Fantasy island? What it’s really like to own a private paradise

The answer, like the island itself, is anything but simple
East Sister Rock island

Photo by Wesley Williford

There are dozens of private islands scattered off the coast of Florida. The Willifords own one of them. For almost 30 years, it has been a sanctuary for their family—and also a source of strain. Now they must decide whether to keep it or let it go. The answer, like the island itself, is anything but simple.


From a bird’s eye view, it is exactly how you picture a private island. A circle of white beach surrounded by vast Atlantic waters, a simple tin-roof house in the middle. There is a pool, a sundeck, and a small helicopter landing pad. A one-room guest cottage overlooks a 100-foot dock. Palm trees drop the occasional coconut. A rocky barrier encircles the island, trapping a shallow moat of water that glows emerald beneath the sun.

Lush vegetation flanks a pathway to the dock

Photo by Harold Daniels

The island, called East Sister Rock, is a quarter mile off the shores of Marathon, Florida, in the middle of the Florida Keys. Visible from the mainland, its 1.4 acres have fascinated many a binocular-wearing traveler and become a favorite flyover spot for helicopter tours. For $11,000, groups of six can spend a week on the island, snorkeling with rays, kite surfing right off the dock, and fishing for snook. They can wave at the pleasure boats that slow to check the place out. They can pretend East Sister Rock is theirs.

But the real owners of this island are not what you might picture. They are not celebrities nor Silicon Valley expats, but a hardworking family of six. The Willifords do not live on East Sister Rock; their home is the Miami suburb of Coral Gables. They bought the island in 1995, when it was a house and little else, and built its complex, off-grid electrical and water system on their own. When Hurricane Irma destroyed all but the home’s cement walls in 2017, they had no insurance, and they spent a year rebuilding everything themselves. Each Saturday, they commute two-and-a-half hours to the island to launder and scrub it before new renters arrive. They patch its holes, mend its hammocks, sand and paint its dock. The Willifords outsource nothing.

The Williford family—Elena, Marissa, Bob, and Wesley—on East Sister Rock island

Photo by Harold Daniels

Their plan has always been to keep the house in the family, a gift for future generations. But they also have it on the market. They are conflicted about the island—within the family, within themselves. “It is paradise,” says Bob Williford, the family patriarch. “But nothing about it is easy.”


In 1995, a doctor from New York put East Sister Rock up for sale. He had built a simple house on it some 15 years prior, when private islands weren’t yet a real-estate sector and environmental regulations were lax. The house had no electricity and a small cistern to hold rainwater. Sale price: $750,000.

The Willifords’ Carolina skiff shuttles them between the island and Marathon, Florida

Photo by Harold Daniels

Bob’s wife, Elena, was pregnant with their third son. She and Bob, a contractor, owned a vacation condo in Marathon, but once the baby arrived, the space would be too small. As they paged through real-estate listings, Bob spotted the island’s pre-auction advertisement. “He had always dreamed of owning a place he could make completely solar- and wind-powered and live off the grid,” Elena recalls. “He wanted to see it.”

“Why wouldn’t I?” Bob says. “No electric bill, no water bill. And it looked like a decent place.” Born and raised in South Florida, Bob is as unfiltered as a cup of Everglades water. He delivers both facts and jokes with nonchalant bluntness; he drapes his arms around his adult kids as if they’re still small. He met his wife in Miami in 1983, when he was an up-and-coming builder in need of a permit and she the government clerk handling his request. “I liked the way she talked,” he says of the accent Elena developed as a child in Cuba. “And I liked the way she licked envelopes.”

The Williford boys on their island home’s wraparound porch in the nineties

Photo by Harold Daniels

Cringeworthy comments aside, the story has a feel-good ending: He asked Elena on a date, she agreed, he had a motorcycle, they went riding off into the sunset. “She chased all my other girlfriends away,” he says, smiling broadly as Elena rolls her eyes. “But now, I don’t want to be anywhere without Mami.”

Elena—Mami to everyone in her family—is wary of too many questions and protective of the details of her life. “I’m much more private than Bob,” she says. It’s part of what makes her the family backbone, the person who quietly keeps things running behind the scenes while also keeping an eye on her children. There are four Williford kids now, all of them grown and living in South Florida. Two of them still reside under Bob and Elena’s roof. “To some people, that might seem strange, but I’m Cuban,” she says. “We like to have our families together.”

Bob and Elena Williford

Photo by Harold Daniels

It was this idea of togetherness that compelled Elena to take a boat to the island with Bob and her young sons and see it for herself. The three-bedroom, two-bathroom house was made of solid concrete poured atop 80 pilings that lifted it 15 feet above sea level. A near-constant breeze made the hammocks on the wraparound porch sway. Baby nurse sharks wriggled within the safety of the moat. As Elena held her boys’ hands and walked them through the house, she spotted Bob outside the window speaking to the real estate agent. “As soon as we left, Bob announced, ‘I just bought the island,’” Elena says.

She wasn’t surprised, nor was she daunted. She had fled Cuba with her family in 1968, when she was eight years old. She’d built a life and a family in America. “This,” she says, “was just a new adventure.”

For Bob and Elena, memories of the next few years are bathed in a golden light. The Willifords spent nearly every weekend on the island, often bringing Elena’s parents—los abuelos—with them. Bob slowly created the off-grid system of his dreams (complete with state-of-the-art solar panels and a 15,000-gallon rainwater tank) while Elena cooked arroz con pollo and shrimp paella over a fire. The Willifords had a fourth child, a girl, and didn’t bother keeping clothes on any of the kids while they were away from the mainland.

It was more Gilligan’s Island than Lifestyles of the Rich and Famous, but that didn’t bother them. “It was like camping,” Elena says. “We traveled to the island with bags of ice to keep us cool. We had to turn on the generator to heat baby formula.”

Wesley Williford and his girlfriend, Mary Jane Perun, on one of the island’s many hammocks

Photo by Harold Daniels

On Sundays, when it was time to return home, the Williford children would hide in crevices beneath the porch. Once found, they’d sneak crabs home and bring their stowaway pets to school to show their friends. Teachers called Elena; Elena lectured her children. “I would tell them, ‘Don’t let anyone know we have an island,’” she says. “I imagined what people might think.”

But their friends eventually found out. Wesley, the 29-year-old second-born, recalls learning as a teenager that all his buddies were speculating about his parents’ jobs. “People thought we had to be drug dealers,” he says with a smile.

“As a symbol of great possession, the privately owned island may yet supplant even the steamship.”
Fortune, 1930

Farhad Vladi owns private-island consulting firm Vladi Private Islands. According to him, there are roughly 1,000 inhabitable private islands in the United States. Off the coast of Florida, there are approximately 50. Most do not belong to people with recognizable names. “Rich-rich people, they prefer to rent an island versus own one the paparazzi can find out about,” Vladi says. “That’s why I always say the majority of island owners are poor-rich people.”

The sundeck faces a helicopter landing pad

Photo by Harold Daniels

These poor-rich people grapple with a question to which there is no easy answer: Should they pay to insure their island? Chris Krolow, owner of Private Islands Inc., says annual premiums for very small islands usually begin at $25,000 and can skyrocket from there, quickly reaching six figures. And every year, those numbers go up. “Some owners look at how expensive insurance is and don’t opt for it,” Krolow says. “Then they keep their fingers crossed.”

The Willifords have experienced both sides of the insurance coin. In 2005, Hurricane Wilma tore their island apart. They had insurance, but it would not pay what was needed (citing “acts of God” and all that). The Willifords gave up and eventually dropped their coverage. In came Irma in 2017, and in that particular case, being totally uninsured proved more disastrous than being disappointingly insured. They had to borrow half a million dollars to repair the island all by themselves. (They also took advantage of the months of construction and added a few upgrades, including an in-ground pool.) Today, they pay $28,000 a year for what Elena calls “the ability to relax—a little bit.”

The island’s pool, built after Hurricane Irma

Photo by Harold Daniels

After Hurricane Irma, the Willifords needed to focus on monetizing East Sister Rock. Though they had casually made it available to renters beginning in the early aughts, charging $5,500 a week, they capitalized on its new amenities and “jacked up the price,” as Wesley puts it. Wesley became the island’s chief marketer, touting its 360-degree views and easy accessibility (including a rare perk: unlimited use of the family’s skiff). Like his father, Wesley is unreserved, especially when it comes to talking about the island. He sees himself as the corrector of false assumptions; for example, he wants people to know that East Sister Rock has satellite TV and high-speed internet. “People say to me, ‘I don’t think I could stay on your island. I have to be connected,’” Wesley says. “I’m like: ‘We have everything! We even have Netflix!’”

Interest in East Sister Rock has grown over the years—especially during the pandemic, when rental inquiries jumped tenfold and “the place paid for itself,” Wesley says. The Willifords have earned the right to be picky about who stays there. They used to accept bachelor parties from Miami, until one particularly rowdy group left a toilet sitting outside by the pool. Today, they book repeat families who save up all year to spend a week in a private paradise. When Justin Bieber’s team offered Elena $100,000 to rent East Sister Rock for a week, she flatly refused. “It was already booked,” she says simply.

The Willifords have learned the hard way that irresponsible renters can quickly cost more than they pay. Some have drained their rainwater tank of 5,000 gallons in a week. Others seem to have forgotten that the island relies upon its own power. “It happens more than you would believe: They’ll turn all the lights in the house on, then go to Key West for the day,” Wesley says. “That burns our system.”

East Sister Rock island

Photo by Wesley Williford

And no one understands that system or how to repair it but the Willifords. Bob can explain it simply enough: Solar panels lining the tin roof generate energy for 1,000 pounds of lithium batteries. These batteries in turn provide electricity to the house. Rainwater is collected in the tank and heated by solar power, with a backup electrical heater. If there’s not enough rain, a 2,000-foot water hose is run from the mainland. It takes the hose two days to fill the tank. Still, peek inside the island’s shed and you’ll discover the twisting labyrinth of wires and cords that keeps everything humming; it looks like something belonging to a cartoon mad scientist. When renters are on the island, either Bob or Wesley must stay nearby to solve any issues that arise.

But most calls that come in have nothing to do with the utilities and everything to do with the island’s ocean-locked location. “Saltwater is our number-one problem,” Wesley says. “It’s a destroyer.” At least once a year, he and his father must buy a new, full-sized refrigerator in Marathon, hoist it onto the skiff, and motor it to the island. Then they shimmy the rusted one out of the kitchen and return it to the mainland. The grill has to be replaced every six months. TVs are rarely good for a year. They can never buy enough touch-up paint. “When you’re out here in the ocean, you’re in a battle,” Wesley says. “You’re fighting against nature itself.”


Marissa Williford remembers when the moat’s water reached her waist. The youngest of the Williford kids, she was fascinated by starfish and spent many childhood mornings inching along the watery pathway in search of them. Occasionally she would startle a stingray from its resting spot on the moat’s floor; she felt no fear as it flapped its wings and glided away. So often was she at play in the Atlantic, she felt she belonged there. She was as comfortable with its familiar, if shy, residents as she was with her own family.

Mary Jane Perun and Marissa Williford kayak around the island

Photo by Harold Daniels

Like her mother, Marissa is not one to overshare. The 24-year-old won’t mention that she just finished business school at the University of Miami and is applying to medical school. Her father is the one to proclaim it. She doesn’t talk about the many, many Saturdays she skipped hanging out with friends because she and her family had to clean the island for renters. But after taking a deep breath, she will speak about the prospect of selling it to someone else. “I would be devastated,” she says. “I don’t even like to think about it. I grew up here—it’s my home. It was always the plan for us to take over.”

But plans, like people, evolve. Bob and Elena are getting older, and they say they feel crushed by South Florida’s ever-expanding sprawl. They want to move farther north, maybe to South Georgia. Buy some land and breathe fresh air. Experience more than one season. Make it enticing enough that their kids will come, too. And if all of them move that far, who would look after the island?

In 2016, they went under contract with a buyer. But Hurricane Irma spooked the would-be Robinson Crusoe. It takes a special kind of person to be willing to live under constant threat of destruction, especially as the waters continue to warm and hurricanes line up each summer like planes jammed nose-to-tail at Miami International. No sooner has one taken off than another begins to pick up speed. The only question is where each will land. Any given day, the answer could be the Florida Keys, with East Sister Rock on the front line.

Marissa Williford with some of the family’s dogs

Photo by Harold Daniels

Wesley says he can handle the stress. At this point, he knows the place almost as well as his dad and can fix anything that gets damaged. “Yes, it takes a lot of time and energy to keep this place up, and there’s always the fear of hurricanes,” he says. “But a lot of us want to keep it in the family.”

Says Bob, “Things change. Kids change. As you get older, you have less energy and drive to keep pushing. We’ll keep it for sale and see what happens.”

Bob Williford’s private island is exactly what most people picture. And yet it is not what he himself envisioned, not anymore. It is a place he knows might belong to someone else soon, someone who did not raise their children on it and did not rebuild it, and rebuild it again, with their own hands. To many, his island is a symbol of success. To him, it’s a lot more complicated. From way up high, all you see is the instant beauty of a circular white beach lapped by turquoise waters. But up close, you notice the slow decay of a concrete home whipped by salt-tinged winds.


Private Islands for Rent

East Sister Rock Island
Marathon, Florida
Located a quarter mile from Marathon in the Florida Keys, the island comes with a three-bedroom, two-bathroom house with a guest cottage, pool, and boat. In the morning, wave hello to schools of dolphin. Come evening, lie in a hammock on the wraparound porch and watch for shooting stars. $11,000/week

East Sister Rock Island

Photo by Wesley Williford

Island Camp
Nags Head, North Carolina
Meet your hosts at the Nags Head Causeway or the Manteo waterfront in the Outer Banks, then take a short boat ride across the Roanoke Sound to your own private retreat. The three-bedroom, one half-bathroom house has an outdoor hot shower and views of the famed Bodie Island Lighthouse. $6,000/week

Island Camp

Photo by James Schuler

Old House Cay
Hilton Head, South Carolina
Set among a cluster of uninhabited private islands 10 minutes from Hilton Head Island, this hideaway features a three-bedroom, two-and-a-half- bathroom cottage. Wander the long wooden dock over grassy marshes to watch the sun set over the Atlantic. $3,500/week

Old House Cay

Photo courtesy of Old House Cay

This article appears in the Spring & Summer 2022 issue of Southbound.