Caribbean

What else can we say about the Caribbean that you can’t get from our stunning villa pictures? Search Sheldon James’ collection of luxury villas in the Caribbean and start dreaming. 

Discover our 271 luxury villa rentals

$400 - $2,000/nt
Casa Capriolo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
$540 - $1,100/nt
Sugar Kube, Turks and Caicos, Turtle Cove
2 Guests • 1 Bedrooms • 1.5 Bathrooms
$714 - $1,929/nt
Bamboo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2.5 Bathrooms
$742 - $2,857/nt
Just in Paradise, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3 Bathrooms
$785 - $3,857/nt
Villa Les Palmiers Bleu, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 6 Bathrooms
$786 - $2,357/nt
Lotus, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3.5 Bathrooms

The islands of the Caribbean can’t be painted with one brush, but common threads include warm, white sand and cool blue water, green hills and tropical rainbow-colored drinks, sunny smiles and relaxed flip-flop vibes. Tell us what you’re looking for and we’ll find the perfect villa for your next holiday.

$795 - $2,300/nt
Sea 2 Infinity, Grand Cayman, Cayman Kai
8 Guests • 4 Bedrooms • 4 Bathrooms
$814 - $2,286/nt
Grand Palms, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3.5 Bathrooms
$821 - $3,214/nt
Giselle, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 5 Bathrooms
$857 - $3,429/nt
Villa Abby, St. Barts, Vitet
6 Guests • 3 Bedrooms • 3 Bathrooms
$857 - $3,857/nt
Casa Roc, St. Barts, Gustavia
6 Guests • 3 Bedrooms • 3 Bathrooms
$875 - $3,450/nt
Villa Wellness, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 5 Bathrooms