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
Hokulani 825, Hawaii, Maui
10 Guests • 3 Bedrooms • 3 Bathrooms
$1,100 - $6,000/nt
Hale Pua, Hawaii, Big Island
16 Guests • 5 Bedrooms • 6 Bathrooms
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Villa Reviews

  • Makena Kai, Hawaii

    Our family has worked with James D’Silva for several years to create perfect villa vacations that perfectly meet our needs. We have booked vacations with him in Hawaii, Cabo San Lucas, Jamaica, etc. He and his team are always customer...

    Brian M, July 2021

  • 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

  • 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
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$1,200 - $3,800/nt
Dolphin Manor, Hawaii, Big Island
18 Guests • 5 Bedrooms • 6 Bathrooms
$1,200 - $1,500/nt
Maui Ocean Breeze, Hawaii, Maui
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,260 - $5,000/nt
Hale Mahina Hou, Hawaii, Kauai
12 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,300 - $4,500/nt
Hale Pomaika’i Mau, Hawaii, Kauai
10 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,440 - $3,300/nt
Kailua Beach Villa, Hawaii, Oahu
12 Guests • 5 Bedrooms • 5 Bathrooms
$1,500 - $4,500/nt
Honu Awa, Hawaii, Kauai
8 Guests • 4 Bedrooms • 4.5 Bathrooms

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
Kohala Sunsets, Hawaii, Big Island
8 Guests • 4 Bedrooms • 4.5 Bathrooms
5 star Review! ⭐️⭐️⭐️⭐️⭐️
$1,575 - $2,200/nt
Rainbow Hale, Hawaii, Maui
8 Guests • 4 Bedrooms • 3.5 Bathrooms
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.

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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