Caribbean
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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 468 luxury villa rentals

Experienced by Our Team
$3,785 - $13,500/nt
Baraka Point, Virgin Gorda, Nail Bay
16 Guests • 6 Bedrooms • 6 Bathrooms
Experienced by Our Team
$8,450 - $24,000/nt
Footprints, Turks and Caicos, Grace Bay
16 Guests • 8 Bedrooms • 8 Bathrooms
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$357 - $1,215/nt
Casa Capriolo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
Experienced by Our Team
$540 - $1,100/nt
Sugar Kube, Turks and Caicos, Turtle Cove
2 Guests • 1 Bedrooms • 1 Bathrooms
Experienced by Our Team
$714 - $1,929/nt
Bamboo, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
Villa Reviews

  • Amandara, St. Martin

    The villa was fantastic, spacious and well kept. Everyone found the experience unique. We did not want to go out, we had everything we needed including sports and entertainment. Chef Tim was incredible, really attentive and aware of everybody’s taste,...

    Carole G, February 2026

  • Twin Palms Villa, Turks and Caicos

    The house was unbelievable and the staff and chef were incredible. Everyone was so nice. Whatever we needed all day and night we got as soon as we requested and everyone was so happy. Kids loved it! Location was great...

    Ally V., March 2026

  • Casa Minitas, Dominican Republic

    Great working with Alba who was attentive and prompt for each follow up.

    Marco, February 2026

  • Sea 2 Infinity, Grand Cayman

    This was our third visit to Grand Cayman, and this time we stayed for two wonderful weeks (+ 3 extra days due to bad weather at home) at Sea 2 Infiniti in Rum Point. What a beautiful home! From the...

    Debbie W., January 2026
$715 - $1,886/nt
Nid D’Amour, St. Martin, Terres Basses
4 Guests • 2 Bedrooms • 2 Bathrooms
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$742 - $2,857/nt
Just in Paradise, St. Martin, Terres Basses
6 Guests • 3 Bedrooms • 3 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.

$795 - $2,245/nt
Sea 2 Infinity, Grand Cayman, Cayman Kai
8 Guests • 4 Bedrooms • 4 Bathrooms
$795 - $2,195/nt
Tarasand, Grand Cayman, Cayman Kai
8 Guests • 4 Bedrooms • 3 Bathrooms
$825 - $3,572/nt
Giselle, St. Martin, Terres Basses
10 Guests • 5 Bedrooms • 5 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

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:

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