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Top Hawaiian Homes for Groups and Executive Retreats

It’s that time of year again–the big office retreat, which means days of team-building activities, problem solving puzzles, and discussions on improvement. Executive retreats can also mean socializing and fun at night, or exploring your destination’s best attractions. Perhaps you are just looking for a great large home for a family vacation, a place that has bedrooms for everyone so no one has to sleep on the couches and floor. No matter the reason for the trip, Hawaii has several large vacation homes and condos available for large groups, and some of them are too spectacular to pass up. The homes listed below have it all–sleeping quarters for 12+ people, spacious kitchens, beautiful sitting rooms, and incredible ocean views. And while on your trip, relax and let us help you with group activities such as snorkeling, scuba diving, kayaking, fishing, and so much more! Browse our selections below to find the perfect home this vacation season for your group.

Heaven Hales, The Big Island

The beautiful Heaven Hales homes is one of the Big Island's finest vacation rental packages. This two house estate is located in a prestigious neighborhood with privacy and perfect views of sunsets and the ocean. The Heaven Hales sleeps 21 people comfortably, comes with full amenities such as internet, TVs, DVD players, and a private hot tub and pool, and has a gourmet kitchen perfect for dinner parties and group meals. This location is just minutes from everything in Kona such as the airport, shopping, beaches, and great dining options. Visitors will love the large pool complete with a swim-up wet bar and an attached sandy bottom wade pool. Everything about this home speaks luxury and relaxation for large groups of people.

Beds: 18
Baths: 9
Sleeps: 21


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Tiki Moon Villas, Oahu

The Tiki Moon Villas are a group of 5 separate bungalows on the North Shore of Oahu, taking up a half acre of property. If your group is looking for beautiful beachfront views, these villas could be right for you. Not only is the view amazing, but these villas are located in close proximity to several activities on the island: 1 minute walk to Polynesian Cultural Center, 30 minute drive to the surf community of Hale’iwa, 20 minute drive to Waimea Valley, 15 minute drive to Turtle Bay resort for golfing, or just a walk out the back door to play on the beach. These villas come with 8 bedrooms and 6 full bathrooms, sleeping approximately 25 guests. Ammenitites include beach umbrellas, chairs, and an on-site grill so your group can enjoy a great Hawaiian cookout.

Beds: 8
Baths: 6
Sleeps: 25


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Aloha Villas, Maui

The Aloha Villas are a collection of 4 separate beachfront villas, located in South Maui. With 12 bedrooms and 12 full bathrooms, the Aloha Villas can sleep 24 guests comfortably and includes housekeeping services. The private pool and hot tub are sure to be a hit with the kids, or even the adults for a nighttime swim. Guests can walk out the back door to enjoy time on the beach, or drive 5 minutes for some of the best snorkeling and scuba diving Maui has to offer.

Beds: 12
Baths: 12
Sleeps: 24


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Swaying Palms, Kauai

This grand Kauai-based home encompasses a true Hawaiian vacation from the rich decor to the stunning ocean views. Located in Haena, the Swaying Palms is a secluded home, making it ideal for large group gatherings or executive retreats. The home comes with internet access, HD TV, cable, private laundry facilities, a BBQ grill, and a large gourmet kitchen. Relax in paradise and discover what truly serene solitude really is.

Beds: 7
Baths: 5
Sleeps: 14


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Lahaina Oceanfront Estates-Ali'i Hale and Princess Hale

Separated into two separate homes, the Alii and Princess Hale homes are the perfect place to relax and listen to the sounds of waves crashing in and palm trees swaying. Watch whales breaching during the winter season and glowing sunsets from the privacy of your own backyard pool and Jacuzzi tub. Enjoy spacious bedrooms, oceanfront views, a formal dining room, and a gourmet kitchen. The Alii and Princess Hale are also located just minutes from downtown Lahaina where guests will enjoy shopping, great nightlight, and access to incredible Hawaiian cuisine.

Beds: 12
Baths: 6
Sleeps: 16


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Hale Napili, Maui

The Hale Napili is the perfect tropical escape, located on Maui's Western shores in the stunning Napili area. Take in the incredible ocean views from your own private backyard, including dramatic views of the Molokai Island. The home is surrounded by brilliant foliage and fragrant flowers, ensuring absolute privacy from other homes in the area. The Hale Napili resides in a private community, protected by a gate, and includes access to a luxurious pool and outdoor hot tub just 2 minutes from the residence. A private beach is also available minutes from the home, where you can kayak, whale watch, or watch green sea turtles. Public beaches, restaurants, golf courses, shopping, and other activities are all located within a 5 minute drive from the home.

Beds: 8
Baths: 4
Sleeps: 14


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