Jamaica
Filters
Nightly budget
$
$ +
Amenities

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
Experienced by Our Team
$1,600 - $4,800/nt
Sweet Spot, Jamaica, Runaway Bay
12 Guests • 6 Bedrooms • 6 Bathrooms
BE IN THE KNOW
Sign up for access to our private portfolio.
Pocket listings, early access, new villas and more.
VIP ACCESS STARTS HERE
EXCLUSIVE ACCESS ACTIVATED
Thank you and stay tuned.
Your insider news and more are on the way.
$1,700 - $3,150/nt
Abacus, Jamaica, Montego Bay
8 Guests • 4 Bedrooms • 4 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 Bathrooms
Villa Reviews

  • Nevaeh, Anguilla

    Wade chose an amazing villa for us. This is the second time using him and he has been spot on each time. Tania was super helpful and everything was arranged perfectly and her recommendations were great. I thought the staff...

    Greg P., December 2025

  • Villa Azetes, St. Barts

    Loved it! Excellent work to get the two villas near each other. cleaning people were great. Loved the food they brought us

    David K, December 2025

  • Villa Cascade, Turks and Caicos

    Villa Cascade was the most luxurious place I have stayed in so far and has now set the bar for my family and I. Everywhere I looked there was something beautiful, comfortable, and thoughtfully designed. The staff was absolutely incredible....

    Katie, January 2026

  • Villa Cascade, Turks and Caicos

    10 stars rating!! It was the most luxurious place I have ever stayed in, and I loved walking out my bedroom door each morning to see my swimming pool.
    The staff was incredible, and made me feel like a queen....

    Jessi, January 2026
$2,000 - $3,285/nt
BougainVilla, Jamaica, Montego Bay
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,200 - $4,000/nt
Villa Rosa, Jamaica, Montego Bay
11 Guests • 4 Bedrooms • 6 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
$2,429 - $5,000/nt
Flower Hill, Jamaica, Montego Bay
16 Guests • 6 Bedrooms • 14 Bathrooms
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

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.

Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL:

Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL:

Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL: