Luxury villas in Maui

USA and Canada

Luxury Villas on Maui, Hawaii

47 properties

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Hawaii's Valley Isle, from Wailea sunshine to Kapalua greens

Maui pairs golden resort coastlines with volcanic peaks, waterfalls and some of Hawaii's best beaches. A private villa places you on the sunny leeward side around Wailea and Kapalua, with ocean-view pools, championship golf and easy reach of whale-rich waters, the Road to Hana and the heights of Haleakala.

Updated October 2026

  • Sunny leeward resort coasts at Wailea in the south and Kapalua in the west
  • Superb beaches and winter humpback whale watching in the channel
  • Championship golf, snorkelling at Molokini and world-class spas
  • The Road to Hana and sunrise from the summit of Haleakala
  • Ocean-view villas with private pools and concierge service
Known forWailea and Kapalua resorts, golden beaches, whale watching, Haleakala and the Road to Hana
Best time to visitApril to October for the driest weather; December to April for whale watching
Nearest airportKahului (OGG), central to the resort coasts
Ideal forFamilies, couples and groups wanting a sunny, resort-side island base

Villas in Maui

Wailea-MakenaWaileaKihei
47homes available
1–4bedrooms
up to 10guests

What's on in Maui

  1. December to April

    Humpback whale season

    Thousands of humpback whales gather in the warm channel between Maui and neighbouring islands, making winter the peak time for boat-based and shoreline whale watching.

  2. February

    Maui Whale Festival

    A month of community events in Kihei celebrating the humpbacks, centred on World Whale Day with a parade, live music and family activities.

  3. June

    Kapalua Wine and Food Festival

    One of Hawaii's longest-running culinary events, pairing celebrated chefs and winemakers for tastings and dinners on the Kapalua resort coast.

  4. Summer

    Maui Film Festival at Wailea

    An open-air film festival under the stars in Wailea, mixing premieres and celebrity tributes with the island's relaxed resort setting.

Maui through the seasons

  1. Winter (December – April)

    Humpback whale season

    Thousands of humpbacks fill the channels off Maui's leeward coast, often visible from villa lanais in Wailea and Kaanapali. Peak season, so secure homes and boat charters early.

  2. Spring (April – May)

    Calm seas and thinner crowds

    Snorkelling at Molokini and Honolua is at its clearest and the Road to Hana feels unhurried. A lovely window between whale season and summer holidays.

  3. Summer (June – August)

    Family season and flat leeward water

    Long dry days, gentle swimming beaches and sunrise trips up Haleakala suit multi-generation groups. Ocean conditions on the south and west shores are at their calmest.

  4. Autumn (September – November)

    The locals' favourite months

    Warm water, quieter beaches and softer rates make autumn the insiders' pick. Ideal for couples and remote-working stays with a private pool.

All 47 villas in Maui

Every home in Maui that can be booked with Smiling House, as a plain list.

Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.

The Area and Where to Stay

Maui's luxury villas concentrate on the sunny, sheltered leeward coasts. Wailea, on the south shore, offers manicured resort beaches, golf and reliable sunshine, while Kapalua and the northwest deliver dramatic coastline, greens and quieter sands. The central valley and the cooler Upcountry slopes of Haleakala give a different, ranch-and-farm feel. Our collection focuses on ocean-view, private-pool residences around Wailea and Kapalua, each supported by an island concierge.

Things to Do

Snorkel or dive the crescent islet of Molokini, watch humpback whales in winter, and swim the calm leeward beaches. Golfers have championship courses at Wailea and Kapalua, and the spas here rank among Hawaii's best. Adventurous days bring the winding Road to Hana, with waterfalls and rainforest, and a pre-dawn drive to the summit of Haleakala for sunrise above the clouds. Your concierge can arrange boat trips, guides, tee times and private tours.

Food and Local Flavour

Maui is a leader in Hawaii's farm-to-table movement, drawing on Upcountry farms, ranches and the surrounding ocean. Expect just-caught fish, island-grown produce, tropical fruit and Maui-grown coffee, alongside refined resort dining and relaxed local kitchens and food trucks. A private chef is an easy way to enjoy island ingredients by your villa's pool, and the concierge can secure sought-after reservations along the coast.

When to Visit

The leeward resort coasts stay warm and sunny year-round. April to October brings the driest, most settled weather, ideal for beaches, snorkelling and golf. Winter, roughly December to April, is a little wetter but greener and is prime humpback whale season in the channel. Evenings are cool at altitude, so pack layers for Haleakala; a private villa offers a calm, sun-filled base in any season.

Getting There

Most visitors fly into Kahului Airport (OGG), central to the island, with direct routes from the US mainland and connections via Honolulu. A hire car is essential for exploring the coasts, Upcountry and the Road to Hana, and the concierge can arrange private transfers, guides and inter-island flights. Basing yourself on the leeward coast keeps beaches, golf and dining close.

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