Grand Cayman

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

$795 - $2,300/nt
Sea 2 Infinity, Grand Cayman, Cayman Kai
8 Guests 4 Bedrooms 4 Bathrooms
$950 - $1,950/nt
Tarasand, Grand Cayman, Cayman Kai
8 Guests 4 Bedrooms 3 Bathrooms
$1,100 - $4,000/nt
Les Jalousies, Grand Cayman, Cayman Kai
8 Guests 3 Bedrooms 4 Bathrooms
$1,150 - $3,750/nt
Cayman Castle, Grand Cayman, East End
12 Guests 5 Bedrooms 5.5 Bathrooms
$1,500 - $3,650/nt
Olympus, Grand Cayman, Cayman Kai
12 Guests 4 Bedrooms 5.5 Bathrooms
$1,850 - $4,250/nt
Kaiku, Grand Cayman, Cayman Kai
15 Guests 7 Bedrooms 6.5 Bathrooms

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?

$1,895 - $4,695/nt
Villa Mora, Grand Cayman, South Sound
18 Guests 7 Bedrooms 7.5 Bathrooms
$1,950 - $4,250/nt
Moon Kai, Grand Cayman, Cayman Kai
14 Guests 6 Bedrooms 6 Bathrooms
$1,950 - $6,752/nt
Evolution, Grand Cayman, Bodden Town
18 Guests 7 Bedrooms 7.5 Bathrooms
$2,450 - $8,950/nt
Bella Roca, Grand Cayman, East End
22 Guests 8 Bedrooms 10 Bathrooms
$2,950 - $5,850/nt
Fischers Reef, Grand Cayman, Cayman Kai
20 Guests 8 Bedrooms 8.5 Bathrooms
$2,950 - $7,948/nt
Kaia Kamina, Grand Cayman, Cayman Kai
18 Guests 7 Bedrooms 9 Bathrooms

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.
Client-first focus Hand-select villas A trusted network

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.