry for nearly three decades? In this episode, Mark Lumpkin sits down with Michael St. Pierre, a hospitality veteran with 28 years of experience spanning vacation rentals, luxury resorts, revenue management, owner acquisition, and some of the industry's most recognized brands. Michael shares how he got started in the business, t...

In this week's Monday Market Data Report, Mark Lumpkin breaks down one of the most competitive short-term rental markets in America: Sevierville. With more than 15 million annual visitors to the Great Smoky Mountains and over 13,000 active short-term rentals in the surrounding market, Sevierville has become the perfect example of the "Amenities Arms Race" that has transformed the ST...

Tax season just got a lot more interesting. In this episode, Mark Lumpkin sits down with CPA and real estate tax strategist Ryan Carriere to break down one of the most powerful tax strategies available to short-term rental investors today. Ryan explains how the return of 100% bonus depreciation under the One Big Beautiful Bill impacts investors, why the Short-Term Rental Tax Loophole remains a gam...

In this week’s Monday Market Data Report, Mark Lumpkin heads to the Pacific Northwest to break down the short-term rental market in Seattle, Washington. With more than 5,000 active listings, nearly 40 million annual visitors, and inventory growth exceeding 50% over the past few years, Seattle has become an increasingly competitive market for STR investors. But despite the growing competition, the...

A dirty property can ruin a guest experience before the vacation even begins. In this episode, Mark sits down with Logan, founder of Dream Clean Team, one of the largest vacation rental cleaning companies on Florida's Emerald Coast. Starting as a side hustle with his wife cleaning properties during summer break, Logan has grown the business into a full-service operation serving hundreds of sh...

Yosemite is one of the most visited national parks in America, attracting more than 4 million visitors every year. But when it comes to short-term rentals, the opportunity may be even bigger than most investors realize.  In this week’s Monday Market Data Report, Mark Lumpkin breaks down the Yosemite STR market, including travel demand, regulations, seasonality, and the amenities that separate aver...

AI is moving faster than most short-term rental hosts realize. In this episode of the STR Investing Podcast, Mark Lumpkin welcomes back Boostly founder Mark Simpson for a deep dive into how AI agents, automation, and direct booking technology are changing the future of hospitality. Mark Simpson shares how he went all-in on AI at the beginning of 2026, replacing repetitive manual tasks with AI agen...

Mark Lumpkin breaks down the short-term rental market in Galveston — one of the fastest-growing and most competitive beach markets on the Gulf Coast. With over 6,000 active listings and supply up more than 50% in just two years, Galveston has become a major target for STR investors. But despite the competition, there’s still a clear path to winning. In this episode, Mark covers:  The travel demand...

What happens when a short-term rental operator loses over $1,000,000 during COVID? In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Jason Baxter to talk about the highs, lows, and future of the short-term rental industry. Jason shares how he accidentally got started in Airbnb over 10 years ago, scaled to a portfolio of 50 lofts in Montreal, and then watched everything coll...

Mark Lumpkin breaks down the short-term rental market in Charleston — one of the most desirable and tightly regulated STR markets in the Southeast. Charleston is a heavyweight market:  Over 8 million annual visitors  More than $14 billion in tourism impact  Strong ADRs and occupancy   And some of the strictest STR regulations in the country  In this episode, Mark dives into:  Why Charleston contin...

Smart locks are no longer optional in short-term rentals. In this episode, Mark Lumpkin sits down with Amber Baron from Dormakaba to talk about why access control is one of the most overlooked parts of the guest experience — and how bad systems can completely ruin a stay. They break down: Why check-in is one of the most important moments in hospitality The biggest mistakes hosts still make with pr...

Chattanooga might be one of the biggest STR opportunities flying under the radar. In this week’s Monday Market Data Report, Mark Lumpkin breaks down why Chattanooga is still in the early innings of the amenity arms race — and how investors can create a true “unicorn” property with surprisingly little competition. The numbers are eye-opening: Only 18% of listings have hot tubs Only 3.8% have swimmi...

AI is changing business faster than ever — and short-term rentals are no exception. Mark Lumpkin sits down with Nick Korwin to talk about building a luxury micro resort from the ground up while working full-time in the AI and autonomous vehicle industry. Nick shares: How he transitioned from traditional rentals into short-term rentals Why he chose to build a micro resort instead of buying more hou...

STR software is evolving fast - but the best operators know the real edge isn’t just automation. In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Amber Knight from bookingcloud.com to break down where the industry is headed—and what most hosts are still getting wrong. Amber shares her journey from helping scale early-stage operations at Vacasa to building new technology th...

In this week’s Monday Market Data Report, Mark Lumpkin breaks down the short-term rental data for Scottsdale and the greater Phoenix market — and answers the big question: Is it actually oversaturated? Using real data and strategy from STR Search, this episode shows why Scottsdale is still one of the most opportunity-rich STR markets in the country — if you know how to play it. Inside the episode:...

What if your next investment wasn’t a house… but something on wheels? In this episode, Mark Lumpkin sits down with Gar Russell, founder of Fireside RV Rental, to break down an entirely different angle on hospitality investing. Gar shares how he went from building and losing a multi-million dollar real estate portfolio… to creating the largest RV rental management franchise in the country.  They di...

In this week’s Monday Market Data Report, Mark Lumpkin breaks down the short-term rental data for Big Bear Lake — including a full market snapshot + amenity performance breakdown. This episode introduces a new format, giving you a clearer picture of:  Overall market supply and demand   Where guests are coming from   Seasonality and booking patterns   And which amenities actually drive revenue  Her...

In this week’s Monday Market Data Report, Mark Lumpkin breaks down the amenity data for The Poconos — one of the most competitive and heavily amenitized STR markets in the country. This episode reveals a massive truth about the Poconos: Amenities aren’t optional. They’re everything. Using data from STR Search, we break down what top-performing properties are doing differently — and why some homes...

In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Pierre-Camille Hamana, founder and CEO of Hospitable, to break down how short-term rental software has evolved over the last decade and where the industry is heading next. Pierre shares how he went from hosting a single room in Brussels to building one of the most recognized property management platforms in the space. They d...

In this episode, co-host Taylor Jones breaks down a simple, practical framework for building your short-term rental buy box without needing expensive tools or large amounts of capital. If you’ve ever asked yourself where to buy, what to buy, and how to know if a deal actually works, this episode walks you through it step by step. Taylor explains how to use Airbnb itself to identify top-performing...