O‘ahu’s Windward Coast B&Bs and Resort Hotel

If you’re prepared for rain and wind, common weather conditions on this side of the island, camping is prevalent on the windward coast in the beach parks, as are vacation rentals in Kailua and Hawai‘i Kai. If you’re not ready to fend so much for yourself, a nice middle ground are Kailua’s array of bed-and-breakfast accommodations, a great way to escape the Waikiki scene to one of the prettiest white sand beaches on the island, or for a more luxurious stay, the sole resort in the region is the high-class Kahala Hotel & Resort.

Southeast O‘ahu

At the end of Kahala Avenue in the affluent Kahala neighborhood is the luxurious Kahala Hotel & Resort (5000 Kahala Ave., 808/739-8888, $495-675). The rooms and suites are decorated in a light tropical palette with island accents, and guests can enjoy the secluded white sand beach just steps away. The hotel has its own private lagoon where guests can interact with dolphins and other sea creatures. A swimming pool, high-end spa with 10 private treatment suites, and a beachfront fitness center are a few of the amenities.

The Ko‘olau Mountains in Kailua.
Find the right place to stay in Kailua for great views of the Ko‘olau Mountains. Photo © Robert Linsdell, licensed Creative Commons Attribution.


Set on the Ka‘elepulu Stream, four blocks from Kailua Beach, Sharon’s Kailua Serenity Bed & Breakfast (127 Kakahiaka St., 808/262-5621, $80-95) has two rooms and one suite available with a continental breakfast. Casual and homey, the Blue Room has one queen-size bed, and the Poolside Room has a king and a twin bed. The suite is designed for a family of three to four. There are no cleaning fees. There is also a dog on the premises.

Just a few blocks away from Kailua Beach, Pillows in Paradise (336 Awakea Rd., 808/262-8540, $99-119) offers two units: a private one-bedroom unit and a spacious studio suite with king- and queen-size beds, perfect for families. Both units have private bathrooms and entrances, coffeemaker, refrigerator, microwave, and other kitchen items. A swimming pool graces the tropical garden.

The Sheffield House Bed & Breakfast (131 Kuulei Rd., 808/262-0721, $129-169) is just steps away from Kailua Beach and has two suites with private entrances, Mexican tile floors, wireless Internet, kitchenettes, and off-street parking. The Ginger Studio with Secret Garden sleeps two to three and has a tropical garden and fountain outside the entrance. The Garden Suite sleeps two to four and can be combined with the Ginger Studio to form a two-bedroom, two-bath rental. There are cleaning fees in addition to the rate and a complimentary breakfast on the first morning of the stay.

Located a half-mile from the beach, Papaya Paradise (395 Auwinala Rd., 808/261-0316, $100) has a large swimming pool, great views of the Ko‘olau Mountains, and a covered lanai for relaxing, reading, and enjoying the daily complimentary continental breakfast on. The rooms have wireless Internet, private entrances, private baths, two beds, and tropical furnishings. They also have beach accessories on hand to borrow.

Map of Kailua, Hawaii

Just south of Kailua in the Lanikai enclave, Hawaii’s Hidden Hideaway Bed and Breakfast (1369 Mokolea Dr., 808/262-6560, $145-195) has several suites surrounded by tropical foliage with private entrances, private bathrooms, kitchenettes, dining areas, lanai, wireless Internet, and laundry facilities. The Deluxe Studios each sleep two and offer a choice of king, queen, or twin beds. The Peacock Suite sleeps two to three and has a large lanai with an outdoor spa. The units can be interconnected, and there are additional cleaning fees of $55 per unit.

Lanikai Bed and Breakfast (1277 Mokulua Dr., 808/261-7895, $160-175) is 100 yards from Lanikai Beach. The Garden Studio has teak and bamboo furnishings, an outdoor dining area, and a king-size bed. The Tree House is a spacious upstairs two-bedroom suite surrounded by mature trees. Both units have high-speed Internet and kitchenettes.

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