Maui4,113 rentals · avg $673/nt · ★ 4.84The 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
Kauai1,585 rentals · avg $761/nt · ★ 4.85The garden island: the North Shore's mountains and Hanalei Bay in summer, sunny Poipu in winter, and the Coconut Coast in between.PrincevilleHanaleiPoipuKapaaExplore Kauai
Oahu972 rentals · avg $629/nt · ★ 4.80City 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 Island1,656 rentals · avg $675/nt · ★ 4.86Volcanoes 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