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.
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 40 luxury villa rentals in Hawaii
Discover our 40 luxury villa rentals
$1,200 - $1,500/nt
Maui Ocean Breeze, Maui, Hawaii
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,260 - $5,000/nt
Hale Mahina Hou, Kauai, Hawaii
12 Guests • 4 Bedrooms • 4.5 Bathrooms
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$1,300 - $4,500/nt
Hale Pomaika’i Mau, Kauai, Hawaii
10 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,440 - $3,300/nt
Kailua Beach Villa, Oahu, Hawaii
12 Guests • 5 Bedrooms • 5 Bathrooms
$1,500 - $2,500/nt
Kohala Sunsets, Big Island, Hawaii
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,500 - $4,500/nt
Honu Awa, Kauai, Hawaii
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,575 - $2,200/nt
Rainbow Hale, Maui, Hawaii
8 Guests • 4 Bedrooms • 3.5 Bathrooms
$1,600 - $2,800/nt
Makena Aloha, Maui, Hawaii
10 Guests • 6 Bedrooms • 4.5 Bathrooms
$1,950 - $2,500/nt
Diamond Head Grandeur, Oahu, Hawaii
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$2,000 - $5,000/nt
Kipuka Lani, Big Island, Hawaii
8 Guests • 4 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.
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.
