New Home - Simply Islands : Simply Islands

Luxury villa rentals are some of the most elegant properties

Choose from hundreds of private estates boasting acres of manicured indoor and outdoor spaces complete with tailored hospitality services upon request. At Simply Islands, we deliver unique and memorable stays every time. Let us take care of the details - sit back, relax, and enjoy paradise.

Featured Stays

Acai

Nestled near Flamands beach, ACAI villa exudes luxury across three levels. With its classic colonial design, contemporary living spaces, and lush gardens, it offers a tranquil escape with breathtaking ocean views.

Acamar

Luxury Villa St. Barth - Acama is nestled on a hillside in the tranquil Toiny district, the villa provides a serene escape from the everyday. With a design that marries contemporary aesthetics with local architectural elements.

Acropolis

Acropolis, a newly refurbished holiday rental in Colombier, Saint-Barths, offers an affordable and family-friendly option for Caribbean vacations. With its contemporary design, the villa provides a cozy and peaceful haven in the heart of the Caribbean.

Alila

Alila is a luxury private estate, designed by architect Michael Gomes and is themed with Balinese-inspired elements in earthy hues with pops of colour in the bedrooms.

Amor View

In the heart of St. Barths, Amor View welcomes up to eight guests in utmost luxury, offering a stunningly beautiful panoramic view.

Villa America

Contemporary Mustique Villa America, a stylish open plan villa embracing outdoor living with spectacular views over the Grenadines.

Hemingway House

Hemingway House Barbados, located between Gibbes Beach and Mullins Beach overlooks the Caribbean ocean.

Sandrock

Sandrock in Bequia, beachfront living in this supurb unique property, enjoy sunrise and sunset over two oceans.

Presenting: Simply Islands

Simply Islands ensures exquisite experiences every time with diligent and comprehensive care of our properties and our guests. We are proud to offer a diverse and expansive array of luxury villas meant to not only meet our guests’ needs, but to exceed their expectations.

What they say...

Average customer rating: 4.8/5

In my 25+ years of exploring the Caribbean I’ve learned that the most unspoiled and idyllic places, the ones I most love, are typically the hardest to get to and to find… Bequia is one of those islands you wish you could be the last to discover! Having had the good fortune to enjoy every manner of breathtaking Caribbean villas over the years, I can tell you without hesitation that Retreat House is not only without peer on Bequia, it is hands down my all time favorite Caribbean villa… I don’t say that lightly, but Retreat House simply has it all! If you’re still reading, stop! Reach out to Jill! Book your dates… just don’t tell anyone else, trust me, you’ll want to be the last one to discover this magical paradise 😉 – Retreat House

Matt Louderback

At risk of understatement our party were high maintenance with unusual needs and complex requirements. Jill and her incredible team, both in her office and in the villa, sailed through the entire 6 weeks with aplomb and most importantly good humour. I cannot recommend Jill and Simply Islands too highly. We will definitely use again when we return to the Caribbean. – Hemingway House

Ian, Singapore

Ceiba villa was extremely comfortable with a lovely helpful household team who could not have been more delightful. We would happily return. – Ceiba

Heather, London

Loved our stay at Gatehouse at Pavilion Grove. Great location to beach and Holetown. Staff are very friendly and accommodating. This would definitely be a place I would rent again. – Gatehouse at Pavilion Grove

Margret, Canada

Luxury Villas, Exceptional Care, Exquisite Experiences.

Luxury villa rentals are some of the most elegant properties

Featured Stays