Holiday rentals in Waikapu

Top guest favourite

Guest favourite

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

Top guest favourite

Guest favourite

Poolside Ocean View Retreat- Private Guest Suite

Escape to a relaxed tropical retreat in private villa-style suite featuring its own entrance, ensuite bathroom w/ natural stone shower, coffee station, mini fridge, & outdoor bistro seating. Guests also enjoy access to our lush shared pool area and shared kitchen spaces, creating a boutique island experience designed for comfort, connection, and relaxed Maui living. Centrally located & great for exploring all Maui has to offer. Great hikes and beaches nearby! Maui County Permit BBWK 2019/0003

Top guest favourite

Guest favourite

Ke Kīhāpai Bed and Breakfast

Ke Kīhāpai translates to "small farm" and sits on the slopes of Haleakalā mountain. Panoramic views of the West Maui Mountains below and the top of Haleakalā, a 25 minute drive to the entrance of Haleakalā National Park. At night, witness a galaxy of stars. Ke Kīhāpai is listed as a permitted B & B. Breakfast foods will be provided by the host. We are a local Hawaiian family, born and raised in the islands and steeped in the knowledge of our culture. We love to share what makes Maui so special.

Top guest favourite

Guest favourite

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

Top guest favourite

Guest favourite

Sweeping Panoramic Ocean Views - Private Ohana

Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Oceanfront, Ground Floor Condo Steps to Ocean

The perfect Maui vacation awaits you in this oceanfront ground level condo located on the Kana'i A Nalu property centrally located on the island in Ma'alaea Bay. Watch whales (Dec-Mar) directly from the lanai as they play in the harbor and then fall asleep at night to the waves outside the bedroom window. Discover the longest stretch of beach on Maui - 2.5 miles of secluded white-sand stretching from the condo towards Kihei with views of nearby islands of Kaho'olawe, Molokini and Lanai.

Top guest favourite

Guest favourite

Romantic and Private Cottage and Gazebo for two!

Romantic, Private, a Sanctuary, beautifully decorated, local charm and sleeping to the sounds of Wailuku River are a few things our guests say about our Inn. An American Whirlpool hottub is our newest feature amenity along with the air conditioning, washer/dryer, full kitchen and a large shower in your private bathroom. A king Size bed, Wifi, barbeque grill, television, fans beach towels are standard amenities. The detached Gazebo is perfect for reading, meditating, or just doing nothing!

Top guest favourite

Guest favourite

The Blue Door on Church Street | Vintage One Bedro

Stay in a restored 1929 plantation-style retreat at The Blue Door on Church Street in historic Wailuku. This private one-bedroom space features a king Helix bed, queen memory foam sleeper sofa, high ceilings, original wood details, kitchenette, rainfall shower, soaking tub, AC, fast WiFi, Smart TV, parking, and access to a shared infrared sauna. Walk to cafés, restaurants, shops, yoga, and the ʻĪao Theater, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui adventures.

3BR spacious Condo with Ocean View in top location

Enjoy ocean views and island living from this spacious 1,400 sq ft 3-bed/2-bath condo in the heart of Kihei. Located directly across the street from the beach, you can watch whales from the lanai or relax by the pool and BBQ area. Shores of Maui offers easy access to Kihei’s best beaches, shops, and restaurants, all within minutes. A perfect home base for families and groups looking for comfort, convenience, and the South Maui lifestyle.

Maile Bungalow- County Licensed

Maui County License: BBPH2009/0012 (taxes included in rate) Lovely cottage with ocean and country views, surrounded by tropical flowers and fruit trees located in a small quiet and peaceful neighborhood in Ha'iku. The cottage is off the road and the neighborhood has no through traffic. Walking distance (15min) to Ha'iku's Market Place and bus stop. The cottage is well equipped with all amenities you need to feel home.

Paia Family House

Walk to the beach and to everything in Paia Town. Walk to cafes, restaurants, Mana Natural Foods market and galleries. Get to world-class windsurfing, kiting, & surfing in a jiffy. Plenty of room for gear storage. Enjoy! *NOTICE: OUR NIGHTLY RATE INCLUDES A MANDATORY HAWAII STATE OF 18.712% ON ALL RENT starting January 1st, 2026. A weekly mid-stay clean is mandatory for stays of 2 weeks or longer. STPH 2018/0002

Milo Surf Cottage

4 bedroom, two bathroom, oceanfront cottage, sleeps 8, one rental group at a time. Relax in this charming 2 story house or under the palm trees. Enjoy the surf or nearby swimming beach. Minutes away from world famous Ho'okipa Beach Park. The property has the perfect blend of privacy and seclusion yet within easy walking distance to shops and restaurants in quaint downtown Paia.