The World's Most Expensive Private Islands: A Decade of Ultra-Luxury Acquisitions

Over the past ten years, the world’s wealthiest individuals and entertainment icons have competed fiercely to acquire some of the most expensive private islands in the world. These acquisitions represent not just personal playgrounds but significant real estate investments, ranging from $16 million to $150 million. Understanding who owns these islands and why they sought them offers fascinating insights into ultra-high-net-worth spending patterns and the appeal of island ownership for billionaires and celebrities alike.

The market for luxury island properties has attracted tech billionaires, entertainment moguls, and international entrepreneurs, each bringing their own vision for development and use. From sustainable tourism initiatives to personal retreats, these purchases reflect diverse investment strategies and lifestyle priorities.

Skorpios Island, Greece — The $150 Million Record

The most expensive private island acquisition in this decade occurred in Greece when Ekaterina Rybolovlev, daughter of Russian billionaire Dmitry Rybolovlev, purchased Skorpios Island and its neighboring islet Sparti for an astounding $150 million. This 74-acre Ionian Sea paradise gained historical prominence as the site where shipping magnate Aristotle Onassis married American icon Jackie Kennedy, adding cultural cachet to its natural beauty.

Despite interest from globally recognized figures including Bill Gates, Giorgio Armani, and Madonna—individuals accustomed to acquiring whatever they desire—it was Rybolovlev’s bid that ultimately secured this coveted property. The island’s combination of pristine natural landscapes and historical significance made it a landmark acquisition in the private island market.

Île Gagnon, Quebec — The French Chateau Island

Canadian songstress Celine Dion once commanded attention with her vocal talents; however, her venture into island ownership proved less permanent. She constructed an elaborate mansion styled after a French Norman chateau on Île Gagnon, situated on the Rivière des Mille Îles in Quebec. The property featured a private gated bridge, creating an enchanting, fortress-like atmosphere befitting fairy-tale aesthetics.

Despite the property’s magnificence, Dion eventually relinquished her island sanctuary, selling the estate in 2016 for $25.5 million. The transaction highlighted how even ultra-luxury real estate properties command significant prices in premium markets, particularly when custom architectural features and island isolation are factored into valuations.

Cayo Norte, Puerto Rico — Larry Page’s Tropical Paradise

Google co-founder Larry Page demonstrated particular interest in acquiring private islands in 2018 when he secured Cayo Norte through an LLC named U.S. Virgin Island Properties, paying $32 million for the purchase. Located in Puerto Rico, Cayo Norte ranks as the largest privately-owned island in that jurisdiction and showcases the characteristics that appeal to tech billionaires: exclusivity, natural resources, and development potential.

The island features pristine white-sand beaches, thriving coral reef ecosystems, and wildlife habitats including endangered sea turtle populations. Its ecological significance, combined with recreational appeal, positioned it as an attractive acquisition for technology sector wealth seeking environmental stewardship alongside luxury amenities.

Lanai, Hawaii — Oracle’s Community-Focused Investment

Oracle co-founder Larry Ellison’s 1990s acquisition of approximately 98% of Lanai—a 141-square-mile Hawaiian island—represented a different investment philosophy. Rather than pursuing personal indulgence, Ellison directed focus toward comprehensive island development and infrastructure improvements benefiting Lanai’s 3,000+ residents.

Valued at approximately $500 million, this purchase established Lanai as the largest privately held island property within United States territory, featuring nearly 50 miles of pristine coastline. The island now hosts multiple Four Seasons luxury resort properties, demonstrating how private island ownership can generate hospitality revenue while maintaining environmental and community considerations. Public access to resort facilities enables visitors to experience the island’s natural splendor without private ownership.

Bonds Cay, Bahamas — The Collaborative Artist Retreat

Located 120 miles off Florida’s eastern coastline, Bonds Cay represents a unique collaborative acquisition. Performing artists Shakira, Pink Floyd’s Roger Waters, and Spanish musician Alejandro Sanz jointly purchased this 700-acre Bahamian island for $16 million. The property boasts immaculate white-sand beaches, five distinct beach areas, and three natural salt pond lakes.

The ownership trio envisioned transforming the island into an eco-conscious luxury destination and artist-focused retreat space. This acquisition reflected a creative industry trend of high-net-worth entertainment professionals investing in properties that serve dual purposes: personal enjoyment and cultural development platforms.

Investment Trends in Ultra-Luxury Island Properties

The range of most expensive private islands in the world—spanning from $16 million to $150 million—reveals distinct patterns among ultra-wealthy purchasers. Tech industry billionaires like Larry Ellison and Larry Page favored islands with development and community engagement potential. Entertainment personalities pursued either personal retreats or collaborative creative spaces. Russian oligarchs competed aggressively for historically significant properties.

These acquisitions underscore how private island ownership appeals across multiple demographics within the ultra-high-net-worth category, whether motivated by investment returns, lifestyle enhancement, environmental stewardship, or cultural legacy aspirations. As global wealth continues concentrating among elite segments, competition for exclusive island properties likely will intensify, potentially driving prices even higher in coming years.