Kailua
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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 6 luxury villa rentals

$1,440 - $3,300/nt
Kailua Beach Villa, Hawaii, Oahu
12 Guests • 5 Bedrooms • 5 Bathrooms
$2,500 - $4,500/nt
Kailua King Estate, Hawaii, Oahu
18 Guests • 8 Bedrooms • 9 Bathrooms
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$2,500 - $4,200/nt
Lanikai Hillside Estate, Hawaii, Oahu
10 Guests • 5 Bedrooms • 6 Bathrooms
$4,000 - $12,000/nt
Hale Wilikoki, Hawaii, Oahu
12 Guests • 6 Bedrooms • 6 Bathrooms
$4,700 - $9,000/nt
Kailua Kai Estate, Hawaii, Oahu
18 Guests • 9 Bedrooms • 7 Bathrooms
Villa Reviews

  • The Point Luxury Villa, Costa Rica

    Another fabulous vacation in a first-class villa in a spectacular location in Costa Rica. Excellent service from Sheldon James and all the onsite staff. Highly recommended.

    Anne P., February 2025

  • Round Rock Estate, Anguilla

    Neil O, December 2024

  • Villa Lorenne, Dominican Republic

    What a dream vacation!! The villa is beautiful. The staff was phenomenal. Our celebrations were so special. No one wanted to leave!!!

    Sima I, April 2025

  • Beach Enclave GB Oceanview Villa 6bdr, Turks and Caicos

    We had a great experience at beach enclave. 5 star property and service. The only confusion was at first when the villa number/size was slightly different than what we thought we signed up for, but nonetheless we had a...

    Matt P, February 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

  • Casa La Laguna, Los Cabos

    The house was stunning! Every person on the staff was wonderful and took such great care of us. Whatever we needed, they made sure they got…down to the beer pong we asked for! Would definitely vacation here again.

    Kyle L., January 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

  • Tremblant Village Walk, Quebec

    Wade and the Sheldon James team were incredibly helpful and provided a true 5-star service and product. Their chalet recommendation was a perfect fit for our needs and the attention to detail during our entire stay was impeccable including the...

    Bernard A, April 2025

  • Villa Embrace, St. Barts

    I have been working with James for over 10 years to locate beautiful homes for our special family vacations across the world. He has a gift of listening to his clients and is the most patient human being on this...

    Carol W., March 2024

  • Villa Aquazure, Turks and Caicos

    Great experience, great location, and great service by Axel. My family and I had the best vacation.

    Dragan N., November 2024
Rates upon request
Kailua Beachside, Hawaii, Oahu
10 Guests • 5 Bedrooms • 5 Bathrooms

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

Internal Info

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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:

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