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 334 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
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Villa Reviews

  • 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

  • Mes Amis, St. Martin

    An experience truly unimaginable. Our villa, Mes Amis was a resort on its own. Although we were only a family of 10 celebrating a very special birthday, our villa was one of the, if not the largest in Terre...

    Stewart R, March 2024

  • Beach Enclave GB Oceanview Villa 6bdr, Turks and Caicos

    We had a great experience at beach enclave. 5 star property and service. The only confusion was at first when the villa number/size was slightly different than what we thought we signed up for, but nonetheless we had a...

    Matt P, February 2023

  • Just in Paradise, St. Martin

    Wade with Sheldon James was exceptional to work with. Everything was perfect!

    Lelah P, June 2024
$672 - $2,286/nt
Grand Palms, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3.5 Bathrooms
$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

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 - $3,429/nt
Villa Abby, St. Barts, Vitet
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

Vic Tool

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

Internal Info

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

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