Villa Plantation Paradise Point - Image 1
Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island’s development. The sweet fruit were grown out of large plantation estates, which serve as the inspiration for Plantation at Paradise Point whose lavish architecture is inspired in part by those same historical sites. Situated on Oahu’s windward shore, near Kailua Beach and Paradise Point, groups of travelers no large...

Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island’s development. The sweet fruit were grown out of large plantation estates, which serve as the inspiration for Plantation at Paradise Point whose lavish architecture is inspired in part by those same historical sites. Situated on Oahu’s windward shore, near Kailua Beach and Paradise Point, groups of travelers no larger than ten can set up their dream vacation on its luxury grounds and in the five stately guest suites for what will no doubt become a memorable trip.

Plantation at Paradise Point offers both supreme security and privacy. The courtyard has a seductive lagoon-style swimming pool featuring cascading waterfalls next to a comprehensive cabana and an irresistible island spa. The home has two well-furnished lanais with tiki torches and alfresco dining from which to enjoy dazzling oceanfront views or the delightful tropical garden. This home is also totally wheelchair accessible, features total home entertainment systems and provides guests staying here with snorkeling equipment.

The home has a stunning and highly refined sense of decor. Artisanal etched windows, stained glass, natural stone tiling and African mahogany carvings are only a few of the unique aspects found. The kitchen has no shortage of anything with only the best appliances, glistening granite countertops and table surfaces perfect for chatting with the cook or snacking on their creations.

Guests suites offer a variety of bedding options, ranging from king, queen or twin size beds in large plush rooms with a gorgeous sense of style. Each room features an en-suite bathroom and the choice of air conditioning or ceiling fans. Additionally, the master suite’s bathroom has a Jacuzzi, while other rooms have their own private lanais.

Plantation at Paradise Point is also known as the ‘Obama Winter White House’ since it is a getaway favorite of the US President and his family when escaping the cold. Kailua might not be Honolulu, but there are no shortage of amazing experiences and activities. Pristine beaches, kayaking or snorkeling are what makes this part of the island so coveted. Aside from the natural features of the region, there are also delicious gourmet restaurants, elite country clubs with championship golf courses and plenty of shopping. Aloha!

Interior features

  • Wheel chair accessible
  • Central air conditioning
  • Heating system
  • Ceiling fans
  • Hairdryer
  • Toiletries
  • Electric safe
  • Media room
  • Cable TV
  • DVD Player
  • Blu-Ray player
  • CD player
  • iPod docking station
  • Home Theatre
  • Wi-Fi access
  • Telephone
  • Printer
  • Washer/Dryer
  • Kitchen
  • Fitness Room

Outdoor features

  • Alarm system
  • Heated lagoon pool
  • Waterfall
  • Tiki torches
  • Heated Jacuzzi
  • Outdoor shower
  • Beach chairs
  • Beach towels
  • Snorkeling equipment
  • Flotation devices
  • Pool side lanai
  • Icemaker
  • Gas BBQ grill
  • Alfresco dining
  • Parking
  • Gated property
Daily manager availability
Concierge

Our Guest Experience Concierge is here to help you plan every detail of your stay. From restaurant reservations and yacht charters to private chefs and local experiences, we ensure your villa holiday is seamless and unforgettable.

1 minute drive to church and Pinky’s Grill Restaurant
2 minute drive to grocery store
3 minute drive to The Medical Corner clinic
5 minute drive to:
Kailua town
24 Hours Fitness center
Kailua District Park tennis court
Luana Hills C.C Golf Course
Castle Medical Hospital
25 minute drive to Honolulu Airport

This villa is perfect for families seeking space and privacy, couples celebrating special occasions, and groups of friends who appreciate luxury and exceptional service.

Villa Plantation Paradise Point

Oahu

KEY SPECIFICATIONS

5 Bedrooms
10 Guests
Swimming Pool

Starting from 4,500 $/night*

Discover the finest local restaurants, markets, and culinary experiences. Our concierge can arrange private wine tastings, cooking classes with local chefs, and reservations at the region's most acclaimed dining establishments.

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Private Chef & Multilingual Butler service are included

Villa Plantation Paradise Point

Oahu

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Starting from 4,500 $/night*

Guest experience

An absolutely magical experience! The villa exceeded all our expectations. The attention to detail, the stunning views, and the impeccable service made our vacation truly unforgettable. The private chef prepared the most amazing meals every evening.

Sarah & James, London

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Frequently asked questions

Many of our luxury villas in Villas include a dedicated private chef and butler service. Check individual villa listings for specific service details.

Villas offers wonderful experiences throughout the year. The peak season typically offers the best weather and most vibrant atmosphere, while shoulder seasons provide a more relaxed experience with fewer crowds. Contact our concierge team for personalized recommendations.

Simply browse our destinations, select a villa that suits your needs, and submit an enquiry. Our team will get back to you within 24 hours with availability and a detailed proposal.

Cancellation terms vary by villa and season. Our team will provide full details in your booking proposal before you confirm.

Absolutely. From private wine tastings to yacht excursions, we can arrange a wide range of curated experiences to make your stay unforgettable.