Leonardo DiCaprio pays property taxes on a 104-acre island off the coast of Belize. Johnny Depp’s real estate portfolio includes a 45-acre island in the Bahamas. And not to be outdone, illusionist David Copperfield has his own archipelago called Copperfield Bay. Rihanna has a palatial pad in her native Barbados. Mick Jagger’s Mustique retreat has hosted rock royalty for decades, and Oprah Winfrey escapes to her estate in Antigua when she needs a break from Montecito.
And those are just a few of the VIPs who own a slice of the Caribbean. Best of all, some of them are up for rent for your next vacation.
From a jungle retreat in Jamaica to a supermodel-friendly sanctuary in Turks & Caicos, here are the three coolest celeb-owned vacation homes you can book right now.
Diplo’s jungle retreat
Grammy-winning DJ and producer Diplo spent seven years building his private paradise, Pompey, in Port Antonio, Jamaica. The result is a jungle hideaway that blends natural elements with high-design aesthetics — plus a professional recording studio that has already birthed over 100 songs.
“Half of your studio time should be taking a break anyway,” Diplo tells the Post, explaining why the space includes a polycade and ping pong table made of reclaimed wood from Mexico. So far, the studio has drawn an eclectic mix of artists — both paying guests and friends of Diplo. His neighbor Grace Jones recently stopped by at 3 a.m. to record what he describes as a “wild song that will never be heard.”
As much as he loves his studio, Diplo’s favorite room is the library where he likes to watch old movies with his son. It features a full glass wall overlooking the jungle, a massive analog music collection featuring 3,000 records, and several rare art pieces.
Pompey opened to the public last year — starting at $100,000 per week — with a perk unlike any other rental in the world: it keeps guests happy with some of the island’s finest organically grown ganja, sourced from farmers in Port Antonio.
But the focal point of the property is the outdoor dining area. It’s the best place to take in the estate’s surroundings — including a British cannon sourced from an antique shop in Kingston.
The only downside of Pompey is it’s not entirely private. You’ll have to share the property with Diplo’s four horses, a donkey, a milking cow, and goats. He says sheep and chickens will be arriving soon.
As for Pompey’s availability, Diplo says he usually is only there in the fall. That said,
February is his favorite time to visit: “It’s not too warm or rainy and the days are still long enough to get everything done.”
Branson’s eco-escape
Sir Richard Branson may call Necker Island his primary home in the British Virgin Islands. But when the billionaire business magnate wants something even more exclusive, he retreats to the Branson Beach Estate on neighboring Moskito Island. The estate, which accommodates up to 22 guests across three villas, is perched on a dramatic outcrop with sweeping sea views. Each of the villas, connected by treetop walkways, have their own personality.
“It’s extremely hard to pick a favorite,” Branson said. “All three are unique, from the interiors to the views.”
But Headland House is where he and his wife Joan usually stay when they visit two to three times per year. “My kids Holly and Sam prefer the other two villas, which are nearer to the beach,” he adds.
New in 2025, guests can book individual villas (from $20,000 per night) instead of renting the entire estate (from $51,000 per night), making it more accessible for smaller groups.
Branson is also ramping up his efforts to be more eco-conscious. For example, the estate employs a high-efficiency glass recycling machine to turn glass bottles into sand for the island’s beaches.
The estate offers private pickleball courts, direct ocean access (unlike the other properties on Moskito Island), and personal water sports instructors.
Who does Branson hope to share his home with? “Anyone who loves having fun, doing activities like tennis, kite-surfing, hiking, pickleball, a bit of partying and relaxing too.”
Brinkley’s sanctuary
For nearly two decades, Christie Brinkley has owned Lucky House, a three-bedroom beachfront estate at COMO Parrot Cay, the ultra-exclusive private island resort in Turks and Caicos.
The supermodel even celebrated her 70th birthday here last year. Built in 2003 and available to rent since 2004, Lucky House offers a newly upgraded outdoor deck and pool area, blending seamlessly into the surrounding pristine sands.
The home is available year-round for $12,000 to $18,000 per night, pending Brinkley’s approval.
But Brinkley isn’t the only A-lister with a rentable retreat at COMO Parrot Cay. Rolling Stones guitarist Keith Richards is happy to share his three-bedroom Rocky Point Villa, which comes with a private infinity pool and an outdoor gazebo.
Fashion mogul Donna Karan’s two-story residence, The Sanctuary, rents for $18,000 to $25,000 per night.
All rentals at COMO Parrot Cay come with a private butler and access to the resort’s world-class spa and private beaches.