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 394 luxury villa rentals

$357 - $1,215/nt
Casa Capriolo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
$510 - $1,200/nt
Villa Madinina, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3 Bathrooms
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Villa Reviews

  • Round Rock Estate, Anguilla

    Neil O, December 2024

  • Sugar Kube, Turks and Caicos

    It was an amazing Villa loved every moment of our honeymoon. The staff were amazing they provided such a great service from Housekeeping to our 2 masseuse Melanie and Marie and your chefs Juan and Emara, Great food. We will...

    Luis R, December 2024

  • Wind Chime Villa, Turks and Caicos

    Excellent trip as always! We love working with Sheldon James, they are always there when you need them and making the process so easy. Our family of 5 has been working with the company for years and have always...

    Julie B, December 2024

  • Tip of the Tail, Turks and Caicos

    Overall, the villa and the staff were a big hit with the family!!   I would give the trip a solid ‘A’ score due to the home, location and staff.   Everyone was very pleased. The house was good for my family...

    Jenny M, February 2025
Experienced by Our Team
$540 - $1,100/nt
Sugar Kube, Turks and Caicos, Turtle Cove
2 Guests • 1 Bedrooms • 1.5 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 - $2,245/nt
Sea 2 Infinity, Grand Cayman, Cayman Kai
8 Guests • 4 Bedrooms • 4 Bathrooms
$795 - $2,195/nt
Tarasand, Grand Cayman, Cayman Kai
8 Guests • 4 Bedrooms • 3 Bathrooms
$825 - $3,250/nt
Giselle, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 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.

Experienced by Our Team
$857 - $3,286/nt
Ambiance, St. Martin, Terres Basses
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$857 - $3,857/nt
Casa Roc, St. Barts, Gustavia
6 Guests • 3 Bedrooms • 3 Bathrooms
THE SHELDON JAMES WAY

Don’t trust your precious time off to just anyone. Sheldon James has traveled to the Caribbean islands countless times and vetted each home and on-site partner. We will work with you before, during and after your stay to ensure that your villa stay isn’t just a vacation but an experience to remember. 

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 focusHand-select villasA 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.

Thank you for contacting us!

A Villa Expert will be in touch with you shortly. If you want to speak to someone immediately, please give us a call.

Toll Free: 1-888-277-8882
International: +1 514-400-5151

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