All Villas

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 831 luxury villa rentals

Rates upon request
2 Bdr Beach House at Parrot Cay, Turks and Caicos, Parrot Cay
4 Guests • 2 Bedrooms • 2 Bathrooms
$2,600 - $10,000/nt
4BR Puka Pa Estate at Four Seasons Hualalai Resort, Hawaii, Big Island
8 Guests • 4 Bedrooms • 4.5 Bathrooms
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Villa Reviews

  • Villa Embrace, St. Barts

    Embrace St Barts exceeded our expectations. The view and sunsets were beyond amazing. The home was impeccably designed, inviting and comfortable THE ARTWORK amazing. Dorian was so helpful to be sure we experienced all the island had to offer....

    Carol W, March 2024

  • Aqua Dream, St. Martin

    The staff were Excellent,very knowledgeable and professional.My Experience was Excellent looking forward doing business again.

    Vernon M, March 2024

  • Villa Las Rocas, Los Cabos

    We’ve been using Sheldon James for all of our villa rentals and this was yet another perfect experience! The team really knows what they’re doing and always find the perfect villa for our events.

    Norm L, June 2023

  • Ani Dominican Republic, Dominican Republic

    Once again, James has thought about everything my family is looking for in a Villa vacation. We had an amazing family vacation that exceeded our expectations. The Villa was beyond our imagination. It was pristine. The Staff was impeccable. They...

    Debbie A, July 2024
$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
$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
€2,000 - €2,300/nt
Adria, Italy, Lake Como
8 Guests • 4 Bedrooms • 4 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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