Luxury villas in Hawaii

USA and Canada

Luxury Villas in Hawaii

103 properties

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Volcanic islands, gold-sand beaches and the ease of aloha

Hawaii is a chain of volcanic islands in the mid-Pacific, each with its own character: Oahu's surf towns and city energy, Maui's resort coasts, the Big Island's lava landscapes and Kauai's green cliffs. Renting a luxury villa here trades hotel corridors for private pools, ocean-view lanais and concierge support, with space for families and groups to settle into island time.

Updated October 2026

  • Maui's Kaanapali and Kihei coasts, with calm swimming beaches and channel views to Lanai
  • Oahu's North Shore around Haleiwa, home of winter's legendary surf breaks
  • Kailua-Kona and the Kohala Coast on the Big Island, gateway to volcano country
  • Humpback whale season from December to March, at its best off Maui
  • Private-pool villas with lanais, ocean views and dedicated island concierge service
Known forWorld-class beaches and surf, volcanoes, whale watching, Polynesian culture and resort coasts on Maui, Oahu and the Big Island
Best time to visitApril to October for the driest weather; December to March for humpback whales and big North Shore surf
Nearest airportHonolulu (HNL) for Oahu, Kahului (OGG) for Maui, Kona (KOA) for the Big Island
Ideal forFamilies, surfers, honeymooners and multi-generational groups who want ocean-view space and privacy

Villas in Hawaii

Wailea-MakenaPuakoKailua Kona
103homes available
1–15bedrooms
up to 48guests
7with a pool
3book instantly →

Where to stay in Hawaii

Maui47Big Island35Kauai4Oahu3

What's on in Hawaii

  1. November

    Kona Coffee Cultural Festival

    Held in and around Kailua-Kona on the Big Island, this long-running festival celebrates the harvest of the famous Kona coffee belt with farm tours, tastings and community events.

  2. Mid-November to December

    Vans Triple Crown of Surfing

    The world's best surfers converge on Oahu's North Shore near Haleiwa when winter swells arrive. Watching from the beach at the famous breaks is one of sport's great free spectacles.

  3. April, the week after Easter

    Merrie Monarch Festival

    Hawaii's most prestigious hula festival, held in Hilo on the Big Island, gathers the finest halau for a week of competition and craft fairs. Tickets are scarce, but the festival atmosphere spreads across the island.

  4. 1 May

    Lei Day

    May Day is Lei Day in Hawaii, marked with lei-making contests, hula and music across the islands, most visibly in Honolulu's parks. A gentle, fragrant introduction to island tradition.

  5. September

    Aloha Festivals

    A statewide celebration of Hawaiian music, dance and history centred on Oahu, with a floral parade through Waikiki and free cultural events. The largest showcase of Hawaiian culture in the islands.

Hawaii through the seasons

  1. Winter (December – March)

    Whales and giant surf

    Humpback whales fill the channels off Maui while huge swells light up Oahu's North Shore. The leeward villa coasts stay warm and swimmable throughout.

  2. Spring (April – May)

    Quiet beaches and hula season

    Settled weather returns, crowds thin after Easter and the Merrie Monarch Festival brings hula's finest to Hilo. A superb-value window for villa stays.

  3. Summer (June – August)

    Calm seas and family time

    The driest, calmest ocean conditions of the year, ideal for snorkelling, sailing and long beach days. Peak family season, so villas book early.

  4. Autumn (September – November)

    Harvests and shoulder-season ease

    Warm seas, thin crowds and the Kona coffee harvest on the Big Island. Aloha Festivals fill Oahu with music and parades in September.

All 103 villas in Hawaii

Every home in Hawaii 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

Each island offers a different holiday. On Maui, the Kaanapali resort coast and the beach town of Kihei anchor the sunny leeward side, with calm swimming bays, golf and sunset views across the channel to Lanai and Molokai. Oahu pairs Honolulu and Waikiki with the country pace of the North Shore, where Haleiwa's surf-town charm sits beside famous winter breaks. The Big Island splits between the sunny Kona and Kohala coasts, where most villas cluster around Kailua-Kona, and the lush volcano country of the east. Kauai, the garden isle, suits travellers drawn to cliffs, canyons and quiet beaches. Our collection concentrates on these leeward coasts: private-pool residences and ocean-view estates where the weather is most reliable and beaches, dining and golf are close at hand.

Things to Do

Hawaii rewards both energy and idleness. Snorkel the reefs of Maui's south shore or the clear Kona Coast, learn to surf in the gentle rollers off Waikiki or Kihei, and in winter watch the world's best ride giants on Oahu's North Shore near Haleiwa. On the Big Island, Hawaii Volcanoes National Park reveals craters and lava fields, while Mauna Kea's summit offers some of the clearest stargazing on Earth. Maui adds the sunrise spectacle of Haleakala and the waterfall-laced Road to Hana. Between adventures there is whale watching from December to March, championship golf on the resort coasts and long afternoons on gold-sand beaches. Your concierge can arrange boat charters, helicopter flights, guides and private luau experiences.

Food and Local Flavour

Hawaiian food culture layers Polynesian roots with Japanese, Filipino, Portuguese and mainland influences. Expect just-landed ahi and mahimahi, poke bowls from local counters, plate lunches, tropical fruit and shave ice on hot afternoons. The Big Island grows the celebrated Kona coffee on the slopes above Kailua-Kona, while Maui's upcountry farms supply the islands' best restaurants. Resort coasts hold refined oceanfront dining rooms, and towns such as Haleiwa and Kihei add food trucks, fish markets and easy-going local kitchens. A private chef is the most relaxed way to enjoy island produce at your villa, and the concierge can secure sought-after tables and organise a traditional luau.

When to Visit

The leeward coasts where most villas sit stay warm and swimmable all year, so timing is about emphasis rather than avoiding a bad season. April to October brings the driest, most settled weather, ideal for snorkelling, sailing and beach days. December to March is greener and slightly wetter, with humpback whales filling the channels off Maui and enormous winter surf hitting Oahu's North Shore. The holiday weeks and mid-summer are the busiest periods, so book villas well ahead. Shoulder months, especially May, September and October, combine fine weather with quieter beaches and easier restaurant reservations, making them a favourite window for villa travellers.

Getting There

Honolulu International (HNL) on Oahu is the state's main gateway, with direct flights from North America, Asia and the Pacific. Maui's Kahului Airport (OGG) and Kona International (KOA) on the Big Island also receive direct mainland services, so most villa guests fly straight to their island. Short inter-island flights link the chain in around thirty to forty minutes. A hire car is essential on every island, as beaches, trailheads and towns are spread along long coastal roads. The concierge can arrange private transfers, inter-island connections and car delivery so arrival is seamless.

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