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 345 luxury villa rentals

$357 - $1,215/nt
Casa Capriolo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
Experienced by Our Team
$540 - $1,100/nt
Sugar Kube, Turks and Caicos, Turtle Cove
2 Guests • 1 Bedrooms • 1.5 Bathrooms
BE IN THE KNOW
Sign up for access to our private portfolio.
Pocket listings, early access, new villas and more.
VIP ACCESS STARTS HERE

Name*
This field is for validation purposes and should be left unchanged.
EXCLUSIVE ACCESS ACTIVATED
Thank you and stay tuned.
Your insider news and more are on the way.
Villa Reviews

  • Ani Dominican Republic, Dominican Republic

    Once again, James has thought about everything my family is looking for in a Villa vacation. We had an amazing family vacation that exceeded our expectations. The Villa was beyond our imagination. It was pristine. The Staff was impeccable. They...

    Debbie A, July 2024

  • Cabuya, Turks and Caicos

    From the initial enquiry, James and his team were exceptional, responsive and organised. James helped us find the Villa that suited our taste and needs, and was patient while we reviewed each one and finally made a decision (recommended by...

    Alyssa R, July 2024

  • Solara, Turks and Caicos

    Jeff Miller, July 2024

  • Aqua Dream, St. Martin

    The staff were Excellent,very knowledgeable and professional.My Experience was Excellent looking forward doing business again.

    Vernon M, March 2024
$685 - $2,645/nt
Villa Allegra, St. Martin,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
Experienced by Our Team
$714 - $1,929/nt
Bamboo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2.5 Bathrooms
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$742 - $2,857/nt
Just in Paradise, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3 Bathrooms
$795 - $2,300/nt
Sea 2 Infinity, Grand Cayman, Cayman Kai
8 Guests • 4 Bedrooms • 4 Bathrooms
$825 - $3,250/nt
Giselle, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 5 Bathrooms
Experienced by Our Team
$857 - $3,286/nt
Ambiance, St. Martin, Terres Basses
8 Guests • 4 Bedrooms • 4.5 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.

$857 - $3,430/nt
Palm Bay, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 5.5 Bathrooms
Experienced by Our Team
$857 - $2,500/nt
Lotus, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3.5 Bathrooms