10 Best Destinations for Hawaii Vacation Homes

For postcard views and amazing Hawaii vacation homes, head to the island"s windy western shore lined with resorts, condos and townhouses along attractive beaches with a backdrop of the West Maui Mountains. Renting one of the thousands of rental units in Lahaina, Kaanapali, Napili-Honokowai and Kapalua can be a way to stay on the beach and have a kitchen to keep dining costs down. Look for units a few floors up for better ocean views and the chance to see a humpback whale surface and spout. This area"s the Maui hub for whale-watching cruises and considered one of the best places in the world to see these giant, gentle creatures.

Don"t miss taking the kids to Kaanapali Beach, known for its beauty and spectacular sunsets with the islands of Lanai and Molokai in the distance. Adding to the allure: a daily cliff-diving ceremony off the beach"s northernmost cliffs.

More than 2,000 rentals also can be found along the South Maui stretch from Kihei to Makena. It"s considered the sunniest and driest part of the island—more Arizona than humid tropics. It"s generally less swank and more affordable than West Maui, especially in the 7-mile stretch of condos near Kihei. It"s a convenient place for snorkeling—especially if taking a tour to Molokini, a small island off the coast. It"s about an hour"s drive to reach Haleakalá National Park.

For more unique home rentals, the bohemian coastal towns of Paia and Haiku-Pauwela have a few hundred rentals, with a scattering of those near Makawao in Maui"s “Upcountry.” While they"re not on a beach, inland Upcountry communities show rich character and can even have distant views of the ocean. Each new elevation—especially on the climb up toward Haleakala National Park"s volcanic world—delivers a completely different landscape, from lush, green pastures and red dirt to sparse, foggy and otherworldly. Each can fuel young imaginations.

You can find close to 800 rentals (mostly condos) along Kauai"s south shore, a dry, sunny area anchored by Poipu and its much-lauded Poipu Beach Park, one of Kauai"s top beaches. Don"t miss the nearby “spouting horn,” a blow hole that fills with incoming waves and shoots water 20 feet or more into the air. There"s a wading pool at the park for toddlers and young swimmers, snorkeling off the beach and a chance to see sunbathing monk seals, green sea turtles and humpback whales spouting in the ocean. You can sneak in history lessons along the Koloa Heritage Trail.

If you want to be closer to Kauai"s North Shore with its lush, tropical beauty, look for places along the Coconut Coast north of Lihue. This is where most of the shopping and dining is concentrated before hitting the Princeville area. It"s also where some of the more affordable rentals can be. If you"re inland, don"t be surprised to be woken up by one of Kauai"s quirks: the crow of roosters that run wild with feral chickens throughout the island.

The elegantly developed area of Princeville rolls together stunning golf courses and high cliffs overlooking the ocean. You can hike down to a few coves, but the best bet for families is going to the 2-mile crescent beach at Hanalei Bay. This area, with its lush greenery and “sun showers” (rain while the sun is shining), also is the gateway to the dramatic Na Pali Coast, which any kid who"s a fan of “Jurassic Park” movies will likely recognize. Rentals include condos and many luxury homes that are more affordable if you choose one inland from the coast or can share lodging with other family members or friends.

You"ll find close to 2,000 rentals along the sunny western coast of Hawaii"s Big Island, the largest and youngest of the Hawaiian Islands. The 60-mile coast can be rocky, but you"ll find a white-sand beach, plentiful historic places and shopping, plus calm waters for snorkeling, especially among manta rays. You can find more than 1,000 additional rentals north of the Kona Coast, along the Kohala Coast.

If the chance to see an active volcano led you to pick to the Big Island, plan to spend at least a night or more in Hilo to minimize driving time and maximize time exploring Hawaii Volcanoes National Park. There are at least 600 rentals in the area, many of them affordable homes on the ocean, inland ponds or near tidepools. This is the wetter side of the island, so it"s also good for seeing waterfalls and botanical gardens and to learn about the night sky at Imiloa Astronomy Center.

If you want to experience Oahu like a local, skip Honolulu"s Waikiki Beach and head east about 20 miles across the Koolau Mountains on the Pali Highway to the island"s windward side. (Don"t miss the Nuuanu Pali Lookout for incredible views and hat-launching winds.) The thriving community of Kailua boasts some of the world"s most beautiful and lauded beaches with close to 600 cottages and beach houses to rent. It"s only a 20-minute drive south to Sea Life Park and Makapu"u Beach for watching body surfing, but chances are Kailua Beach Park and Kailua Bay, with windsurfing, kayaking and swimming, will be hard to leave. Bonus: There"s a great farmer"s market with tropical fruits and affordable family-friendly restaurants selling the island"s famous “plate lunches."

If you have teens aching to see world-class surfing, you"ll find a few hundred rentals along Oahu"s famed North Shore with its wow-inducing waves. Some of these rentals are condos—especially near Kaweia Bay—but most are one-of-kind beachfront or inland homes. Rentals also can be found clustered in Laie, home of the Polynesian Cultural Center; Kahuku; and Púpúkea near the Banzai Pipeline and Waimea Bay Beach Park and Waimea Valley.