How Hospitable.com enabled this remote rental host to go from strength to strength

Have you ever dreamed of managing a great vacation rental property, making good money and giving guests a great stay, but without you ever having to visit the place in person? 

Jason Wolohan and his wife Rachel don’t have to dream. They’re doing it. 

As successful hosts of a rental in the Smoky Mountains, Tennessee, they run their property entirely remotely from Maryland (eight hours’ drive away), without sacrificing attention to detail, great communication, or guest experience. They’ve saved time and money, and are now planning to expand.

And they do it all with Hospitable.com—our tool designed to help hosts do exactly that.

“When I talk to my friends about it, most are concerned with how long a rental would take them to manage,” says Jason. “But then I tell them about Hospitable.”

Whether you once lived near your property but moved away, or always intended to work remotely, enabling your operation to run smoothly without your presence is the holy grail of remote rentals. 

However, coordinating everything from afar can feel overwhelming (especially when you hear horror stories of lost keys, noise, or guests arriving to a dirty rental).

That’s why in this post, we’ve:

• Taken a tour of Jason and Rachel’s successful cabin in the Smoky Mountains

• Explained why they needed an automation tool in the first place

• The 7 ways Hospitable.com enabled them to run a thriving business from the start

• Shown how the time and money saved means the couple is now poised to expand their business even further without extra time or stress

Remote management: Jason’s cabin in the Smoky Mountains

Described as a “resort cabin”, the couple’s property is both luxurious and expansive, while also managing to be cozy and pleasingly rustic.

A cozy, easy stay

Just seven minutes from the Great Smoky Mountains National Park, it sleeps six, and has clearly been designed for maximum comfort and carefree vacations. The average stay is just three to seven days, so everything is designed to enable guests to arrive, and relax immediately.

There are paneled, cozy walls and deep couches, plus a fireplace for colder nights—as well as summer must-haves such as a pool, sunloungers, private hot tub, board games, BBQ grill, and outdoor rocking chairs.

The place is practical too, with fast Wi-Fi, smart TVs with Roku, a fully-stocked kitchen, tea and coffee making facilities, and easy smart lock entry via digital door code for easy, anytime access.

Having traveled to the Smoky Mountains on vacation before buying the cabin, Jason and Rachel knew the attractions of the area, and how important it was to be close to the national park, without straying too far from downtown conveniences.

Clear communication

What’s more, the cabin’s Airbnb listing is a masterclass in communication and goes a long way to show why the place has been so successful even without its owners on-site.

It clearly lists the many positives of the cabin (clean sheets, private hot tub, warm throw blankets, salt water pool, communal fire pit…) at the same time as explaining the strict rules for guests (no smoking, no pets, no parties, on pain of extra fees and request to leave).

This establishes clear, friendly-yet-firm communication upfront even before guests book, and is likely to attract guests who love the sound of the amenities and are, in return, only too happy to abide by the rules. (It is likely to deter those who are perhaps less amenable, too).

Clear communication between hosts and guests is a key benefit of using Hospitable.com. And, as a frequent Airbnb user himself, Jason is open about the amount of work the couple put in to making the property as guest-friendly as possible.

“We spent a lot of money on our property and I did a lot of research,” he says. “Even before that, well, my wife and I had been using booking platforms like Airbnb for a long time as avid travelers.”

Why the couple needed a powerful automation tool

As someone with Airbnb experience, Jason and Rachel were aware of how guests want to be treated by hosts. 

But, with a full-time job and a permanent home hours away across the country, they needed a tool that could help them to provide excellent service while still managing a vacation rental remotely.

Jason said that he knew that remote, automatic software was out there, because of (unfortunately) a bad experience when staying at a cabin the year before.

“We went to go look at the Smoky Mountains last summer because we were considering investing there, and we stayed in a cabin,” he explains. “But the host sent some things that felt robotic, which I felt like a human didn’t see.

“I could tell that he was automating these messages without them being well-written or personable. But that’s how I knew these tools were out there. I think my previous traveling experience meant I understood what I needed more quickly.”

As a result, Jason was determined to find a tool that would function much more effectively. Considerable YouTube, Facebook group, and podcast research later, he chose Hospitable.com for its robust functionality and ability to both automate and personalize.

He explains: “Rather than focusing on price or the company with the best review videos on YouTube, I tried to find videos of users who were showing how they used the actual product.

“There were some features that were really important to me, and Hospitable had most of them.”

7 ways that Hospitable.com enabled the couple to run a thriving business from the start

For a couple so determined to find the perfect automation tool for them, Jason and Rachel unsurprisingly use many of Hospitable.com’s major features to streamline their Airbnb operations, ensure happy guests, and boost revenue.

1. Messaging automation

Top of Jason’s must-have list was a powerful communication tool. He wanted something that could be set up once, send messages to guests automatically, and also answer their questions even if neither Rachel nor Jason could reply immediately.

“My biggest priority was to have complete communication automation, because I work a full-time job,” he says. “And when I say complete, I mean, I wanted to be able to send event-based messages, such as at check-in and a day later—but that’s pretty standard.

“I also wanted automatic replies. And that’s where I felt like Hospitable.com did a better job. Getting back that time [on replies] is what I was after.”

With its powerful AI technology, Hospitable can detect the content of messages and send tailored replies designed to sound like a real human, even if a real human isn’t available.

“I felt like the AI behind that was better than its competition, in terms of recognizing the questions,” says Jason. “When someone asks a question, it identifies what the question is, and it automatically answers for me. You can ask it 1,700 different ways and still tell it what you want the response to be.”

Hospitable.com also enables users to tailor messages quickly, for even more personalization.

“People think I’m really friendly,” jokes Jason. “Of course, I feel like I am, but I took the time to write those messages six months ago, and now it’s just automation. That’s the beauty of it. I can be totally hands off, because Hospitable.com sends it automatically.”

The couple’s automated message flow includes: 

• A thank you message for guests who book on Vrbo and Airbnb

• A reminder of the House Rules

• Timely offers of extra nights if the calendar is available

• A check-in reminder with the digital smart lock door code

• A friendly message to see if everything is going smoothly, the day after check-in

• Check-out reminder and instructions, tailored to the length of stay

• Review request just before check-out

2. Smart locks and check-in

A key (pun somewhat intended) part of operating a remote rental is enabling guests to arrive, check in, and check out digitally, without requiring a human (or a physical key) to be on-site to let them in. 

Instead, guests are sent a keypad code two days before check-in.

Rather than making guests’ arrival unwelcoming, operating smart lock check-in actually improves the guest experience, because they can arrive and get in whenever they like (within the house policy). 

Operating check-in digitally also means hosts can send a welcome book with local recommendations, and reiterate the House Rules for transparent communication (which Jason does). It also improves security, because the code is tailored to each new guest, and changes on check-out.

“Hospitable integrates with Schlage, so when guests book, it takes the last four digits of their phone number and makes a code for the lock, which is only good from check-in time to check-out time,” explains Jason. 

“That message is sent two days before, and includes that custom code, so they know where the lock is and what the lock code is, plus any other check-in instructions they need.”

3. Upsells and extra nights

Using an automated tool that sends timed messages has also helped the couple to boost revenue and increase occupancy, by sending guests the option to check in the day at a discounted rate.

Guests receive such a message the week before they arrive (if available), plus a 20% discount for the extra night, as well as a reminder the day before (again, if available).

Again, this is the advantage of a smart tool such as Hospitable.com automatically coordinates the message so that it is only sent if the calendar is free, to avoid double-booking. And it pays off, literally, says Jason.

“I would say right now our success rate is 30-40% for extra nights,” he says. “And it enables me to do it totally hands-off. I basically set it and forget it, as it adjusts automatically, so guests don’t get asked if they want to stay another night when they’ve barely arrived.”

4. Automatic reviews (by guests AND of guests)

When it comes to gathering positive feedback and saving the couple a ton of time, Hospitable.com helps with both. 

As part of the automated messaging flow, guests are sent check-out instructions before they leave, but also receive a friendly message thanking them for their stay and asking them for a review. 

The message also lets the guest know that they will receive a “five-star review” from the hosts too, as an extra incentive. 

“We talk about it in our messages and in our guidebook, and emphasize how important it is,” says Jason. “We say things like ‘I hope you’re having a five-star stay’, to try to make it more obvious.”

Plus, because Hospitable.com’s messaging timetable can be timed accurately, Jason purposefully alternates his messages with those from the booking platforms, ensuring that guests aren’t overwhelmed.

He explains: “I don’t send it to them on the exact day they check out, because they’ll get a message from Airbnb or Vrbo then. But the next day, I send them an automated message that says, ‘We’re going to leave you a five-star review, we would appreciate you do the same’.”

He says: “I try to time our messages in between those because I don’t want to bombard them. But it’s easy to forget. So we set it up so there’s three straight days where the guest gets a message asking them to review.”

And the method appears to be paying off. “We have about a 90% review rate, and we have all five stars so far,” says Jason.

It also saves him hours of time in manually typing out reviews, as Hospitable.com can also be set up to review guests automatically.

5. Team and task coordination

And when guests check out, the automation continues, meaning the couple doesn’t even have to visit the property in between bookings.

Hospitable.com’s Task Management and Team Collaboration features mean that they can coordinate cleaning and maintenance at a distance-even in the event of last-minute bookings, early arrivals, or late check-outs.

“The ability to kind of have a team was another feature we were looking for,” explains Jason. “We don’t have a payroll, but we do have a cleaner and a handyman; people that help us manage. And Hospitable.com gives you two methods to communicate with those people, email and texts.”

As hosts, Jason and Rachel are sent a message whenever they get a booking, as is the cleaner. It also sends thank you messages after the cleaning is complete.

Hospitable.com also allows for easy coordination, because “you can give your cleaner or anybody else on your team access to your calendar”, explains Jason. “That was important to us.”

Not only does this help streamline check-outs and check-ins, and ensures that the space is always ready for new guests, it also saves Jason even more time. 

“I didn’t want to sit down at the beginning of a month, or any time really, and have to write out all those details to send them to our cleaner,” he says. “I wanted them to just be able to log in on their own.” 

Plus, the system is adaptable and specifically designed for team access.

“It’s great that you can assign levels of access, so our cleaner can literally just see the calendar,” says Jason. “They can’t see anything else, such as guest messaging, or how much everyone is getting paid. They can only see what they need to for their job, which was important for us, too.”

6. Dynamic pricing

A marker of a successful rental is good revenue and competitive rates, and Hospitable.com helps with that too, so Jason and Rachel don’t have to keep constant track of the Smoky Mountain market manually.

Because Hospitable.com integrates with the dynamic pricing tool PriceLabs, it adjusts the rental’s nightly rates on connected booking platforms according to season, local events, occupancy, demand, and a host of other sensitive insights.

It also enables hosts to adjust their rates depending on the given OTA’s fees, so the host doesn’t have to miss out on the difference each time.

“What I like about Hospitable.com is that you have the option to add a premium,” explains Jason. “I know that Vrbo or Airbnb will take, say, 3% to 8%. So Hospitable enables me to add a little to make up some of that.”

7. Potential direct booking capability

Jason also enjoys how Hospitable.com is always adding more features that help hosts make more money.

Currently, he is applying his trademark attention to detail to consider how to use Hospitable’s forthcoming Direct booking website feature, which would allow the couple to sidestep OTA fees entirely, saving money, and reducing reliance on booking platforms and their constantly-changing algorithms.

“The other thing that was important to us was a direct booking capability,” Jason explains. “Hospitable didn’t offer this when we started, but I was confident that they were building pretty fast.

“I’m aiming to get to a place where at least 20% of my bookings for the year are direct bookings,” he explains. “Because then I know that I’ll be able to cover my costs, even if Airbnb or Vrbo decided they don’t like my place or don’t want it on their platform anymore, for whatever reason.”

He is also looking more closely at its financial and operational tools, and awaiting more soon.

“One of the things I’m waiting for is an integration with my tax tool, so I can use it to see what I owe for taxes,” he explains. “Once Hospitable has that, I feel like it will check the boxes of any channel manager.”

Hours saved

Jason estimates that between the automated messaging, team management, AI question responses, and calendar booking management, Hospitable.com saves him around five hours per week, or 20 hours per month. 

“I did spend quite a few hours up front. But after that, you know, you get your return on time back pretty quickly,” he says.

Hospitable.com even tells you how much time each automated message saves, leaving him free to work elsewhere, and spend more time with his kids. “If I click on an automated message, it tells me that it’s going to save me nine minutes,” Jason explains. 

“If you figure that I’ll be watching my kid ride his bike outside, and then all of a sudden, I would have to remember, ‘Oh yeah, I need to send a check-in message, or a check-up message to those guests who checked in yesterday’…well, nine minutes seems pretty reasonable,” he says.

He calculates that compared to manually setting a reminder, pulling out his phone, typing a message out, and then hitting send, the estimate is “pretty accurate”. And the time saved is multiplied with each guest, adding up to hours a week.

“It’s a very good feeling of peace of mind knowing that I don’t have to dedicate the mental capacity to managing some of these items daily,” he says.

Major growth potential unlocked

With this money and time saved, plus the consistent revenue that comes from a successful rental, Jason and Rachel are now planning to expand their business throughout the US, at a rate of around two new properties per year for the next five years.

And again, they plan to use Hospitable.com to manage this growing portfolio entirely remotely, meaning he will be free to invest in short-term rentals without adding more hours to his workload.

“We’re putting in offers in Florida now,” he says. “We want to pick places that we would vacation ourselves, because we find it more fun that way.”

And because Hospitable.com is designed to work across multiple properties, Jason is confident that he can expand his existing time-saving processes easily. He has even started preparing the software for expansion ahead of time.

“I’ve already noticed it,” he says. “A lot of the messages allow you to select whether you want to send that message to all of your properties or just one of your properties. 

“So if you have a message that only applies to Florida, such as a local market recommendation, you can set it up to only send to that specific property. 

“I’ve already started building that in,“ he says. “Selecting messages to only send to one property. I can’t see that being an issue whether I have two properties or 10. It allows that flexibility. I don’t foresee any issues with that.”

Remote rentals: From Smoky Mountains to success

From the super-communicative Airbnb listing to the automated request for a good review, Jason has proven how an automation tool such as Hospitable.com can enable efficient rental management entirely remotely.

And harnessing the power of Hospitable.com’s features has enabled Jason and Rachel to go from strength to strength, investing the time and money saved into nationwide expansion plans. 

With Hospitable.com on his side, Jason’s sights are as high as the Great Smoky Mountains and beyond—and the view looks just as clear.