Five Ultra-Expensive Private Islands That Reshaped Global Luxury Real Estate Over the Past Decade

For those dreaming of escape from dreary winters, few fantasies rival owning a private island paradise. The world’s wealthiest individuals have turned this fantasy into reality, acquiring some of the planet’s most expensive island properties. These acquisitions represent not just personal playgrounds, but significant investments in global real estate. Here’s a look at five of the most notable expensive island purchases by billionaires and celebrities over the last decade — and what makes each one special.

Oracle Co-Founder’s $500 Million Makeover in Hawaii: The Lanai Story

When Larry Ellison acquired 98% of Lanai, a 141-square-mile Hawaiian island, he wasn’t simply buying a tropical getaway. The Oracle founder’s $500 million island investment aimed at transforming the entire community. With more than 3,000 residents calling Lanai home, Ellison focused on infrastructure development and economic growth rather than personal indulgence. According to Pacific Business News, Lanai ranks as the largest privately held island in the United States, boasting nearly 50 miles of pristine coastline. The island now hosts several luxurious Four Seasons resorts, making this expensive tropical destination accessible to wealthy travelers seeking world-class amenities and stunning landscapes.

Shakira’s Bohemian Paradise: The $16 Million Bonds Cay Venture

The pop star’s musical collaborators — including Pink Floyd’s Roger Waters and Spanish singer Alejandro Sanz — joined forces with Shakira to purchase Bonds Cay in the Bahamas for approximately $16 million. Located 120 miles off Florida’s coast, this 700-acre expensive island features five pristine beaches, immaculate white sands, and three scenic salt pond lakes. The trio’s vision transforms this tropical expanse into an eco-friendly luxury retreat and artists’ haven, positioning the island as a destination where creativity meets sustainability.

Québec’s Fairytale Island: Celine Dion’s $25.5 Million French Manor

Not every expensive island destination offers warm tropical breezes. Celine Dion proved this with her private island retreat on the Rivière des Mille Îles in Quebec. She constructed a magnificent mansion styled after a French Norman chateau, accessible only via a private gated bridge — a detail that elevated the property’s fairy-tale allure. However, Dion’s tenure on the island proved temporary. She sold the property in 2016 for $25.5 million, moving on from what was once her exclusive North American sanctuary.

Skorpios Island’s Greek Crown: The $150 Million Record-Breaking Purchase

When Bill Gates, Giorgio Armani, and Madonna set their sights on Skorpios Island, they expected to claim this 74-acre Greek paradise. Famous for its stunning natural beauty and historical significance — it’s where shipping magnate Aristotle Onassis married Jackie Kennedy — this expensive island attracted global attention. Yet the trio’s ambitions were thwarted. Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, ultimately secured the prize, purchasing Skorpios and its neighboring islet Sparti for an astounding $150 million, making it one of the priciest island transactions on record.

Larry Page’s Tropical Investment: The $32 Million Puerto Rico Acquisition

Google co-founder Larry Page entered the expensive island market in 2018, demonstrating that tech billionaires have a particular appetite for private paradise. Through an LLC called U.S. Virgin Island Properties, Page acquired Cayo Norte — Puerto Rico’s largest privately owned island — for $32 million. This tropical gem captivates with its glittering white-sand beaches, vibrant coral reefs, and diverse wildlife, including endangered sea turtles. The acquisition underscores how ultra-wealthy investors view expensive island properties as both lifestyle statements and potential long-term assets.

The trend is clear: for the world’s elite, owning an expensive island represents the ultimate status symbol and investment opportunity. Whether serving as personal retreats, development projects, or artistic sanctuaries, these acquisitions demonstrate how billionaires and celebrities continue reshaping the global luxury real estate landscape, one expensive tropical destination at a time.