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 353 luxury villa rentals

$325 - $4,600/nt
The One at The St. James, Barbados, Paynes Bay
8 Guests • 4 Bedrooms • 5 Bathrooms
$357 - $1,215/nt
Casa Capriolo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
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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
Experienced by Our Team
$540 - $1,100/nt
Sugar Kube, Turks and Caicos, Turtle Cove
2 Guests • 1 Bedrooms • 1.5 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 - $2,500/nt
Lotus, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3.5 Bathrooms
Experienced by Our Team
$857 - $3,500/nt
Mer Soleil, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 5.5 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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