Why Billionaires Are Betting Big on Private Islands: The Mega-Deals Behind the World's Most Exclusive Real Estate

Private islands have become the ultimate status symbol for the world’s ultra-wealthy. Beyond the allure of pristine beaches and luxury resorts, these properties represent serious real estate investments and personal sanctuaries away from public scrutiny. Here’s a breakdown of the most expensive private island acquisitions in recent years—and what they reveal about how billionaires spend their fortunes.

The Tech Titan’s Tropical Expansion: Larry Ellison’s Lanai

When Oracle co-founder Larry Ellison acquired 98% of Hawaii’s Lanai island, he wasn’t simply purchasing a vacation home. The estimated $500 million transaction reflected a broader vision: transforming the 141-square-mile island into a thriving community while upgrading infrastructure for its 3,000+ residents.

Lanai now stands as the largest privately-held island in the United States, stretching nearly 50 miles of coastline. Rather than gatekeeping the paradise, Ellison developed multiple Four Seasons luxury resorts, making the island accessible to affluent travelers. This approach blurs the line between personal ownership and strategic real estate development—a pattern increasingly common among billionaire island purchases.

A Greek Jewel Changes Hands: The Skorpios Story

Skorpios Island, the legendary 74-acre Greek property where shipping magnate Aristotle Onassis once married Jackie Kennedy, attracted some of the world’s most discerning collectors: Bill Gates, Giorgio Armani, and Madonna all reportedly set their sights on it.

Yet none of them secured it. Russian billionaire Dmitry Rybolovlev’s daughter, Ekaterina Rybolovlev, outbid them all, purchasing Skorpios and its neighboring islet Sparti for a staggering $150 million in 2017. The acquisition underscores how intensely the ultra-wealthy compete for historically significant properties—where the price tag reflects cultural prestige as much as physical assets.

The Musician’s Eco-Retreat: Bonds Cay Reimagined

In a rare collaborative venture, Shakira teamed with Pink Floyd’s Roger Waters and Spanish singer Alejandro Sanz to acquire Bonds Cay in the Bahamas for approximately $16 million. The 700-acre island, featuring five pristine beaches and three salt ponds, became the foundation for an ambitious eco-luxury resort and artists’ retreat.

Located 120 miles off Florida’s coast, this project demonstrates how celebrity wealth increasingly flows into sustainable tourism ventures rather than purely personal consumption.

Quebec’s Fairytale Property: Celine Dion’s French Norman Dream

Celine Dion’s private island on the Rivière des Mille Îles in Québec took a different approach to island luxury. Instead of a beach paradise, she constructed a French Norman chateau-style mansion on the property, accessible only via a private gated bridge.

The arrangement proved temporary. In 2016, Dion sold the island property for $25.5 million, suggesting that even for mega-stars, the remote island lifestyle isn’t always permanent—a reminder that ultra-luxury assets can shift hands relatively quickly within wealthy circles.

The Google Founder’s Puerto Rican Acquisition

Google co-founder Larry Page added to his portfolio with the 2018 purchase of Cayo Norte, Puerto Rico’s largest privately-owned island, for $32 million. The acquisition, executed through the LLC “U.S. Virgin Island Properties,” positioned Page alongside Ellison as a tech billionaire with serious island real estate holdings.

Cayo Norte boasts pristine white-sand beaches, coral reefs, and wildlife refuges for endangered sea turtles—natural assets that increasingly appeal to environmentally-conscious ultra-wealthy investors who own the biggest private islands globally.

The Pattern Behind the Purchases

What ties these transactions together? They reveal that private island ownership among billionaires extends far beyond vacation homes. Whether it’s Larry Ellison’s community-focused development model, Ekaterina Rybolovlev’s trophy acquisition strategy, or Larry Page’s portfolio diversification, island purchases reflect how the ultra-wealthy deploy capital across multiple asset classes and geographies. Each transaction tells a story about power, vision, and the lengths to which billionaires will go to secure Earth’s rarest real estate.