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.
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 15 luxury villa rentals in Jamaica
Discover our 15 luxury villa rentals
$1,330 - $1,475/nt
Sea Biscuit, Ocho Rios, Jamaica
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,558 - $2,858/nt
Villa Rosa, Montego Bay, Jamaica
11 Guests • 4 Bedrooms • 6.5 Bathrooms
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$1,600 - $4,800/nt
Sweet Spot, Runaway Bay, Jamaica
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$1,700 - $3,800/nt
Four Winds, Ocho Rios, Jamaica
10 Guests • 5 Bedrooms • 5 Bathrooms
$1,700 - $3,285/nt
BougainVilla, Montego Bay, Jamaica
12 Guests • 6 Bedrooms • 6 Bathrooms
$1,900 - $4,400/nt
Hidden Bay, Runaway Bay, Jamaica
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$2,429 - $5,000/nt
Flower Hill, Montego Bay, Jamaica
16 Guests • 6 Bedrooms • 14 Bathrooms
$2,500 - $6,200/nt
Indigo (formerly Greatview), Montego Bay, Jamaica
20 Guests • 10 Bedrooms • 10 Bathrooms
$2,858 - $5,715/nt
Amanoka, Discovery Bay, Jamaica
14 Guests • 7 Bedrooms • 8 Bathrooms
$3,100 - $6,600/nt
Fortlands Point, Discovery Bay, Jamaica
18 Guests • 9 Bedrooms • 9 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.
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.
