Maui4,500 rentals · avg $651/nt · ★ 4.79The all-rounder: the most beaches, resorts and condos in Hawaii, from Kaanapali and Kapalua in the west to Kihei and Wailea in the south.KaanapaliKapaluaKiheiWaileaMaalaeaHanaExplore Maui
Kauai1,681 rentals · avg $744/nt · ★ 4.82The garden island: the North Shore's mountains and Hanalei Bay in summer, sunny Poipu in winter, and the Coconut Coast in between.PrincevilleHanaleiPoipuKapaaExplore Kauai
Oahu1,169 rentals · avg $594/nt · ★ 4.70City and beach: walk everywhere in Waikiki, or trade the bustle for Ko Olina's calm lagoons and Turtle Bay on the North Shore.WaikikiHonoluluKo OlinaTurtle BayExplore Oahu
Big Island1,769 rentals · avg $666/nt · ★ 4.82Volcanoes and sunshine: Kona's oceanfront condos at the best prices in Hawaii, and the Kohala Coast's white-sand resort beaches.KonaKohala CoastWaikoloaMauna LaniExplore Big Island