Top 9 Vacation Rentals in Maui, Hawaii - Trips To Discover (2024)

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Adorable Garden Gingerbread House - Makawao

One of the most popular Airbnb rentals in Hawaii and even the entire U.S., the Gingerbread House is a renovated 1930s studio cottage set along the northwest slopes of Haleakala in gated property. The lush 4.5 acres include many fruit trees producing coconuts, guava, mango, banana, passion fruit, and papaya, as well as an organic veggie start farm, all of which you’re free to enjoy. The Sacred Garden, located adjacent to your outdoor patio, has lily ponds, walking labyrinths, and meditation zones. Inside, there’s a small kitchenette, spacious bathroom, and high cathedral ceilings with a huge window looking out at the enchanting greenery.

Pinnacle Escape From Reality - Haiku-Pauwela

The Pinnacle Escape From Reality is an aptly named luxury hilltop estate that offers an unobstructed 180-degree view of the Pacific, Molokai, the Maui mountains, and the central valley. To the east, you’ll see Haleakala come into view. Spread over 3,100 square feet, it includes three bedrooms and four bathrooms along with a wide range of amenities like a gourmet kitchen, flat-screen TV with TIVO, a DVD player, and smaller TVs in both the kitchen and master bath. You’ll have free Wi-Fi, central a/c, and stereo wired throughout the house, even on the lanai.

Mana Hale Vacation Rental - Kihei

This gorgeous rental is tucked within a garden sanctuary, surrounded by fruit trees and tropical flowers, while the ocean and beaches ideal for swimming are just a mile away. Complimentary beach chairs and a large cooler are provided for your days on the sand. The home accommodates up to five guests in two bedrooms and includes a propane grill and a fully stocked kitchen, although there are many restaurants nearby when you want to dine out. Air conditioning, a washer/dryer, and Wi-Fi are included too.

2-Story Wailea Townhome with Ocean Views

This two-story townhome for up to six sits within the resort community of Wailea near one of the island’s most beautiful beaches, Makena Beach. It has two private lanais which can be accessed from both bedrooms while boasting awe-inspiring garden and ocean views. There are lots of high-end amenities and all the essentials like a fully-equipped kitchen, Wi-Fi, two large flat-screen TVs, and a full-sized washer/dryer. Beach chairs, pool noodles, boogie boards, and beach towels are supplied too for enjoying the complex’s two pools or the beach.

Eco-Friendly Beachfront Retreat - Hana

This three-bedroom beachfront home can accommodate up to eight guests, providing an eco-friendly stay within walking distance of Hana Bay, the beach, shops, and eateries. It’s close to everything, with other beaches and hiking trails easily reached via a short drive. The vast yard includes edible landscaping with berry bushes, orange and lime trees, turmeric, ginger, taro, and herbs, while inside, you’ll have an open concept living room, kitchen, and dining area, plus a downstairs family room area with a juice bar and extra refrigerator. The covered lanai upstairs is a popular hangout overlooking the ocean, while the large back deck provides outdoor dining and stargazing. A downstairs covered patio also has a nice ocean view.

House with Pool & Spa, Minutes to Beach - Wailea

This beautiful private three-bedroom home in the Wailea area sits on a one-acre property, close to beaches, golfing, shopping and dining. You’ll have your own private pool and spa, beach gear, and fantastic views of Lanai, Kahoolawe, Molokini Crater, and Molokai. From the main floor deck, you can look forward to the island’s stunning sunsets at the end of every day. Inside, 40 feet of glass face the ocean and pool. A fully equipped indoor kitchen and outdoor BBQ, free Wi-Fi, a flat-screen TV with a DVD player, and a washer/dryer, are all included along with beach chairs, umbrellas, and water toys.

Only 10 Steps From Beach - Kihei

As the name belies, this oceanfront condo is just steps from the beach and ocean, typically perfectly calm and ideal for snorkeling with sea turtles and colorful fish. The sand of Sugar Beach is just like powdered sugar, wonderful for sinking your toes into. In the winter, you might even hear the songs of whales while you’re underwater. It includes one bedroom and can accommodate up to four in two beds while offering views of the Pacific from the high-end kitchen and living space as well as the balcony, a perfect spot for morning coffee and sundowners.

2-Bedroom with Ocean Views, 5 Minutes From Beach - Kapalua

This family-owned villa accommodates up to six guests in two bedrooms, with the master boasting a separate lanai that overlooks the ocean. Enjoy the plush furnishings that make it easy to relax with a dazzling 180-degree-view of the Pacific out to Molokai. There are hand-carved furnishings, a kitchen with granite countertops and new modern appliances, air conditioning, and three HDTVs with cable. You’ll have high-speed Internet, an iPod dock, and even four land-line phones with free long-distance to U.S. and Canada.

3 Bedroom Home in Paia Town

Located in the north shore town of Paia, a walkable town away from the high-rise resorts while being the area’s hub for wind and wave sports, this is a rental for enjoying more authentic Maui. You’ll find funky shops, eateries, galleries, and a great natural foods grocery store while being centrally located for driving the road to Hana or to the top of Haleakala, which rises 10,000 feet above sea level, the top spot for catching a sunrise on the island. The home is traditional Hawaiian style, with a peek-a-boo view of the ocean. It has a/c throughout and offers three bedrooms, a full kitchen, an outdoor washer and dryer, and a covered lanai ideal for cookouts. Complimentary boogie boards, snorkels, masks, beach chairs, and a cooler are all provided too.