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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 6 luxury villa rentals

$1,330 - $1,475/nt
Sea Biscuit, Jamaica, Ocho Rios
6 Guests • 3 Bedrooms • 3 Bathrooms
Experienced by Our Team
$1,700 - $3,800/nt
Four Winds, Jamaica, Ocho Rios
10 Guests • 5 Bedrooms • 5 Bathrooms
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$3,600 - $7,500/nt
Promiseas, Jamaica, Ocho Rios
16 Guests • 8 Bedrooms • 8 Bathrooms
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$4,000 - $5,900/nt
Canoe Cove, Jamaica, Ocho Rios
14 Guests • 7 Bedrooms • 7.5 Bathrooms
$4,400 - $5,500/nt
Buttonwood Reef, Jamaica, Ocho Rios
12 Guests • 6 Bedrooms • 6.5 Bathrooms
Villa Reviews

  • Maison de Cortes, Los Cabos

    The home was truly amazing, the staff was friendly and polite. The chef we had made amazing food and the group couldn’t have been happier. This was the best house we have stayed at in Cabo with great build...

    Fabio C, November 2024

  • Casa Familia, Punta Mita

    The house was great! Beautiful grounds and really nice beach below. The staff was excellent. Reminded me of the 6 star service you get on a yacht charter. Helen was wonderful as always. Will definitely consider booking again in the...

    Greg P., December 2024

  • Founders Villa, Dominican Republic

    James, who I have been working with for many years on our annual family vacations, is great to work with and he always gives me great properties. The Villa is exceptional and services five star.

    Alan M., May 2025

  • Baraka Point, Virgin Gorda

    My family has a great time and Wade was a true professional. The trip was everything Wade said it would be. The staff on Baraka Point was unreal and made me and my family feel very comfortable. and a...

    Zachary Z, November 2023
Experienced by Our Team
$4,428 - $8,500/nt
Malatai, Jamaica, Ocho Rios
16 Guests • 8 Bedrooms • 8 Bathrooms

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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.

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