Secluded Private Island Rentals. Expertly Picked, Personally Serviced

Sienna Charles' ultra-high-net-worth members enjoys exclusive access to the most gorgeous hidden tropical islands in the world. From waking up in a serene oasis to spending evenings with family in luxurious tranquility, our luxury travel concierge services deliver the private island rental experience fully tailored and serviced for our members to simply enjoy.

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Coveted Corners of the World




Bora Bora





Sienna Charles personally vets every restaurant, spa, hotel and experience before offering them to clients, which partly explains a customer pool that ranges from CEOs and bankers to George W. Bush and his family.

Unearth Your Oasis with Luxurious Private Island Rentals

Our discerning clientele deserves an escape from the everyday, and Sienna Charles delivers. Our unparalleled luxury private island rental experiences transport ultra-high-net-worth individuals out of the commotion of daily life and into a private oasis of tranquility. From tucked-away villas that offer incredible views to endless stretches of flawless white sand that dissolve into sparkling cerulean waters, our private island vacation rentals are the ideal way to relax and rejuvenate in unparalleled luxury.

With a Sienna Charles private island rental, our members enjoy every luxury amenity, while experiencing the exhilaration of a secluded tropical vacation surrounded by the comforts of home. Renting an island is a perfect setting for an unforgettable romantic honeymoon, an exclusive getaway or entertaining family and friends.

The Sienna Charles ultimate luxury travel experience doesn’t end at simply renting an island for vacation. We also provide white-glove service throughout the entire stay, from securing private transportation to the island to providing personal butlers, chefs and other concierge services. Backed by the strong relationships we have built with private islands around the globe, along with the experience and knowledge of our team, no desire is unattainable and no destination is unreachable. An exclusive escape from everyday life awaits.

All-Inclusive Life Meets Unparalleled Luxury

Private Villas

Our private villa rentals are unsurpassed in luxury, amenities and discretion. From admiring stunning views of lush tropical foliage or expansive beaches to floating in immaculate private infinity pools, our guests enjoy unparalleled splendor and absolute seclusion.

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Luxury Dining

Included with a luxury private island rental is access to a private chef who can curate a personalized menu complete with every delicacy our guests desire. Each course is meticulously crafted from the finest fresh ingredients and perfectly paired with premier vintage wines. Enjoy fine dining al fresco surrounded by lush tropical beauty and some of the world’s most stunning views.

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World-Class Experiences

Renting an island for vacation wouldn’t be complete without exclusive access to extraordinary amenities such as private helicopter tours, yacht charters, private yoga sessions and spa treatments. By understanding our members’ desires, we are able to meticulously curate a unique experience that exceeds expectations.

Transportation Arrangements

Sienna Charles members travel in ultimate luxury from the beginning to the end of every trip. Whether the journey to their tropical paradise takes place on a private aircraft, a luxury yacht or a personal boat, our guests arrive and depart in modern comfort and style, with every amenity included.

Reserve Luxurious Private Islands

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Founded by a Connoisseur of Luxury and Exclusive Travel Experiences

Sienna Charles brings the most exclusive luxury experiences to our members through the world-class knowledge and lived experiences of our founder, Jaclyn Sienna India. Backed by her eye for the exquisite, exceptionally refined palate, commitment to quality and deep understanding of personal desires, Jaclyn spends more than 200 days on the road annually and has traveled to more than 90 countries in an exhaustive search to unearth the world’s most unique and exclusive luxury experiences.

Using the resources and destinations she discovers in her quest, she curates remarkable and one-of-a-kind moments for our members. Jaclyn’s determination and uncompromising dedication to delivering the finest things in life have led her to become a trailblazer and preeminent authority in the luxury travel industry.

She is also well-respected by proprietors in the industry who own some of the world’s most luxurious, high-class islands and properties. These relationships become part of her prestigious little black book, which, along with her ability to connect clients’ desires with ideal destinations, has enabled Sienna Charles to become the premier luxury travel concierge for ultra-high-net-worth individuals.

From sipping an icy cocktail on the deck of a private villa rental overlooking a pristine white sand beach to sailing across crystal clear waters aboard a chartered luxury yacht, every moment of our guests’ experience is one of a kind. Sienna Charles delivers an unbounded life of inimitable luxury.

Your Questions, Answered

For discerning clientele seeking a peaceful and tranquil getaway, renting an island for a week is the ideal option. A private island rental not only provides unparalleled privacy and effortless relaxation, but it is also a perfect way to create a custom vacation tailored to specific desires. Our members receive access to a personal chef, five-star catering services and other premier amenities just steps away from white sand beaches and crystal clear blue waters. Renting an island for vacation is the ultimate way to enjoy a secluded tropical oasis with all the comforts of home.

The Sienna Charles private island vacation rental service delivers an all-inclusive tropical getaway surrounded by awe-inspiring scenery and unexplored sanctuaries. Whether our members wish to stay in an intimate oasis in the Caribbean or a secluded oceanside villa in Southeast Asia, our private island vacation rentals meet any desire and exceed every expectation. Our luxury travel concierge will meticulously handle every detail from transportation to amenities so that our members can simply relax and enjoy their well-deserved getaway.

Our members have unlimited 24/7 text or email access to our luxury travel concierge team. Simply reach out and we will provide options for private island rentals that meet any desire. Once a selection has been made, our team will meticulously handle every detail, from private jet charters or other transportation to securing any additional experiences. We plan and execute every moment of the vacation with impeccable attention to detail to ensure that our discerning clientele can relax and enjoy a seamless experience from start to finish.

A private island is an unparalleled luxury travel destination, but reaching the perfect tropical paradise can be challenging. Sienna Charles has exclusive access to the best luxury transportation options, such as private jets, yachts, boats, helicopters and seaplanes. Members who wish to savor the journey, especially those who love sailing and adventure, may choose a luxury yacht charter or boat as their preferred mode of transportation. For members who would prefer to arrive quickly, a helicopter or private jet charter is a swift and luxurious option, especially when landing on larger islands with private airstrips. However, small private islands do not always have landing strips to accommodate helicopters. A private seaplane is the perfect combination of sea and air travel that offers an adventurous way to reach a secluded island. Transportation options vary by island, but Sienna Charles will always secure the most luxurious mode of transportation that meets our members’ needs.

While we are able to satisfy even last-minute requests, Sienna Charles appreciates when members contact us as soon as they make travel decisions. Once we receive a text or email, our travel concierge starts researching destinations that meet the stated desires and within 24 hours, we will offer a curated list of exciting options to choose from. After the details have been confirmed via email or text, a direct payment can be completed.

Renting a private island is a personal choice for our discerning clientele, with limitless options for the length of stay. Many members wish to savor their escape from the ordinary and allow enough time to truly relax and enjoy the lush tropical serenity. Other members may want a quick getaway that still provides the opportunity to recharge and rejuvenate. Whether a member wishes to rent an island for a week or more, or simply a few days, Sienna Charles will curate an unforgettable experience.

Sienna Charles impeccably plans every detail to ensure a seamless experience. But if unforeseen circumstances arise, we are available to assist via text or email, 24/7. We will work to resolve the issue as quickly and efficiently as possible to allow our members to get back to enjoying their tropical getaway.

A Sienna Charles membership begins at $75,000 annually and includes all luxury private villa or 5-star hotel bookings, trip planning for one-of-a-kind getaways, reservations at the most highly sought-after fine dining and Michelin star restaurants, VIP access to the world’s most coveted events and 24/7 luxury concierge services.

Our membership is open to individuals who are a perfect match for our premier travel concierge services. After a potential member completes our online application, our team will reach out to schedule an interview with our founder, Jaclyn Sienna India. We welcome the opportunity to cater to a new client’s needs by selecting luxury travel experiences, elite restaurant bookings and secluded private island stays that perfectly match their every desire.

Tropical Tranquility Awaits with Sienna Charles