What Happens When Hotels & Airbnb Merge?

Are hotels and short-term rentals starting to blend? Orlie Benjamin thinks so — and she breaks it down in this insightful episode of the Host Planet Podcast.



Transcript

00:00 – Cold Open

Orlie Benjamin: Fifty percent of the joy from a vacation happens with the anticipation of the vacation. You don’t say, “I have vacation rentals” — you say, “I have Airbnbs.” Airbnb has taken everyone’s branding and made it theirs. I think hotels and vacation rentals are competing for the same customer.

James (Host Planet): Are hotels and short-term rentals blending into one business? And what can vacation rental managers learn from the hotel industry, especially when it comes to guest experience, branding, and upselling? Orlie Benjamin previously worked for NetJets, Victoria’s Secret, and American Airlines, and her new solution could be about to bridge the gap between hotels and short-term rentals, helping serious hosts and property managers supercharge their businesses. Tune in to learn more on today’s Host Planet podcast.

00:58 – Why Hotels and Vacation Rentals Are Blending

James: Orlie, why do you think hotels and short-term rentals are blending?

Orlie Benjamin: It really comes down to customer behavior. Traditionally, when people wanted to go on vacation, they looked at hotels. Airbnb democratizing access to home rentals changed the game, even though the industry itself has actually existed much longer than Airbnb.

When you look at how different customer segments travel, a lot of millennial families would rather have more space and more amenities — especially a family of two adults and two or three kids — versus being crammed into adjacent hotel rooms, with amenities downstairs they can’t really use once the kids are asleep. Thinking about how families actually travel, and what they value — a great experience for both kids and adults, plus price and convenience — vacation rentals have disrupted the travel model by offering that trade-off. Maybe you don’t get your room cleaned every day, but you gain a lot in return, and that applies to groups of friends just as much as families.

James: What do you think short-term rental operators can learn from hotels? Everything you’ve said makes sense, but there are still plenty of people who prefer hotels.

02:22 – What Hotels Still Do Better

Orlie Benjamin: It comes down to guests and what they value when they travel. For some travelers — say, a couple who just need a place to sleep and spend most of their time out in the city or at restaurants — a hotel makes complete sense, because the conveniences and amenities are all there and the group is small, so they don’t need to spend much time in the room.

But for larger groups traveling together, the hospitality element that hotels bring is still often lacking in the vacation rental experience. I’ve worked for some great hospitality brands, and as someone who loves to travel, I’ve experienced that hospitality personally as a guest too. There’s real value in feeling anticipated when you arrive somewhere — that’s almost the definition of hospitality: feeling welcome, known, and comfortable.

In a vacation rental model, it can be very hard for an operator — especially a remote one, which most are — with no one on site, to create that feeling. Hospitality is, in a lot of ways, an emotional exchange: one person gives, another receives. Hotels have people physically on site to create that experience; it’s much harder to build human connection remotely. I think there’s a lot of room for vacation rental managers to extend hospitality remotely in ways that haven’t yet become standard practice across the industry. It’s genuinely white space, and a real opportunity.

James: So what can they actually do? What’s the next step for remote hosts who are struggling to create that human connection?

04:39 – Turning Hospitality Into People, Process, and Systems

Orlie Benjamin: Everything in business ultimately comes down to people, systems, and processes. What Lasoh does — the business I founded — is bring the systems component to that. But before I talk about my business specifically, let me back up a couple of steps.

First, hospitality has to actually be a value of the business. Whoever runs the business has to decide, “Hospitality is part of our value proposition,” and that has to come from the top down. It’s a legitimate choice not to prioritize it — some vacation rental management companies simply don’t invest time and resources into hospitality as a value. But if a business makes the strategic decision that they want guests to feel seen, welcomed, and want them coming back and telling friends, they’ll invest the extra effort to make that happen.

Once that value is established, it becomes a matter of organizing the business around it. There’s a people element — whose role is it, and how do they fit into the guest journey? There’s a process element — how do you build that into something repeatable and low-lift, so people aren’t overburdened by unreasonable demands? And then there’s the systems element — the technology that enables those processes, some manual and reactive, and some proactive, using tech to create a feeling of hospitality without requiring a human to intervene every single time.

A good example of how hotels — or even other travel businesses — do this is automated messaging tied to the customer journey. At NetJets, for anyone who doesn’t know, a private jet company, one of the most important things we did was mapping the customer’s journey and knowing exactly where they were in it — from the moment they booked a trip, which could be hours or months before departure, all the way to boarding. That journey has specific milestones, and proactive messaging that anticipates someone’s needs at each milestone is a way to bring hospitality into the experience through technology, without requiring a human at every single touchpoint. Of course, at the NetJets level, there are humans at every moment too, in addition to technology, because it’s arguably one of the highest levels of luxury hospitality in the world.

What Lasoh does is enable vacation rental managers to automate and proactively anticipate the guest experience, setting up guest journeys with automations that ensure a great experience starting from the moment of booking — not the moment of arrival. The vacation actually starts as soon as you book it. There’s research showing that 50% of the joy of a vacation comes from the anticipation leading up to it. If you’ve ever taken a super last-minute trip and felt like something was missing, that’s why — there’s something deeply energizing for humans about having something to look forward to.

Lasoh does this in a variety of ways I won’t fully unpack here, but that’s the framework for thinking about bringing hospitality into vacation rentals.

08:03 – What Hotels Get Right About Data and Upsells

James: A few things hotels do really well are understanding how important it is to capture guest details, even when someone books through Booking.com or Expedia, and they’re incredibly good at upselling — spa, restaurant reservations, activities. How can vacation rental owners apply what hotels do in those areas?

Orlie Benjamin: This might sound like a plug for Lasoh — I’ll get to that — but fundamentally it comes down to knowing who the guest is from the moment of booking: what kind of trip they’re taking, who they’re traveling with, and what the trip is actually about. From that understanding, you can offer the right recommendations to make their trip great, and start the revenue-maximization process from the point of booking in a way that genuinely adds value for the guest.

Revenue is a multiple of three things: how much each guest spends per trip, how many trips each guest takes over time, and how many guests you have. Multiply those together and you get revenue, and there are levers in each of those areas — early check-in, last-minute upgrades, in-room dining, and so on, the same tools airlines and hotels have always used. It comes back to understanding the needs and wants of the guest and anticipating them in a way that maximizes revenue. First, you have to know who they are. Second, you have to be able to reach them. Third, you have to be able to do it in a way that’s automated and effective.

There are a lot of point solutions in this space handling pieces of this, but nothing comprehensive, and what’s really missing is genuinely knowing the guest — because you can throw offers at people, but if they completely miss the mark, it feels irrelevant and actually detracts from the experience rather than adding to it. What Lasoh has built is infrastructure to understand who the guest is from the point of booking, giving them a better experience through a digital portal — similar to a Marriott app, or honestly what NetJets has internally. That portal becomes the source of truth for communication, trip recommendations, and revenue maximization, whether that’s upgrading a fare, adding something to a hotel stay, or booking an excursion.

Concierge service is actually something I think is underutilized for revenue maximization too. There’s the value of lodging, and then there’s the value of the whole trip — lodging is typically only about a third of what someone spends on vacation. If you can naturally insert yourself into the rest of that spend — food, excursions, some element of travel — that’s how you maximize revenue: thinking about the whole stay, and providing enough value that the guest chooses to spend through you.

11:12 – Sponsor Break: HostHub

James: HostHub is a top-rated property management platform for short-term rentals. HostHub can help you increase revenue, improve operations, and ultimately save you time and money. It has everything you need to manage your properties effortlessly and reliably — syncing rates and availability across every channel your properties are listed on, plus automated messaging, team management, and expense tracking. It also includes smart pricing integration, task and cleaning management, and automated door locks.

HostHub offers a zero double-booking guarantee, 24/7 support with an average response time under three minutes, and a clean, friendly interface that’s easy to learn and use. Right now, HostHub is offering a 14-day free trial to any host or property manager who wants to try the platform — head to hosthub.com/hpp for details.

11:37 – The Risk of Over-Upselling

James: I booked a flight with a budget airline a couple of weeks ago, and it was similar to what you’re describing — they wanted to sell me insurance, car hire, a hotel room, an excursion, everything, and I just kept clicking “no, no, no.” You’ve got to be careful not to make it an annoying guest experience.

Orlie Benjamin: I completely agree, and that’s part of why knowing the guest matters — so what’s offered actually feels relevant. Timing matters too. Airlines tend to cram everything into the initial e-commerce funnel, with almost no follow-up between booking and departure. That’s not the only way to do it — it’s just the way it’s always been done, and I’d actually argue it’s not the smartest approach. If an airline knows who someone is, they could communicate meaningfully between booking and departure based on the traveler or the trip, and serving the right recommendation through an app or a well-timed follow-up message could actually convert better than front-loading everything.

Coming from an e-commerce background, you have to be very careful about people falling out of the shopping funnel. Push too much before the point of purchase and you risk losing the sale entirely; push too much after, and people simply abandon the journey. All of that is trackable — it’s just a matter of someone actually measuring it and optimizing through A/B testing. Airlines have probably just kept doing things the way they’ve always done them, because relative to their other priorities, this may not be the thing they’re most focused on fixing.

James: Right — once you’ve paid for your bag, you really don’t want to pay for anything else. That’s certainly been my experience with airlines.

14:44 – Where Point Solutions Like Gated Wi-Fi Fall Short

James: There are a lot of upselling platforms in this space right now — seems like a new one every week — along with things like gated Wi-Fi solutions that gather guest data to help hosts earn upsell revenue. Where do you think these tools are falling short, and what convinced you there’s a real gap here?

Orlie Benjamin: I think they’re point solutions addressing one narrow moment in the journey, and a truly great hospitality business thinks about the whole journey, not just a single point in it. Relationship marketing, by definition, is the idea that someone is your customer, and you re-engage with them at any point to drive revenue or another action.

Something like holding internet access hostage as a marketing tactic is almost a direct contradiction of relationship marketing. If the first thing a guest experiences when they walk into a home and try to connect to Wi-Fi is being asked for their information before they can get online, that’s not going to make them want your brand in their inbox — it’s a negative experience, with nothing relationship-building about it at all. It’s a very old approach hotels used decades ago, partly for legitimate reasons back then, like conserving bandwidth, since internet access used to be genuinely expensive. But the world’s changed — internet is far cheaper now, so that cost-saving rationale mostly doesn’t apply anymore. As a relationship-marketing tactic, it feels outdated, and honestly not even in the spirit of relationship marketing at all.

As for upsell platforms generally, there’s real logic to them — it comes back to the idea that lodging is only a fraction of total vacation spend, so capturing more of the overall stay makes sense. But I think upselling in a minimal, narrow context is much harder to convert well, and it’s also hard to defend as a standalone point solution, because eventually every PMS builds that functionality in-house — several already have. Any software focused purely on upsells will likely see some early success, but it becomes indefensible once PMS platforms absorb that functionality natively.

The bigger opportunity is the overall relationship with the guest and the ability to build brand loyalty — because ultimately, brands carry real value. I actually used to run licensing for a large CPG company, and the licensing business model illustrates this well: anyone can buy a white-label version of a product at a grocery store — take milk, for example. There might be a local-farm brand, a nationally recognized brand, or the store’s own private label. The premium people pay for an established brand runs anywhere from 10 to 20%, depending on the category. What a brand really is, is a promise — that certain standards will be set and met. That’s a huge part of hospitality. So point solutions around upsells can drive some revenue, but they’re short-sighted if they’re not considered within that larger brand ecosystem.

18:44 – Why Every Vacation Rental Needs a Brand

James: Is that where you see the industry heading — property management companies developing their own brands? And does that apply to people lower down the food chain, with just one or two properties? What would you say to someone thinking, “I’ve only got one rental — do I really need a brand? Will it actually help me that much?”

Orlie Benjamin: I do think everyone should have a brand, because a brand is simply a promise plus the delivery of that promise. Even something like “Grandpa Joe’s Cottages” — Grandpa Joe is part of that brand. It’s the promise of the effort he puts into curating experiences for his guests, and that’s exactly what people recognize when it’s exceptional — it’s what earns referrals, repeat visits, and positive reviews.

The irony is that Airbnb has actually become the brand for everyone else’s business. If someone owns, operates, or manages a handful of units, regardless of the business model, they don’t say “I have vacation rentals” — they say “I have Airbnbs.” Airbnb, as a marketplace, has effectively absorbed everyone else’s branding into its own.

And it doesn’t matter what price point you’re at. Walmart is a great example of a brand whose entire value proposition rests on low prices — that’s the promise, and it comes with a specific operating model: fewer staff, more self-service, a less elevated experience. If cost savings is what a customer values most, that’s a trade-off they’re happy to make. On the opposite end, think about Ritz-Carlton, or Marriott, which actually owns Ritz-Carlton. Each brand in Marriott’s portfolio makes a distinct promise, because they’re targeting different customers with different value propositions. Someone staying at an EDITION hotel probably values design, modern amenities, minimalism, cutting-edge cocktails. Someone at a Westin might prefer a more traditional aesthetic and dining style. At the end of the day, it’s not just lodging — it’s an experience, and Marriott has built a portfolio of brands that align to how different people want to travel, so guests can pick the one that fits them.

I think every vacation rental should have a brand — not just to make guests happy, but because it’s genuinely good business. Going back to the licensing point: brands exist, and the world isn’t all private labels, because there’s a real premium you can charge once you’ve established recognition and a track record of delivering on your promise. People rely on that. If someone’s on a road trip and wants coffee, and sees a local coffee shop next to a Starbucks, most people will walk into the Starbucks — not because the coffee is objectively better, because honestly it isn’t — but because the bathroom will be clean and the order will be consistent. People generally don’t want to gamble on the unknown, and branding helps mitigate that risk from the guest’s perspective.

James: And yeah, your point about Airbnb — nobody says they’re staying at a Booking.com or a Vrbo. They’re staying at “an Airbnb.” It’s remarkable how it’s become both a noun and a verb — phenomenal branding, honestly.

23:18 – Where the Industry Is Headed, and How AI Fits In

James: Looking ahead, where do you see things going for short-term rentals over the next five to ten years? And how do you think AI might change not just this industry, but the world more broadly?

Orlie Benjamin: That’s really three questions — I’ll start with where I see things going, then get to AI, though honestly I have no real idea how AI is going to change the world, because none of us do yet; it’ll come down to user adoption. But I do have a point of view on the industry.

We’re already seeing this play out. Marriott just bought a vacation rental business called Getaway for $120 million, on top of their existing Marriott Homes and Villas distribution channel. Marriott has clearly recognized that vacation rentals are a real substitute for hotel stays, and to stay relevant in market share, they need to play in that space — and they already have. Marriott is generally an early adopter as a business: cutting-edge, fast-moving, well-infrastructured, and their stock performance reflects that relative to some other hotel companies.

I think hotels and vacation rentals are increasingly competing for the same customer, and market share is fracturing depending on who that customer is, who they’re traveling with, and why. Business travelers still skew heavily toward hotels because of loyalty programs, points, and status. Loyalty in this space more broadly is clearly coming — I’m blanking on the name, but the founder behind The Points Guy has started a loyalty-based system aimed at vacation rentals and boutique hotels, and that’s already entering the industry.

Brands genuinely exist in this space already, and you can see that some of the highest-occupancy properties are the ones with real brand recognition and hype around them. And the definition of “experience” is incredibly open-ended right now. Vacation rentals have actually raised the bar for hotels — now hotels are adding pickleball courts, and in some cases lowering the bar in other ways depending on their value proposition. I stayed at a nice hotel in Miami recently where they don’t clean the room daily as a standard practice, because vacation rentals removed that as an expected cost, and it wasn’t a fully staffed, always-on-site experience either — this “ghost hotel” concept is emerging too. Everything is blending. If you lined up thirty attributes of a hotel against thirty attributes of a vacation rental, you’d see it’s not a clean two-sided split anymore — there’s a lot of overlap and combination happening. I think the playbook for both hoteliers and vacation rental operators is going to keep shifting as those strategies blend.

As for AI — it’s incredibly disruptive, because personalization, marketing, and guest experience have traditionally required structured data, and building a place for structured data to live, and a process for people to actually input, update, and groom that data, is genuinely hard. Even at NetJets, I saw scenarios where someone noted a guest needed a car seat, and ten years later that note was still sitting there — except the “kid” was now thirteen, not three, and clearly didn’t need a car seat anymore. The structured data existed and the process existed, but there was no real ongoing grooming methodology.

That’s exactly where AI can disrupt the process, because it can read, digest, and recommend — you don’t need the same heavy infrastructure and manual grooming process anymore. It makes personalization far better, and it raises the bar overall. I think businesses that embrace AI and personalization as part of their value proposition will see real returns, and the ones that don’t will get left behind with a commodity product that doesn’t match the expectations early-mover businesses have already set.

28:16 – What Lasoh Actually Is

James: We’ve got a lot to look forward to. Before we get to our closing questions, tell us more about what you’re working on — tell us about Lasoh.

Orlie Benjamin: Lasoh is really a combination of everything I’ve done across my career, built into software. I worked in pricing strategy at American Airlines, marketing strategy at Victoria’s Secret, and experience strategy at NetJets. I’ve also spent time in licensing and brand management at a CPG company called Scotts Miracle-Gro, and in corporate venture capital.

When I first got into vacation rentals, it was really just a personal side project — I built a cabin in the woods, bought land with room to expand — and I quickly realized there was a major gap in marketing and guest experience technology for this industry. When I looked for what I expected to already exist, I couldn’t find it, so I built it myself.

Lasoh is essentially a digital experience portal that gives guests a seamless journey, but it’s also very much an e-commerce platform, because that same portal serves as the source of truth for everything related to the trip — and it’s also where all the upselling, personalization, remarketing, and guest understanding happen. It’s a digital ecosystem that builds a real understanding of the guest, partly through host engagement and partly through the software itself.

The combination of all of that enables hosts to own the relationship with their guests, because they have data on the whole traveling group — not just the person who booked — combined with AI to understand who those guests actually are, revenue maximization through a variety of point solutions including upsells, and a remarketing engine that turns guests into your own sales force: they leave referrals, write reviews, generate social proof, tell their friends, and come back themselves. It’s fundamentally built around the entire guest journey — from booking, to spending, to coming back and telling others — as a complete, full-stack marketing engine.

James: Superb. And where can people find out more?

Orlie Benjamin: My website is Lasoh.io — spelled L-A-S-S-O-H dot io, because apparently nothing can be spelled the normal way anymore if you’re trying to buy a domain these days. I’m also on LinkedIn under my name, Orlie, and I’m sure there’ll be a link shared after this call. I’d genuinely love for anyone to reach out — question me, push my thinking, I love a good intellectual debate. If you’re curious to learn more, I’d love to talk to anyone listening to this.

James: We’ll include your LinkedIn profile and the Lasoh website in the show notes so people can find it easily.

31:29 – Sponsor Break: Zeal

James: Zeal works with holiday let owners across the UK, helping them pay the right amount of tax and not a penny more. Zeal’s team unlocks tax savings for holiday let owners on the purchase, refurbishment, and construction of holiday let properties. Their experts also advise on a wide range of tax matters, including VAT, stamp duty, business rates, and capital gains tax. Call 01632 878 98 or email hello@gozeal.co.uk to get in touch, or visit gozeal.co.uk for further details.

32:29 – Closing Questions: Favorite STR Brand

James: Okay, we’ve got a few closing questions. First — your favorite brand in the STR industry, and why?

Orlie Benjamin: I’ll actually say Marriott. Some people might not classify them as STR, but they just bought Getaway, so I think they count. As a business, from a strategy perspective, they genuinely understand the value of being customer-first and working backward from the customer to build great experiences. They also understand the value of a returning customer, and they’ve built arguably the best loyalty program in the industry.

They’re going to really disrupt vacation rental management, because as they become more of a distribution channel for vacation rental managers, operators who don’t build direct booking capability and own their book of business are essentially just going to be trading Airbnb for Marriott. I think that’s a smart move on Marriott’s part. And frankly, for vacation rental managers who aren’t focused on owning their book of business anyway, having another strong distribution competitor is a good thing — more places for guests to find properties means less leverage concentrated in any single marketplace, which is healthier for the whole industry than an overly consolidated distribution model.

James: Great shout-out to Marriott Homes and Villas there.

34:08 – Closing Questions: An Individual to Recognize

James: Next — someone in the STR industry you’d like to give a shout-out to, and why?

Orlie Benjamin: I’ve recently been talking to Rachel Alday, and I think her vision for concierge service goes well beyond what current technology can support. I love anyone with an unreasonable passion for hospitality and creating great guest experiences, who also understands how to build a real business around it. She’s dealing with unique pain points — she operates out of Utah, in the Rockies, with a business called Abode, managing about 60 units, particularly in the ski rental market, where customers have a high propensity to return and there’s real opportunity to maximize revenue across the whole trip, not just lodging. None of the systems she currently uses actually help her accomplish what she needs. I love hearing about people’s genuine pain points, because that’s always an opportunity to solve something real — anyone who’s frustrated because they want to do more than their current tools allow is exactly the kind of person worth connecting with to imagine a better future together.

James: Great shout-out to Rachel. I liked that phrase you used — “unreasonable passion” for hospitality. Very good.

35:39 – Closing Questions: Biggest Lesson Learned

James: Finally — your number one lesson learned from starting a business in the STR space?

Orlie Benjamin: I want to answer this a couple of ways. Specifically about the hospitality space — people here are genuinely friendly. I’ve worked in a variety of industries, including fashion, and people are not nearly as friendly in fashion. It’s actually made starting a business in this industry really pleasant, because I think by nature, anyone drawn to managing vacation rentals has some element of hospitality in their heart — they want to help others. When I meet people in this space for the first time, I always feel welcomed and genuinely attended to in the conversation.

I also personally have a strong sense of hospitality, in both my personal and professional life, so there’s a real kindred-spirit quality to this space that feels unique compared to other industries. In some other industries, people simply can’t be bothered — they’re focused narrowly on their own thing, with little interest in engaging with strangers, little curiosity or open-mindedness, a lot of the qualities that people who love to travel tend to have naturally. I think that genuinely makes this a great industry to be part of, because the curiosity, kindness, and hospitality that come from other people in this space create a really pleasant, high-energy environment, compared to industries where things can feel a lot less pleasant.

James: It makes sense, but it’s still a real lesson — humanity just shows up differently in different places. I completely agree — after ten years in a very corporate environment, joining the STR space has genuinely been a breath of fresh air.

Orlie, it’s been a real pleasure getting your take on the industry and learning more about Lasoh. Thanks so much for joining us on the Host Planet podcast.

Orlie Benjamin: Thank you so much, James. I really appreciate you having me, and I appreciate your time.

37:47 – Outro

James: I hope you enjoyed that interview with Orlie Benjamin from Lasoh. Building a brand and owning the relationship with your guests has never been more important. If you’re looking for more free education from the STR space, head to hostplanet.com/club, the fastest-growing multimedia platform in the short-term rentals industry. We’re proud to help hosts and property managers supercharge their businesses by sharing a wealth of free content. Head online to sign up for our newsletter, download our suite of ebooks, and listen to our podcast series. Until next time, happy hosting.