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
Sea Biscuit, Jamaica, Ocho Rios
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,558 - $2,858/nt
Villa Rosa, Jamaica, Montego Bay
11 Guests • 4 Bedrooms • 6.5 Bathrooms
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Villa Reviews

  • 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

  • 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
Experienced by Our Team
$1,600 - $4,800/nt
Sweet Spot, Jamaica, Runaway Bay
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$1,700 - $3,150/nt
Abacus, Jamaica, Montego Bay
8 Guests • 4 Bedrooms • 4 Bathrooms
$1,700 - $3,285/nt
BougainVilla, Jamaica, Montego Bay
12 Guests • 6 Bedrooms • 6 Bathrooms
Experienced by Our Team
$1,700 - $3,800/nt
Four Winds, Jamaica, Ocho Rios
10 Guests • 5 Bedrooms • 5 Bathrooms
$1,900 - $4,400/nt
Hidden Bay, Jamaica, Runaway Bay
12 Guests • 6 Bedrooms • 6.5 Bathrooms
Experienced by Our Team
$2,429 - $5,000/nt
Flower Hill, Jamaica, Montego Bay
16 Guests • 6 Bedrooms • 14 Bathrooms

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
$2,500 - $6,200/nt
Indigo (formerly Greatview), Jamaica, Montego Bay
20 Guests • 10 Bedrooms • 10 Bathrooms
Experienced by Our Team
$2,858 - $5,715/nt
Amanoka, Jamaica, Discovery Bay
14 Guests • 7 Bedrooms • 8 Bathrooms
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.

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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