8 Best Places To Rent on Maui for Spotting Whales This Winter
Rates starting at $799; Book it!
Tucked in historic Paia Town, where locally-owned surf shops and restaurants reign, this three-bedroom (king, queen, and two twin-size bedrooms) beachfront bungalow dubbed The Beachcomber sits at the end of a white-sand beach, straddling privacy and convenience. The Beachcomber’s decor, a nod to Paia’s past as a plantation village, blends contemporary amenities and rustic hues seamlessly, while offering guests modern upgrades like Apple iTV. Hideaway highlights include an ocean-view hot tub and daily maid service thanks to its affiliation with nearby Paia Inn.
Rates starting at $439; Book it!
A luxe guesthouse perched on the slopes of Haleakala above the popular Wailea resorts, this rental offers unparalleled views of the ocean. A private outdoor hot tub and 300 square feet of lanai space with 180-degree views serves up the perfect setting for spotting spouts. With only one bedroom and 1.5 baths, it’s the ideal getaway for couples seeking secluded romance on the Valley Isle.
Rates starting at $617; Book it!
The only luxury missing in this seaside escape is the “press for champagne” button. The private oasis, which is built to accommodate eight in Lahaina, offers guests ocean views from the comfort of a custom backyard pool surrounded by palms and fruit trees. The real treat comes in the form of an outdoor fire pit, perfect for watching stars while listening to the ocean lap against the sea wall below.
Rates starting at $179; Book it!
This cozy one-bedroom condominium on west Maui is tucked within the Kuleana Resort. It's decorated in traditional Hawaiian decor, but the real treat is the view from the living room couch, where turquoise water meets the pristine Kahana coast. Seven acres of resort property feature tennis courts and one of Maui's largest heated swimming pools surrounded by lush tropical gardens. Nearby bars and restaurants are walkable from the condo's front door. Stay in one night to watch the sun sink behind neighboring Molokai from the private balcony.
Rates starting at $2,280; Book it!
Operated by a Maui local, this palatial property in Lahaina offers panoramic ocean views that extend to neighboring islands Lanai and Molokai and can accommodate up to 12 comfortably. Whales can be spotted from two stories of glass lined-lanais, the comfort of the king size beds in four of the oceanfront master suites, or while sitting in the living room, where a retractable floor-to-ceiling glass wall slides away to create an indoor/outdoor oceanfront living and dining experience.
Rates starting at $625; Book it!
Live your best out-of-office life in this Lahaina townhouse rental that boasts a California king-sized bed, full kitchen, outdoor dining space, and roll-away slider in the living room which has views of endless cerulean water. Situated steps from the beach with three stories to accommodate up to eight guests, the outdoor lanais (yes, there are two!) are ideal spots to enjoy a morning cup of coffee while whales breach in the background. Have your phone handy for that perfect Instagram snap! #OOO
Rates starting at $3000; Book it!
Book this spacious oceanfront home, and bring the whole family. The six-bedroom, 5.5-bath home sleeps 15 with plenty of room for each guest to stretch out and relax when they're not swimming with turtles by the seawall, soaking in the hot tub, or taking in ocean views while whales swim by. This beautiful home is only a short walk to Front Street, a seaside mecca of shops and eateries capped by the Lahaina Harbor. No one should utter the words "I'm bored" with so many things to see, do, and experience.
Rates starting at $449; Book it!
Screensavers come to life in this idyllic hillside home in Maui’s Launiuopoko community, where the only important daily decision is where to watch the whales—lounge chair, lanai, or pool? With two bedrooms and two baths that can house up to six people, this rental also features a one-of-a-kind outdoor kitchen with BBQ, sink, full refrigerator, and plenty of seating for guests. When you're finished watching the water for breaching whales, you're only minutes from popular Launiupoko beach and nearby Lahaina Horse Stables.