Island escapes to Maui, Molokai, and more

The Deal

Few places satisfy the urge for a carefree tropical vacation like the islands of Hawaii – what with its white-sand beaches, lush landscapes, pounding surf, and rich Polynesian culture. And while you can't really go wrong when it comes to travel to Hawaii, fall is the sweetest time to visit. During these few months, there are fewer crowds, lower resort rates and discounted packages, and powerful northern swells (in October) that make for primo surfing. We've rounded up five great deals to Kauai, Maui, and more, with prices from $139/night! 

Oahu Hotel and Breakfast Package from $139/Night
From the world-renowned surfing seaboard on its North Shore to the historic site of Pearl Harbor to the bustling stretch of Waikiki Beach, it’s no wonder that Oahu is Hawaii’s most visited island. Centrally located in downtown Honolulu, the Ala Moana Hotel offers spacious and affordable guestrooms just steps from world-class shopping and scenic Ala Moana Beach Park. The recently renovated property features a brand-new rooftop pool and sundeck and a state-of-the-art fitness center. Book the low-priced Breakfast Package to enjoy rates as low as $139/night. This deal is valid through December 21 and includes daily buffet breakfast for two.

Big Island Family Special from $294/Night
An unforgettable adventure awaits visitors on Hawaii’s Big Island, renowned for its diverse   landscape that includes snow-covered mountains, lush rainforests, black-sand beaches, and active volcanoes. Located on the island’s stunning western Kohala Coast, the 62-acre Hilton Waikoloa Village offers elegantly furnished guestrooms in a gorgeous oceanfront setting. The family-friendly resort also boasts a freshwater pool with dramatic waterfalls, a day camp for children ages 5 to12, and a Dolphin Quest Learning Lagoon where kids can interact and swim with the friendly ocean mammals. Available through December 31, the Ocean Explorer Family Escape covers a 4-night stay for two adults and two kids, including daily buffet breakfast and one glass-bottom boat cruise. Kids also receive a backpack filled with goodies, including an underwater camera, coloring books, ocean fish guides, and more. Rates start at just $294/night per room.

Kauai Romance Package from $700/Night
From the spectacular sea cliffs of the Napali Coast to the natural lava caves and lush jungles along the Wailua River, Kauai has some of the most dramatic scenery of all the Hawaiian Islands. Situated on world-renowned Poipu beach on the island’s southern shore, the Ko’a Kea Hotel and Resort has 121 luxury beachfront rooms with private lanais, a romantic oceanfront restaurant, and a top-rated spa. Couples looking for some romance should consider booking the resort’s Tropical Desire package. Available year round, the offer includes a 3-night stay in an ocean-view guestroom with breakfast daily, a 3-course dinner for two, a 1-hour couples massage, and a midsize car rental. Rates start from $700/night.

Molokai 3-Night Getaway with Airfare from $759
Anyone in search of unspoiled scenery should head straight to the tiny island of Molokai, renowned for its towering sea cliffs, ancient Polynesian fishponds, and 32 miles of natural barrier reef. Located on picturesque Kamilolao Beach, the Aqua Hotel Molokai has a full-service spa featuring traditional Lomi Lomi massage treatments, an onsite restaurant serving tasty island cuisine, and 53 oceanfront bungalows equipped with kitchens and private lanais. Activities abound on this island, from guided whale-watching excursions from Kaunakakai Harbor and nature hikes past thunderous waterfalls, rugged shorelines, and protected rainforests. This affordable package from Pleasant Holidays includes three nights’ accommodations and round-trip airfare from San Francisco. The offer is available through December 7 and costs just $759.

Maui 5-Night Villa Rental with $500 Resort Credit, from $895/Night
Maui has been dubbed the magic isle, and it’s easy to see why. Lush rainforests, gorgeous white-sand beaches, and spectacular volcanic craters lure millions of visitors each year to one of the world’s most enchantingly islands. For a lavish retreat on Maui’s stunning south side, consider the Five-for-Five special offer available at the Ho’olei at Grand Wailea. This luxury oceanfront resort is currently offering a $500 resort credit to guests who stay five consecutive nights from now through December 21. The credit is good for use at the resort’s dining and golf facilities, spa, and retail outlets. Guests also enjoy golf privileges and reduced green fees at five area golf courses; guided ocean activities and whale-watching trips can be arranged through the concierge. Rates start at $895/night for a deluxe 3-bedroom villa with garden views.

The Dollars

Taxes and fees are additional.

The Catch

Saying aloha in Hawaiian also means saying goodbye.

Booking Details

For the Oahu deal, visit www.outrigger.com or call 1-866-956-4262.

For the Big Island special, visit www.hiltonwaikoloavillage.com or call 1-808-886-1234.

For the Kauai package, visit www.koakea.com or call 1-808-828-8888.

For the Molokai getaway, visit www.pleasantholidays.com or call 1-800-742-9244.

For the Maui villa offer, visit www.hooleiatgrandwailea.com or call 1-877-346-6594.