Grand Cayman is a perfect blend of barefoot beach relaxation and island experiences, letting you decide how much or how little you want to do. Shop for luxury brands or crafts from local artisans; explore the deep historical roots of this British territory; plan a visit with its most famous residents – stingrays and turtles; or lay on the powder-soft beach all day. Ain’t life grand?
Filters
Destination
This island in the northern Caribbean is grand in every way, from its rich history and culture, to its many activities centering on the flora and fauna of the seaside and surrounding shallows, to its beaches – voted among the world’s best. Of course the luxury is grand too – let Sheldon James show you with its collection of private villa rentals on Grand Cayman.
Discover our 17 luxury villa rentals in Grand Cayman
Discover our 17 luxury villa rentals
$795 - $2,245/nt
$795 - $2,195/nt
BE IN THE KNOW Sign up for access to our private portfolio.
Pocket listings, early access, new villas and more.
VIP ACCESS STARTS HERE EXCLUSIVE ACCESS ACTIVATED Thank you and stay tuned.
Your insider news and more are on the way.
$1,095 - $2,845/nt
$1,100 - $4,000/nt
$1,145 - $3,295/nt
Villa Reviews
$1,650 - $4,950/nt
$1,750 - $9,950/nt
$1,795 - $7,995/nt
$1,950 - $4,295/nt
$1,950 - $6,750/nt
Ready to go?

So are we.
Send us your inquiry and one of our Villa Experts will reach out as soon as possible. Or call to speak to someone immediately.
Inquire now
Toll Free: 1-888-277-8882
International: +1 514-400-5151
International: +1 514-400-5151
THE SHELDON JAMES WAY
When it comes to your holidays, don’t leave anything to chance. Sheldon James will treat your time spent away with family and friends as a precious commodity, ensuring it is memorable from start to finish. From choosing the perfect group villa to building an itinerary that suits your group perfectly, it’s the Sheldon James way.
Our guest-first focus
You’re always our top priority–we’ve got you covered on all your travel needs before, during and after your stay.
Hand-selected villas
Our standards are high. Each and every villa we offer has been visited or thoroughly reviewed by a member of our team.
A trusted network
We only work with partners we know and trust, so you can count on them to reflect our values and standards.
Our mission is to transform our experience and relationships into a unique offering for you.
explore the world
We have much more than you see here. Want to escape to Thailand or an exclusive villa in Mykonos? We can do that.
Internal Info
Internal Info