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 25 luxury villa rentals

$1,200 - $1,500/nt
Maui Ocean Breeze, Hawaii, Maui
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,500 - $2,500/nt
Kohala Sunsets, Hawaii, Big Island
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,575 - $2,200/nt
Rainbow Hale, Hawaii, Maui
8 Guests • 4 Bedrooms • 3.5 Bathrooms
$1,600 - $2,800/nt
Makena Aloha, Hawaii, Maui
10 Guests • 6 Bedrooms • 4.5 Bathrooms
$2,000 - $5,000/nt
Kipuka Lani, Hawaii, Big Island
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$2,200 - $4,000/nt
Garuda Estate, Hawaii, Maui
6 Guests • 3 Bedrooms • 3 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. 

$2,200 - $4,500/nt
Blue Wave, Hawaii, Big Island
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$2,250 - $4,250/nt
Sea Diamond Estate, Hawaii, Maui
10 Guests • 5 Bedrooms • 6 Bathrooms
$2,450 - $4,500/nt
Hale Kolea Kai, Hawaii, Big Island
12 Guests • 5 Bedrooms • 4.5 Bathrooms
$2,750 - $4,500/nt
Puako Hylton, Hawaii, Big Island
10 Guests • 4 Bedrooms • 4 Bathrooms
$2,850 - $5,000/nt
Paradise Cove, Hawaii, Maui
6 Guests • 3 Bedrooms • 3.5 Bathrooms
$3,000 - $6,000/nt
Pacific View, Hawaii, Maui
12 Guests • 6 Bedrooms • 4.5 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 focus Hand-select villas A 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.

Internal Info

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

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