Hawaii

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 48 luxury villa rentals

$570 - $1,676/nt
$1,100 - $6,000/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
  • Ellice del Mar, California

    Alba was amazing to work with. Very professional, timely and enthusiastic! The home, while beautiful, was undoubtedly high maintenance and finicky. The smart features often weren’t working properly and required lots of contact with the property manager.

    Ken L, December 2024
  • Kishti East, Anguilla

    Our week in Anguilla was perfect. The villa was exactly as described. The location, the staff — magnificent. The food blew us away. (Dinner out was more of an activity though we should’ve taken advantage of the villa chef more.)...

    Emma J, December 2024
$1,200 - $3,800/nt
$1,200 - $1,500/nt
$1,260 - $5,000/nt
$1,300 - $4,500/nt
$1,440 - $3,300/nt
$1,500 - $4,500/nt

Tucked into the lush mountains of the Big Island, across historic and buzzy Oahu, to the golden sands of Maui and all scenic routes in between, Hawaii is a land of travel opportunity. We’re happy to recommend activities curated to your interests, like golfing one of its award-winning courses, surf lessons, or a traditional luau. 

$1,500 - $2,500/nt
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$1,575 - $2,200/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.