Simply Islands

Luxury Living
Island Style

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.

Jill · Founder

A note from our founder

Every villa on Simply Islands has been chosen because someone on our team has been there — stood in it, swum from it, or eaten at a table there.

I’ve spent 25 years getting to know these islands — not as a tourist, but as someone who has come to understand what makes each one particular. We work with a carefully selected network of local teams who share our values and our standards, because great service can’t be delivered from a distance.

We don’t list villas we haven’t seen. We don’t make promises we can’t keep. And when something isn’t right, you speak to someone who knows the property and can fix it.

Jill

Founder & Director · Simply Islands

Read our story

What they say

From our guests

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

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

Canada

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