Luxury Villa Rentals in Oahu

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Whether beachfront or tucked back a bit into the hillside, our luxury villas in Oahu are classically Hawaiian, with unfussy tropical style and plenty of spaces that blur the line between indoor and outdoor.

Whether beachfront or tucked back into the hillside, our luxury villas in Oahu are quintessentially Hawaiian.

Discover our 10 luxury villa rentals

$4,000 - $10,000/nt

Banyan House, Hawaii, Oahu

16 Guests • 8 Bedrooms • 9 Bathrooms

$1,440 - $3,300/nt

Kailua Beach Villa, Hawaii, Oahu

12 Guests • 5 Bedrooms • 5 Bathrooms

$1,950 - $2,500/nt

Diamond Head Grandeur, Hawaii, Oahu

10 Guests • 5 Bedrooms • 5 Bathrooms

$2,500 - $4,500/nt

Kailua King Estate, Hawaii, Oahu

18 Guests • 8 Bedrooms • 9 Bathrooms

$2,500 - $4,200/nt

Lanikai Hillside Estate, Hawaii, Oahu

10 Guests • 5 Bedrooms • 6 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
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
Indigo (formerly Greatview), Jamaica

Sheldon James was truly i n c r e d i b l e to work with. James and Alba planned a very special family reunion trip to Jamaica and took...

Sophie G, March 2026
West Enclave 8, Los Cabos

Our friends & family had a magnificent time at the villa. The staff was superb, the decoration was right on point, the beds were comfortable, the cooking was delicious, and the whole experience was entertaining and relaxing.

Mark C, December 2023
Sugar Kube, Turks and Caicos

It was an amazing Villa loved every moment of our honeymoon. The staff were amazing they provided such a great service from Housekeeping to our 2 masseuse Melanie and Marie and your chefs Juan and Emara, Great food. We will...

Luis R, December 2024
Villa Bash, Turks and Caicos

WOW, WOW,WOW. This was our first trip through Sheldon James. Unfortunately no outer vacation will ever live up to what we experienced. We rented Villa Bash in Turks and Caicos for my wife’s 50th birthday with 5 other couples. We...

Alex D., December 2025
Casa Minitas, Dominican Republic

Great working with Alba who was attentive and prompt for each follow up.

Marco, February 2026

$2,850 - $8,800/nt

Kahala Beachside Estate, Hawaii, Oahu

14 Guests • 7 Bedrooms • 8 Bathrooms

$4,000 - $12,000/nt

Hale Wilikoki, Hawaii, Oahu

12 Guests • 6 Bedrooms • 6 Bathrooms

As Hawaii’s “busiest” island (it’s all relative), Oahu offers perhaps the most varied activities in the state. Think historic temples, famous hikes, and food tours blending tastes from around the world. But don’t worry — the quiet is easy to find, and all it takes is one sunset to convince you to slow down.

$4,000 - $11,000/nt

Portlock Estate, Hawaii, Oahu

12 Guests • 6 Bedrooms • 7 Bathrooms

$4,700 - $9,000/nt

Kailua Kai Estate, Hawaii, Oahu

18 Guests • 9 Bedrooms • 7 Bathrooms

Rates upon request

Kailua Beachside, Hawaii, Oahu

10 Guests • 5 Bedrooms • 5 Bathrooms

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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 10 luxury villa rentals in Oahu

THE SHELDON JAMES WAY

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