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.
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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 399 luxury villa rentals in Caribbean
Discover our 399 luxury villa rentals
$357 - $1,215/nt
$510 - $1,200/nt
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Experienced by Our Team
$540 - $1,100/nt
Experienced by Our Team
$714 - $1,929/nt
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$742 - $2,857/nt
Villa Reviews
$795 - $2,245/nt
$795 - $2,195/nt
$825 - $3,250/nt
Experienced by Our Team
$857 - $3,286/nt
$857 - $3,857/nt
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Send us your inquiry and one of our Villa Experts will reach out as soon as possible. Or call to speak to someone immediately.
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Toll Free: 1-888-277-8882
International: +1 514-400-5151
International: +1 514-400-5151
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.
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.
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