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Beaches, mountains and everything in between – where would you like to lay your head, kick up your feet, and raise a glass?  Sheldon James’ luxury villa rentals span thousands of miles, but all offer a unique way to experience our world in comfort and privacy. We’ll work with you to find the perfect spot then, along with our trusted partners, take your holiday experience to the next level with curated experiences and top-notch services.

Sheldon James’ luxury villa rentals span thousands of miles, but all offer a unique way to experience our world in comfort and privacy. 

Discover our 904 luxury villa rentals

$1,100 - $4,000/nt
(INACTIVE) Les Jalousies, Grand Cayman, Cayman Kai
8 Guests • 3 Bedrooms • 4 Bathrooms
Rates upon request
2 Bdr Beach House at Parrot Cay, Turks and Caicos, Parrot Cay
4 Guests • 2 Bedrooms • 2 Bathrooms
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Villa Reviews

  • Solara, Turks and Caicos

    Jeff Miller, July 2024

  • Hokulani 825, Hawaii

    Trip was wonderful and the accommodates met our high expectations. James and team did a nice job
    communicating and providing details.

    Ben, February 2025

  • Wind Chime Villa, Turks and Caicos

    Spectacular villa. Perfectly designed. Immaculately maintained. Unbelievably attentive staff. One of the best we’ve had the good fortune to enjoy.

    Greg H, February 2024

  • Villa Agama, St. Martin

    Beautiful villa and view, great service, great recommendation from Wade!

    Gian Carlo D., April 2025
$2,600 - $10,000/nt
4BR Puka Pa Estate at Four Seasons Hualalai Resort, Hawaii, Big Island
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$3,800 - $14,000/nt
5BR Estate Home at Mauna Kea Resort, Hawaii, Big Island
10 Guests • 5 Bedrooms • 5 Bathrooms
$3,600 - $10,000/nt
5BR Fairways North at Mauna Kea Resort, Hawaii, Big Island
10 Guests • 5 Bedrooms • 7 Bathrooms
$5,280 - $8,000/nt
A La Mer, St. John, Great Cruz Bay
14 Guests • 7 Bedrooms • 7 Bathrooms
Recently Booked
$3,750 - $20,500/nt
Aama, Barbados, Sandy Lane
14 Guests • 7 Bedrooms • 8 Bathrooms
$1,700 - $3,150/nt
Abacus, Jamaica, Montego Bay
8 Guests • 4 Bedrooms • 4 Bathrooms
€9,383 - €38,633/nt
Adeline, France, Paris
8 Guests • 4 Bedrooms • 4 Bathrooms
€2,250 - €3,000/nt
Adorna, Italy, Tuscany
14 Guests • 7 Bedrooms • 7 Bathrooms

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.

Thank you for contacting us!

A Villa Expert will be in touch with you shortly. If you want to speak to someone immediately, please give us a call.

Toll Free: 1-888-277-8882
International: +1 514-400-5151

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