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 45 luxury villa rentals

$1,100 - $6,000/nt
Hale Pua, Hawaii, Big Island
16 Guests • 5 Bedrooms • 6 Bathrooms
$1,200 - $3,800/nt
Dolphin Manor, Hawaii, Big Island
18 Guests • 5 Bedrooms • 6 Bathrooms
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Villa Reviews

  • 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

  • Claudine, France

    The apartment in Paris was wonderful, comfortable and in a part of Paris that made for a very walkable and enjoyable experience. The staff at Sheldon James made planning for our Paris trip very effective and easy, so we...

    Jenny M, May 2024

  • Villa Las Rocas, Los Cabos

    We’ve been using Sheldon James for all of our villa rentals and this was yet another perfect experience! The team really knows what they’re doing and always find the perfect villa for our events.

    Norm L, June 2023

  • Aqua Dream, St. Martin

    The staff were Excellent,very knowledgeable and professional.My Experience was Excellent looking forward doing business again.

    Vernon M, March 2024
$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
$1,500 - $2,500/nt
Kohala Sunsets, Hawaii, Big Island
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. 

5 star Review! ⭐️⭐️⭐️⭐️⭐️
$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
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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