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The Playbook

Short-Term Rentals

Judy Dutton

theplaybookmb.com

This summer’s hottest vacation isn’t a party house on the beach, but the quiet solitude of a convent or monastery. Airbnb has noticed an uptick in religious retreats, particularly among Gen Z, embracing the TikTok trend of taking a summer “vow of silence.” What better place is there to quietly contemplate the Meaning of It All than a church pew?

Still, renovating a house of worship into a vacation-worthy rental can take divine amounts of patience and work to do right. Here’s how rookie real estate investor Krista Crawley ended up converting Maine’s 

 into her first Airbnb, and what she learned along the way. 

“We live in Virginia, right outside of Washington, DC. During Covid, I decided to take my kids on a road trip up to Maine for whale-watching, but the tour was unexpectedly canceled. We decided instead to spend the day at Acadia National Park, and that detour led us to Bar Harbor. We fell in love with the area instantly. On a whim, we started browsing local real estate listings and stumbled upon St. Edward’s Convent, famously known as the former residence of St. Katharine Drexel—the second American-born saint to be canonized by the Catholic Church. The property had been serving as a museum. Finding a place with such rich history and character felt like fate, and it wasn’t long before we knew it was meant to be our next adventure.”

What inspired you to turn it into an Airbnb? 

“There’s a kind of poetry in converting a house once home to nuns back into a house for people. In many ways, the core function hasn’t changed all that much; it’s still a place where people can gather and find comfort.”

What challenges did you face with the renovation? 

“The biggest challenge was Bar Harbor’s location. It’s an island, which complicates a lot, especially when trying to manage a construction project from several states away. The nearest hardware store is more than an hour and a half drive, so forgetting even a single nail could set us back by hours. On top of that, skilled tradespeople are in short supply, with wait times for work sometimes stretching over two years. To give you an idea of what we faced, one time, we had contractors show up to tile the kitchen at midnight while we were sleeping in the house. For the brickwork, we had to fly in masons all the way from Virginia to keep the renovation on track. My husband, David, once had to fly back to the property for 12 hours to finish the back porch before our first official rental. Despite these hurdles, the project was absolutely worth every challenge.”

What did you make sure to preserve at the property?

 “We did not have historical restrictions because the majority of the renovation was interior. But we really tried to preserve as much as possible. There is a secret confessional panel that slides down in the chapel. The stained glass windows are original, and the bell system for each of the rooms. One of our favorite transformations was turning the old chapel into a stunning living room. The space is still deeply spiritual; when walking into it, you can feel a sense of peace. The windows are an experience all their own: clear and bright by day, shimmering emerald green at night. It’s truly the coolest room I’ve ever seen, and it sets the tone for the entire house.”

How much did this convent cost to renovate, and how does it perform as a rental? 

“Our renovation costs almost equaled the amount that we paid for the house. Since then, the recent appraisal for the house has increased 400% from the original purchase price. [As a short-term rental] I can say that it performs really well, and the ROI has been absolutely worth it.”

What type of guests does your convent attract? 

“We welcome many visitors seeking religious and spiritual experiences. Many Catholics come specifically to see the former home of St. Katharine Drexel, as it’s a deeply meaningful and holy place for them. We’ve also hosted nuns, young women on yoga retreats, and others drawn to the spiritual atmosphere. With such a serene environment, we truly believe this is an ideal place for anyone seeking peace and reflection.”

Was this your first real estate investment property, and what have you learned from the experience?

 “Yes, this is my first real estate investment. I definitely didn’t start small! I’ve learned that a unique property stands out from the competition. Since then, I have invested in multiple other properties. We want to look internationally next, and we were in Greece looking last week.”

Have you—or any of your guests—taken a “vow of silence” at your convent? 

“I certainly haven’t taken a vow of silence myself—I’m a lawyer and a parent to eight kids, so quiet moments are few and far between. That said, my Gen Z daughter often mentions how much she values sanity and peace, which seems to be a growing trend among her generation. I wouldn’t be surprised if we start seeing more Gen Z guests seeking out the serenity this space offers in the future.”

Check out the full story and photos of Crawley’s awe-inspiring renovation below.

How to convert a convent into an Airbnb

Investors are renovating convents and monasteries into TikTok-worthy vacation rentals. 

No nuns? No problem. Turn convents into Airbnbs

Michael Jordan fans can now be like Mike by renting the house where he used to live: The Chicago-area mansion, 

, runs just over $100,000 for a weeklong stay.

, boasts nine bedrooms (seven currently with beds), 15 full bathrooms, five half baths, and can accommodate up to 12. Guests can kick back like His Airness and sink three-pointers on the regulation-size basketball court, play golf on a putting green, fish in a private pond, swim in the infinity pool, or head indoors for the movie theater, pool tables, cigar lounge, and more amenities worthy of an NBA All-Star.

Jordan built the house over several years and completed it in 1994 while he was playing for the Chicago Bulls. He listed it in 2012 for $29 million. It then sat, infamously, on the market for 12 years until it was purchased in December for $9.5 million by John Cooper, a real estate investor at Han Capital in Illinois.

So what inspired Cooper to purchase this iconic property? “I have larger plans than having this be a short-term rental; however, they require zoning relief, which could take months or even years, if ever,” he told 

. “So in the meantime, I’m considering various options that are allowed within the current zoning district to produce revenue.”

Highland Park, where Champions Point is located, permits only 45 days of short-term rentals annually, which amounts to six weeklong stays per year. Cooper, who listed the property in late June, says he’s already received several booking requests. Does that make this a winning investment, or is it too early in the game to make the call?

Michael Jordan’s former home is hardly the only short-term rental with celebrity ties. Currently, you can book stays at properties formerly owned by 

. Some stars even rent out homes they currently own, such as 

 have rented out their guesthouses for limited periods.

But do these rentals rake in profits? It can go either way.

“The ‘fame premium’ is a marketing tool, not a sound basis for an investment, because the novelty fades but the carrying costs don’t,” says Sabine Ghali, managing director at 

 in California. What really matters are the fundamentals of the property itself, such as its location, rates on comparable rentals, and broad appeal beyond just a niche group of fans.

Sometimes, a celebrity’s customizations, from recording studios to basketball courts, can be a liability. “These features can shrink the pool of interested tenants for a short-term rental, making the property harder, not easier, to monetize consistently,” Ghali adds. These signature features can also make a house harder to sell, which explains why Jordan’s home lingered on the market for over a decade.

Furthermore, “The fame of the previous owner can bring higher security concerns and inflated guest expectations, which can lead to issues with upkeep and guest satisfaction,” points out real estate broker 

 of Paramus, NJ. “As an investment, these properties require careful management. The hype surrounding a celebrity’s name can generate buzz, but it’s crucial to ensure the home itself offers real value beyond the name.”

So, time will tell whether enough fans will fork over $100,000+ to walk in Jordan’s hallowed halls. The rest of us will have to make do with a virtual tour by viewing a few pics below.

Do celeb homes make profitable Airbnbs? 

Michael Jordan’s former home is now a short-term rental. Is it a slam-dunk investment? 

Do celeb homes make profitable Airbnbs?

What does it take to make untamed land not only livable, but luxurious? Janice Wilson found out in 2021 when she and her husband purchased 10 acres of coastal forest in Joyce, WA, for $375k. On it, they built 

, a retreat that celebrates a trend called “forest cocooning,” where couples can unplug from the stress of modern life and reconnect with each other. Here’s how Janice carved out her own version of paradise in the woods.

What inspired you to build this glampground?

 “This is my dream campground. My husband and I love dispersed camping [camping outside of designated campgrounds]. But as a chick, I’m not a fan of the squat. Park reservations rarely provide a true immersion in nature, as the campsites are typically within line of sight. And typical glamping outfits feel more like a Civil War reenactment than a nature retreat. Instead of being ensconced in nature, I felt claustrophobic in a sea of white canvas. I’m also not a fan of communal bathrooms—at all. So Menizei is my sweet spot.”

What was the land like when you bought it, and how long did it take to build up?

 “The land was untouched: no power, no septic, no water. Just towering conifers and a humbling view of the Salish Sea. For site infrastructure, we put in water, electric, and septic. All in, that effort spanned three calendar years, although actual time was closer to two years, and cost about $125k, the most expensive component being the septic system.”

 “The biggest challenge was the permitting process. Clallam County, where we’re based, was lovely. We experienced none of the bureaucratic horror stories that developers in other parts of the country share. We considered the county to be a true partner in favor of stewardship tourism. I was proactive and sought to be above board from day one. I think that helps the county help you. The only issue has been with our neighbors about classic easement issues involving the scope of the access rights to our property. Although our easement is broad and expansive, a determined neighbor can always find something to argue about. If we had lawyered up earlier in the venture, we might have circumvented the legal challenges thrown our way, now four years in the making. My only regret is not hiring a land use attorney for our Conditional Use Permit hearing. We’d likely have saved north of $100k.”

 “Today, Menizei is a profitable, design-forward glamping destination offering biophilic basecamps with our signature blackout tents, floating bathhouses designed by the award-winning architectural firm GO’C, private saunas; each is completely private, tucked in a coastal forest—all tailored for couples seeking to disconnect from the urban grind and reconnect to nature. And each other. And no squatting. Our guests [rave] about the bidet.”

 “Leveraging crowdfunding, we launched in 2024 and sold out our first season. Despite operating for fewer than 100 days per year, annual revenue in 2024 was $239k. This year we’re averaging a higher average daily rate around $568, although booking windows are considerably shorter, and we’re on track to exceed $300k this year with a gross margin of 68%. We were recently featured in 

What have you learned through this process?

 “Raw land often comes with murky easements, unclear access rights, or legacy disputes with neighbors. We learned this the hard way. Don’t assume 

 means building whatever the hell you want without interference. Engage legal counsel early, especially if buying rural land. What you spend up front on a land use attorney can save tens (or even hundreds) of thousands in future legal headaches.”

Got any advice for others who dream of developing a glampground?

 “Design for your category, not for volume. The foundation of quiet luxury is seclusion. We invested in the experience rather than the number of units. With only three sites, we created space for guests to fully immerse themselves in nature. Our average daily rate makes up for quantity. And treat your parcel like a canvas, not a product. We didn’t bulldoze or ‘develop.’ Every path, light, and basecamp was placed in deference to what was already there. Guests appreciate when the architecture conforms to nature and not the other way around.”

How to build a glampground

Floating bathhouses with bidets in the woods? Welcome to the trend of “forest cocooning.”

“I turned raw land into a luxury glampground”

Right when most Americans are kicking back, Airbnb hosts are kicking into high gear: July Fourth marks the peak of summer rental season, and the top markets aren’t where you might think.

 found that the most packed area for bookings during the July Fourth week is a tie between the Florida Panhandle and the Alabama Gulf Coast, with an occupancy rate of 67%. Who would have guessed?

The popularity of these two destinations may, in part, boil down to budget constraints. Although short-term rental rates in upscale beach destinations like the Hamptons on New York’s Long Island can cost several thousands of dollars a day, fees in the Florida Panhandle and Alabama Gulf Coast average just over $600 per day over the July Fourth weekend.

Beyond also found that this summer’s vacationers are suffering from the strains of an uncertain economy—showing greater price sensitivity, booking shorter stays, and waiting longer to lock in their plans. Summer 2025 travelers booked just 

, an 11% decrease from last year. Some guests may be holding out in the hopes of landing a last-minute deal.

Travelers also gravitated to rentals within driving distance rather than flying further afield. “People still want to take trips, but those trips might be closer to home,” said Julie Brinkman, CEO of Beyond. “They need to know that they have job security, that they’re able to fund their trip.”

Even though summer travelers are leery of overspending, STR hosts in the top markets are still raking in decent profits and stand to make $1,200 this holiday weekend (July 4–6) and over $64,000 by the end of the year.

July marks the height of the short-term rental season—and the most profitable month for hosts nationwide. During this peak, nightly rates for guests average $474, while hosts earn an average of $381 per available night. After that, day rates (and profits) slide downward as the temperature cools, bottoming out in January at $67 per night. Which, come to think of it, makes that a great time to book your next bargain vacation.

Where people book Airbnbs for July 4th

America’s on vacation right now—and the busiest short-term rental markets might surprise you.

Guess where everyone’s celebrating July 4th? 

Curious what it takes to turn a dilapidated old house into a popular party venue? Andy Saintilus learned the ropes after purchasing a three-bedroom, two-bath fixer-upper in Miami for $202,500. He then spent $150,000 over 10 months renovating it into an 

, which now earns $423 per night and has raked in a total of $400,000 over the past four years. Here’s his story, plus before-and-after pics that prove just how far a fixer-upper can go with a little elbow grease and creativity.

 “I spent 16 years in sales, but once I saw colleagues getting laid off, this made me realize how dependent I was on a traditional nine-to-five job. Motivated by the need for financial security and independence, I pivoted into real estate investing. I started by acquiring rental properties, then expanded to short-term rentals.”

What were some of the biggest challenges?

 “There were many moments in my journey when quitting would have been easy. For example, tenants damaged my properties after I had invested a lot of money in them. I also bought my first short-term rental just before the pandemic hit.”

 “I didn’t have much experience, but I did know how to create a fun and unique experience. So, I designed the property to reflect my idea of a great time. I finished renovations in 2021, right around the time travel restrictions were lifted. That timing worked in my favor, and the property ended up being one of my most profitable investments.”

Any advice for others who want to become an Airbnb host?

 “I recommend working with a mentor. That’s how I got my start, and it’s why 

 who have successfully launched their first Airbnbs. There are multiple ways to fund your first property—some investors use their 401(k), others rely on personal savings. You can also partner with a co-host, but it’s important to understand the difference: A mentor guides you through selecting a property, renovations, and creating an experience, while a co-host primarily helps manage the listing once it’s live.”

What tips do you have for picking a property with potential?

 “Location matters, but the guest experience is what truly sets you apart. In Florida, for example, a pool is a major advantage since the weather is warm year-round. Beyond that, it’s all about designing a space where people can relax and enjoy themselves. The great thing is that we all have different definitions of fun, and setting up your Airbnb allows you to bring your vision to life while attracting like-minded guests.”

Check out more before-and-after photos of Andy’s investment below.

How to open an Airbnb

Here’s proof that even the most run-down wreck of a property can be transformed into a profitable short-term rental.

“I turned a $200k fixer-upper into a $400k Airbnb”

Once upon a time, Airbnb hosts could pop a few colorful throw pillows on their foldout couch and make a killing. But no more.

“The STR game has changed drastically,” says Andy Saintilus, a short-term rental (STR) host in Florida with six properties. Five years ago, when he started, “You could list a basic home with generic furniture, minimal amenities, and no Wi-Fi, and still get booked. Today? It’ll sit empty [unless] you offer more than just a place to sleep. You have to build an experience.”

Saintilus pulled out all the stops to deliver, adding outdoor kitchens, arcade machines, putting greens, basketball courts, and more. Although these upgrades cost a lot upfront, they paid off. “They’ve nearly doubled my nightly rate,” he says. “But they’ve also come with more responsibility and cost. Turf looks great until trees start dropping fruit and leaves. And no matter how clean the space is, some guests expect it to be flawless 24/7.”

Although his business is profitable, and he 

 on how to follow in his footsteps, Saintilus now warns them: “It’s no longer passive income,” he says. “It’s a full-scale hospitality operation, and if you don’t treat it like one, you’ll fall behind.”

“Running a short-term rental today is nothing like it was even three years ago,” agrees Andrea Clarkson, an Airbnb Ambassador, STR design consultant, and author of 

Stylish Stays: The Complete Guide to Airbnb Design, Setup, and Success

. “You used to be able to stand out with a decent bed and cute throw pillows. Now? Guests are comparing your place to boutique hotels.”

, she invested in design-forward furniture, layered lighting, and “moments” like cozy reading corners and luxe bathroom setups. “I also designed my own welcome guide and a brand identity—name, logo, story to give the place personality,” Clarkson says. “It worked: We’ve seen more bookings, better reviews, and guests sharing the space on social like it’s a lifestyle destination.”

Some hosts have joined forces with outside partners like 

, which has transformed over 150 passive rentals across the country into “wow”-worthy experiences by adding welcome champagne in ice buckets, on-site sommeliers and private chefs, daily housekeeping on demand, 24/7 textable concierges, heated plunge pools, and other amenities. These upgrades don’t come cheap: In one rental in Sag Harbor, NY, a Rove property owner invested $85,000 into overhauling the landscaping and adding a James Turrell–inspired LED light installation. But overall, these improvements boost rental revenue by an average of 40% over what the property was collecting previously.

“The STR arena has become a knife fight,” says Rove CEO Jonah Hanig. “Soaring supply, day-rate compression, and AI-driven pricing tools mean that ‘nice house, good photos’ no longer cuts it.”

“It’s definitely become more competitive to win short-term rental bookings, noticeably so in the past 12 months,” agrees Christina Melander, an STR host and founder of 

. “I think three forces are driving the trend: a huge increase in the number of STRs, economic uncertainty making people less inclined to travel, and boutique hotels raising guest expectations and creating an amenities arms race.”

But Melander has found that she doesn’t need to spend tons to dazzle guests. At her 

, “We always welcome guests with a freshly baked loaf of banana bread made by my sister Heather,” she says. At her 

, “I sourced most of the furnishings from thrift stores to create a one-of-a-kind space that’s the antithesis of generic, off-the-rack styling. Heather painted a mural on the pool gate. These aren’t over-the-top, flashy additions, which I think can feel gimmicky; rather, they’re impactful updates that wear well.”

Whether they spend a little or a lot, Airbnb hosts say they must work harder to keep guests happy.

“We treat it like a business, not a side hustle. This mindset is key to staying competitive in a demanding market,” says 

. “We’ve leaned into higher upfront investment because we know guests will pay for a turnkey, Instagrammable experience.”

“This is a classic early adopter issue: The first wave of Airbnb hosts were riding a blue ocean: No competition, no standards, and plenty of bookings made a lot of people fat and happy. But that’s not where we are now,” says Sarah Thomsen at 

, who opened two STRs in Colorado two years ago, right when the market was heating up. In Dillon, she branded her mountain property, 

, as a high-end alpine escape with a wood-burning fireplace and luxury bedding. In 

, she leaned into remote work setups and lounge vibes. Even though she’s new to hosting, both units outperform comparable properties.

“That’s not a fluke,” Thomsen says. “It’s design, intentionality, and guest experience. Financially, the effort has paid off. But it’s not passive. It’s hospitality.”

The challenges of running an Airbnb

Short-term rentals have gotten so competitive that hosts treat their properties like White Lotus–level hotels. 

Is your Airbnb fancy enough? 

, Portland’s most famous floating home, which is currently for sale for $999,000.

Located on the Columbia River, this 2,737-square-foot home’s space-aged design and curvy aluminum walls have garnered appearances on 

. It’s all but begging to be turned into an Airbnb, and as luck would have it, the Sundance Marina where the Aqua Star is moored allows for short-term rentals.

But what’s it like to actually own a floating home? To find out, I chatted with the listing broker 

, who’s also a contractor for floating homes and has lived in them for 24 years. Here’s what he had to say about these unique living quarters and his hopes for the Aqua Star.

How were you first introduced to the idea of floating homes?

 “I was always a water person, a jet-skier going up and down the channel thinking, ‘Man, look at all these floating houses. If I just lived here, I wouldn’t have to deal with the boat ramp and I’d be here all the time.’ So I put up flyers around marinas: ‘Contractor wants to trade work for discounted rent’ kinda thing. Then I landed my first rental, then I bought one, then I bought another one. So it was kind of a destiny.”

How many floating homes are there in your area, and what’s the best part of living in one?

 “Around 2,400. A lot of residents say, ‘When I get home, I feel like I’m on vacation.’ People are smiling, and they say hello. You could be in a subdivision somewhere and never know your neighbors, but here it’s a different mindset.”

What are the biggest challenges of owning a floating home? For starters, how are they built?

 “The construction is done on the water, with cranes and barges. The foundation is typically logs, but the logs aren’t what floats the house. It’s big Styrofoam blocks wrapped in plastic that they drop in the water with weights, then swim into place. Each brick offsets 800 pounds of buoyancy. When people move in or out with a lot of furnishings like a piano or hot tub, then you may have to add or remove some.”

 “Above water, it’s the same. Below, the float degrades over time. You have to inspect them and add shims or make repairs. Labor costs are also higher because everything has to be carried down ramps and docks. And if a contractor shows up with a level, they don’t know what they’re doing—floating homes shift slightly, so you have to use your eyes.”

Are floating homes impacted by bad weather or floods?

 “Most floating homes are in flood zones but aren’t required to carry flood insurance because the homes and the docks are designed to rise and fall with the water. The 100-year flood of 1996 is a prime example. The parking lots were flooded, but all the floating homes were just sitting there just fine.”

How does financing work for floating homes?

 “They are considered personal property, not real estate. We have three or four floating home–specific lenders that offer 20- to 30-year loans based on the float’s condition. And 20% down is required.”

Are floating homes more or less expensive than land homes?

 “Per square foot, they’re usually similar, but resale depends heavily on location, the condition of the float, and whether the slip is owned or rented. For the Aqua Star, there is a separate $2,060-per-month fee to rent the slip.”

What do you think of the Aqua Star’s potential as a real estate investment?

 “It’s rare to find a floating home in a place that allows short-term rentals. There’s even room around the Aqua Star to add seven or eight more floating homes. It’s a mini-development opportunity.”

If these homes float your boat, scroll down to see more pics of the Aqua Star and Dan’s own water-worthy residence.

Short-Term Rentals

No nuns? No problem. Turn convents into Airbnbs

Do celeb homes make profitable Airbnbs?

“I turned raw land into a luxury glampground”

Guess where everyone’s celebrating July 4th?

“I turned a $200k fixer-upper into a $400k Airbnb”

Is your Airbnb fancy enough?

Inside the world’s most famous floating home

Let’s Make a Game Plan