Jamaica

There’s something special about Jamaica. The lush tropical feel, warm melting pot culture, groovy reggae vibes that can transport you in a few notes. Sheldon James gets it – now let’s get you there in style with our collection of luxury villa rentals tucked across the island’s best hideaways, from Montego Bay to Ocho Rios.

Discover our 18 luxury villa rentals

$1,330 - $1,475/nt
$1,558 - $2,858/nt
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Experienced by Our Team
$1,600 - $4,800/nt
$1,700 - $3,150/nt
$1,700 - $3,285/nt
Villa Reviews
  • Sunset Point, Turks and Caicos

    I have worked with James on many Villa vacations over the past 8 years. They are always exceptional. James has learned what my family is looking for in a holiday and is very particular in which Villa’s he sends...

    Debbie A, March 2025
  • Villa Lorenne, Dominican Republic

    What a dream vacation!! The villa is beautiful. The staff was phenomenal. Our celebrations were so special. No one wanted to leave!!!

    Sima I, April 2025
  • Villa Agama, St. Martin

    Beautiful villa and view, great service, great recommendation from Wade!

    Gian Carlo D., April 2025
  • Round Rock Estate, Anguilla

    Neil O, December 2024
Experienced by Our Team
$1,700 - $3,800/nt
$1,900 - $4,400/nt

Beaches? Got ‘em. Watersports? Endless. Food? Bountiful. Culture, shopping, nightlife – it’s all here in Jamaica, a diverse island waiting to be explored. Choose your own adventure each time with our portfolio of luxury villa rentals in Jamaica.

Experienced by Our Team
$2,429 - $5,000/nt
Experienced by Our Team
$2,500 - $6,200/nt
Experienced by Our Team
$2,858 - $5,715/nt

Ready to go?

So are we.

Send us your inquiry and one of our Villa Experts will reach out as soon as possible. Or call to speak to someone immediately.
Inquire now
Toll Free: 1-888-277-8882
International: +1 514-400-5151
THE SHELDON JAMES WAY

We wouldn’t settle for anything but perfection – why should you? Travel with Sheldon James and be secure in the knowledge that your Jamaica villa vacation is being handled by people that have been there, done that, taken all the notes. Let us show you how to experience a villa our way!

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.