Hawaii Holidays

Luxury Hawaii holidays

Our luxury Hawaii holidays are less about doing and more about having the freedom to slow everything down. Wake up to Pacific views, take breakfast onto a shaded lanai and spend the afternoon moving between the beach and your own pool, with no timetable beyond sunset.

Across Maui, Oahu, Kauai and the Big Island, our Hawaii homes range from sleek coastal residences to secluded retreats surrounded by tropical gardens. Look for statement swimming pools, wide ocean-facing terraces, outdoor kitchens, hot tubs, fire pits and beautifully finished suites, with enough space for long dinners, late-night drinks and unhurried days at home.

Beyond your holiday retreat, charter a boat, play a round of golf beside the ocean, explore volcanic landscapes or discover a quiet stretch of sand away from the busiest resorts. The best luxury Hawaii holidays feel effortless: an extraordinary setting, a home worth staying in and every day shaped entirely around you.

Hawaii family holidays

Hawaii family holidays are made for relaxed beach days, outdoor adventures and plenty of time together. Families can swim in sheltered bays, snorkel among colorful marine life, visit waterfalls, explore volcanic landscapes and enjoy scenic drives with child-friendly stops along the way.

Our Hawaii homes with optional concierge make family travel seamless, with separate bedrooms, fitted kitchens, laundry facilities and spacious living areas featuring alongside add-on hotel-style services. Selected family-friendly rentals also feature private pools, games' rooms, private gyms, hot tubs, shaded lanais and barbecue areas, giving all ages plenty to enjoy during quieter days at home.

Oahu is a great choice for families wanting beaches, attractions and restaurants close by, while Maui, Kauai and the Big Island offer a slower pace and more nature-led experiences. Whether travelling with younger children, teenagers or several generations, Hawaii family holidays balance memorable days out with carefree home comfort.

Which Hawaiian island is best for your holiday?

Each Hawaiian island offers a different kind of escape, from lively beaches and city attractions to volcanic scenery and quieter coastal retreats.

Oahu holidays

Oahu suits travellers who want beaches, dining, shopping and famous sights within easy reach. Our Oahu vacation rentals and villas provide a comfortable setting for exploring Honolulu, Waikiki, the North Shore and the island’s historic landmarks.

Maui holidays

Maui is ideal for golden beaches, scenic drives, snorkeling and relaxed coastal days. Our Maui vacation rentals and villas range from ocean-view stays to spacious rentals with private pools, lanais and easy access to the island’s resorts and natural attractions.

Kaua'i holidays

Kaua'i is a strong choice for waterfalls, hiking trails, dramatic valleys and a quieter atmosphere. Our selection of Kaua'i vacation rental and luxury villas place you close to beaches and tropical scenery, with many offering pools, gardens and exotic outdoor living spaces.

Big Island holidays

The Big Island is best for volcanic landscapes, black-sand beaches, stargazing and varied outdoor adventures. Our Big Island vacation rentals offer plenty of space to unwind, with selected stays featuring private pools, ocean views and generous terraces.

FAQ's

Are Hawaii holidays suitable for families?

Yes! Many of the top things to do in Hawaii include great activities for multigenerational families. All ages will enjoy the sheltered beaches, snorkeling, wildlife encounters, waterfalls and accessible walking trails. Our Hawaii rentals are also equipped with useful amenities including fitted kitchens, laundry facilities, separate bedrooms and spacious living areas. Our luxury options meanwhile add private pools, games rooms and gyms into the mix.

Do Hawaii holiday homes have private pools?

Many Hawaii holiday homes feature private pools, with some also offering hot tubs, ocean-view terraces, barbecue areas and tropical gardens. Amenities vary between homes, so it's advisable to check the individual listing before booking. Alternatively contact our Sales team and they will find the perfect retreat for you!

Do I need a car during a Hawaii holiday?

A car hire offers added convenience when staying on Maui, Kauai and the Big Island. The beaches and attractions are spread across larger areas, so having the freedom to drive really helps. Visitors staying around Honolulu and Waikiki often manage without a car, although hiring a car for selected day trips can make exploring Oahu easier.

Which Hawaiian island is best for a first visit?

Oahu is often a convenient introduction to Hawaii because it combines beaches, cultural sights, restaurants and well-known attractions. Maui is another strong choice for first-time visitors seeking a slower coastal stay, with scenic drives and nature experiences to dive into.

Are Hawaii homes suitable for large families and groups?

Yes! Our collection of large Hawaii homes provide multiple bedroom suites, generous kitchens, spacious dining areas and outdoor entertaining spaces. Selected retreats also feature private pools, gyms, games rooms and large terraces overlooking the ocean, making them well suited to multigenerational holidays and special group celebrations.