Kauai

What more is there to say about Hawaii? This quintessential getaway should be experienced with the five senses, and Sheldon James villas offer a luxurious indoor-outdoor headquarters from which to explore the island paradise. Come with us and see how we deliver the aloha spirit with style.

Discover our 7 luxury villa rentals

$1,260 - $5,000/nt
$1,300 - $4,500/nt
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.
Villa Reviews
  • Dolphin Manor, Hawaii

    Great house, as advertised. Nicely furnished. Pool is smaller than I thought from the pictures, but I should have looked more carefully. Activities and arranged chef were wonderful. The outreach from the concierge distinguished SJ and was much appreciated.

    Dave B., December 2025
  • Maui Ocean Breeze, Hawaii

    The property, as always, was very comfortable and enjoyable. We had been apprehensive about returning to Maui in light of the fire that had destroyed much of Lahaina, but it really did not impact our visit. Kapalua, Ka’anapali, and...

    Jim P, September 2024
  • The Resort, Spain

    The Sheldon James team knocked it out of the park again for our annual trip. We are typically confirming late into the rental season but Wade and his team always comes through with a great rental property for our large...

    Hillary Fujii, June 2024
  • Casa Napa, Riviera Maya

    Remarkable property that exceeds expectations in almost every way… start with location… the deck is literally a stones throw from the water…. Impeccably designed and maintained landscape, including plenty of coconuts… we asked Emilio to cut a couple down...

    Jon P., December 2025
$1,500 - $4,500/nt
$2,000 - $5,000/nt
$2,500 - $9,500/nt
$3,200 - $8,000/nt
$6,000 - $15,000/nt
THE SHELDON JAMES WAY

Whether it’s choosing the perfect villa in Hawaii for your group or building a custom menu of high-end activities and services, we don’t leave any details to chance. Along with its trusted on-island partners, Sheldon James has got you covered from start to finish and can’t wait to show you how luxury villa travel really can be.

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.