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What else can we say about the Caribbean that you can’t get from our stunning villa pictures? Search Sheldon James’ collection of luxury villas in the Caribbean and start dreaming. 

Discover our 8 luxury villa rentals

$5,000 - $20,000/nt
La Palmeraie 1 – Asian House, Bahamas, Harbour Island
18 Guests • 9 Bedrooms • 9 Bathrooms
$5,000 - $20,000/nt
La Palmeraie 2 – Modern House, Bahamas, Harbour Island
18 Guests • 9 Bedrooms • 9 Bathrooms
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$5,000 - $28,500/nt
Sea Siren, Bahamas, Harbour Island
12 Guests • 6 Bedrooms • 5 Bathrooms
$8,500 - $15,000/nt
Nandana, Bahamas, Grand Bahama
12 Guests • 6 Bedrooms • 6 Bathrooms
$9,800 - $22,000/nt
Villa Sul Mare, Bahamas, Nassau
12 Guests • 6 Bedrooms • 7 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
$12,000 - $22,500/nt
The Beacon Hill Estate, Bahamas, Harbour Island
12 Guests • 6 Bedrooms • 9 Bathrooms
$17,500 - $24,750/nt
Villa Elan at Albany, Bahamas, Nassau
12 Guests • 6 Bedrooms • 7 Bathrooms

The islands of the Caribbean can’t be painted with one brush, but common threads include warm, white sand and cool blue water, green hills and tropical rainbow-colored drinks, sunny smiles and relaxed flip-flop vibes. Tell us what you’re looking for and we’ll find the perfect villa for your next holiday.

$35,000 - $55,000/nt
Three Bees Estate, Bahamas, Harbour Island
26 Guests • 13 Bedrooms • 13 Bathrooms

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

Don’t trust your precious time off to just anyone. Sheldon James has traveled to the Caribbean islands countless times and vetted each home and on-site partner. We will work with you before, during and after your stay to ensure that your villa stay isn’t just a vacation but an experience to remember. 

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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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: