Luxury Villa Rentals in Hawaii

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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 base from which to explore the island paradise.

Come with us and see how we deliver the aloha spirit with style.

View Region Guide

Discover our 24 luxury villa rentals

$2,750 - $4,500/nt

Puako Hylton, Hawaii, Big Island

10 Guests • 4 Bedrooms • 4 Bathrooms

$3,500 - $10,685/nt

Mauna Kea Resorts Bluffs 22, Hawaii, Big Island

10 Guests • 4 Bedrooms • 5 Bathrooms

$4,000 - $10,000/nt

Banyan House, Hawaii, Oahu

16 Guests • 8 Bedrooms • 9 Bathrooms

$6,000 - $9,500/nt

Hawaiiana Hale, Hawaii, Maui

10 Guests • 5 Bedrooms • 5 Bathrooms

$10,000 - $20,000/nt

Escape to Tranquility, Hawaii, Maui

26 Guests • 11 Bedrooms • 10 Bathrooms

Villa Reviews

Hokulani 825, Hawaii

Great place and amazing service. Very profession team we loved them and our get away there in Maui 🙂

Jamie E., May 2025
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
Point View Place, Colorado

Our Family recently stayed at Point View Place in Breckenridge, Colorado. Starting with our initial contact at Sheldon James (James D’Silva) the trip could not have been more Perfect! We have partnered with James D’Silva on a number of properties...

Barbara G., August 2022
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
We spent a great 10 days at Hacienda B5 in Punta Cana. We choose a villa experience to avoid the crowds of an all inclusive and we were not disappointed. The villa was perfect for our extended family of...

David P, March 2024
Wind Chime Villa, Turks and Caicos

Excellent trip as always! We love working with Sheldon James, they are always there when you need them and making the process so easy. Our family of 5 has been working with the company for years and have always...

Julie B, December 2024
The One, Punta Mita

The home is gorgeous with incredible attention to detail with all the amenities it was like your own private boutique hotel . The staff is absolutely a major highlight of this experience. They are at your every beck and call...

Julie B., January 2026
Hacienda Magica, Riviera Maya

We had visited this villa many years ago so knew the basic set up. The new owners have kept the charm and updated it to be more comfortable and modern. It is spacious, with multiple places both for groups to...

Leslie H., March 2026

$570 - $1,676/nt

Hokulani 825, Hawaii, Maui

10 Guests • 3 Bedrooms • 3 Bathrooms

$1,440 - $3,300/nt

Kailua Beach Villa, Hawaii, Oahu

12 Guests • 5 Bedrooms • 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 for you, like golfing one of its award-winning courses, surf lessons, or a traditional luau.

$1,950 - $2,500/nt

Diamond Head Grandeur, Hawaii, Oahu

10 Guests • 5 Bedrooms • 5 Bathrooms

$2,000 - $5,000/nt

Hale Pakika at Kukui’ula, Hawaii, Kauai

12 Guests • 5 Bedrooms • 5 Bathrooms

$2,000 - $5,000/nt

Kipuka Lani, Hawaii, Big Island

8 Guests • 4 Bedrooms • 4 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.

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Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL:

Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL:

Discover our 24 luxury villa rentals in Hawaii

THE SHELDON JAMES WAY

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