San Francisco, From $108 a Night
This festive hotel package is valid over the holidays and includes ice-skating at Union Square.
21. Blue Horizons Bed and Breakfast (3894 Mahinahina St., Lahaina, HI 96761; 800/669-1948, maui.net/~chips) offers four upscale rooms (three with private entrances), views of the ocean from a large lanai, a lap pool, and a location between Lahaina and Kapalua, within a short drive of Lahaina's action. Rooms start at $89.
22. Garden Gate Bed and Breakfast (67 Kaniau Rd., Lahaina, HI 96761; 800/939-3217, gardengatebb.com) is a large, modern, peach-colored home with spacious tropical garden complete with umbrella tables, its own stream and bridge, and three suites bathed in cream colors. It's located just one block from the ocean and Wahikuli Wayside Park. Rooms start at $79.
23. HalE Ana (1695 Olinda Rd., Makawao, HI 96768; 808/572-2508, haleana.com) is a good choice for those who don't need to be near the water and prefer the cooler climate of Maui's Upcountry on the slopes of Haleakala. It has two upstairs rooms in a gorgeous, modern home with huge, two-story windows in the living room looking on to the stunning views of West Maui. The home's two acres include flower and food gardens, and there's also a spa and sauna on premise. Rooms start at $85.
24. Hale Kokomo Bed and Breakfast (2719 Kokomo Rd., Haiku, HI 96708; 808/572-5613, bbonline.com/hi/kokomo) is located 1,400 feet above sea level in the lush, north-shore area of Haiku, and this 1927 Victorian-style villa offers four bedrooms and a living room with an open fireplace, as well as gardens. Rooms start at $50.
25. Hana Maui Botanical Gardens Bed and Breakfast (470 Ulaino Rd., P.O. Box 404, Hana, HI 96713; 808/248-7725, virtualcities.com/ons/hi/m/him4501.htm), in the serene old town of Hana on the island's eastern shore, is comprised of two cottages with kitchens and lanais on a 27-acre farm with botanical gardens open to the public (you can even pick your own fruit). Rooms start at $75.
26. House of Fountains (1579 Lokia St., Lahaina, HI 96761; 800/789-6865, alohahouse.com) touts itself as "the most Hawaiian B&B on Maui" and is tucked away behind Lahaina in the lower slopes of the West Maui Mountains. Its six rooms include koa wood furniture, Hawaiian quilts, and handmade Polynesian arts and crafts, and there's a pool and hot tub. Rooms start at $95.
27. Kailua Maui Gardens (P.O. Box 790189, Paia, HI 96779; 808/572-9726, kailuamauigardens.com) is along the popular "Road to Hana," with three cottages among nearly two private acres, including a pool, two spas, and a barbecue area. Rooms start at $95.
28. Old Lahaina House (P.O. Box 10355, Lahaina, HI 96761; 800/847-0761, oldlahaina.com) is perfect if you want to be just two blocks from the town of Lahaina and across the street from a local surf spot. The two-story white home has a large pool and courtyard, and the owners can help secure cheap car rentals for guests. Rooms start at $69.
29. Penny's Place Inn Paradise (1440 Front St., Lahaina, HI 96761; 877/431-1235, pennysplace.net) is a two-story, plantation-style building (with a Victorian turret and wide, wraparound porches) right in the heart of the action on Front Street in Lahaina. Rooms start at $88.
30. Spyglass House (367 Hana Hwy., Paia, HI 96779; 800/475-6695, spyglassmaui.com) couldn't be closer to the water (30 feet from a secluded shore), and the three houses with eight rooms are situated around a brick-top courtyard with sunken, tiled Jacuzzi. You can rent by the room or the house (each building has three bedrooms, two bathrooms, full kitchen, living room, and expansive oceanfront lanai). Rooms start at $90.
Molokai
31. Ka Hale Mala (P.O. Box 1582, Kaunakakai, HI 96748; 808/553-9009, molokai-bnb.com) is a 900-square-foot apartment with four rooms on the bottom floor of a beach house, with a garden and lanai, within walking distance of the beach, and on the edge of a wilderness area. Hawaiian breakfasts include taro, poi, or purple sweet potato pancakes. Rooms start at $80.