Family-friendly holiday rentals in Waihee-Waiehu

Private Poolside Oasis & Ocean Views

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

Family · Indoor spaces · Air conditioning

The Blue Door on Church Street | Spacious Two Bedr

Enjoy Haleakalā views from this spacious two-bedroom upstairs retreat at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Features include a king Helix bed, queen Helix bed, full-size memory foam sleeper sofa, full kitchen, rainfall shower, AC, fast WiFi, Smart TV, parking for two vehicles, and a large private deck with outdoor dining and lounge seating. Walk to local cafés and restaurants, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui attractions

Kitchen · Indoor spaces · TV

Hana Nautilus- Ocean view 3 bed 2 bath family home

SUP 2019/0006 STHA20200001 Hawaii TA Tax:TA-081-974-0672-01 Hawaii GE Tax:GE-081-974-0672-01R Located in Hana, Maui this custom built 3 bedroom 2 bathroom ocean view house is situated on 2.8 acres of agricultural land. The land is abundant with seasonal fruit trees the guests may enjoy when available. The owners are delighted to offer helpful information so you can have a safe and enjoyable experience. Hana offers amazing adventures such as hiking, diving, swimming, surfing and stunning beaches

Family · Indoor spaces · Outdoor spaces

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.

Indoor spaces · Kitchen · Solo travel

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

Family · Kitchen · Walkability

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

Serene, Beachy decor. Awaken to Sunrise over Haleakala & North Shore, listen to surf and local birds, and watch the ocean and harbor action- Surfers, Kiters, Sailboarders, Kanaha beach from the secluded back yard. Relax in the hot tub and sauna. Very Central, but you’ll want a car or Uber to get to most places- Wailuku town is 1 mile. Hosts live on-site for needed assistance, otherwise allow guests to enjoy their peace and solitude during the evenings after the day's adventures. FAST Internet

Kitchen · Indoor spaces · Hospitality

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 12 years with over 1,500 five star reviews. BUT Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "The Jewel is extraordinary! The views are stunning! I’ve stayed in many Air B&Bs. I give her place my highest rating!" Btw, we have not raised our prices. The service fee now shows.

Indoor spaces · Kitchen · Checkout

Maliko Retreat

NOTE: This farm stay is not being phased out by County regulations. Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. This eclectic antique Hawaiian cottage is perched atop a scenic jungle gorge with breathtaking views in every direction. Open and breezy; attention to detail shines from every facet.

Family · Indoor spaces · Wi-Fi

Hana Ocean Palms Bungalow STHA2009-003

Hawaii Tax of 18.42% is included in the price. Our beautiful Island Style home in Heavenly Hana Hawaii is three hundred yards to a magical ocean pool and a one mile coastal walk to a magnificent beach. The house is open to nature, is fully screened, has hammocks and an ocean view. It sleeps six comfortably, is equipped with a full kitchen, and has an outdoor shower as well as a nice indoor shower and tub. The property is full of tropical fruits, flowers, bamboo, and palms

Kitchen · Family · Heating

Maui Private Suite Waena Inn 14

Enjoy a cozy 324 sq ft modern Ohana studio at Waena Inn in Maui with a kitchenette and private bath. Large windows showcase West Maui Volcano views and fresh breezes. Amenities include A/C, Wi-Fi, smart TV, and free parking. Centrally located between Maui’s west and east sides, 10–15 min from airport, beaches, and shops. Not a resort or beachfront—this is a peaceful, local residential stay ideal for an authentic island experience and easy island exploration.

Indoor spaces · Kitchen · Walkability

Malie at Haiku Garden Cottages Farm Sanctuary

Welcome to Haiku Garden Cottages, a licensed Farmstay and BnB on Maui’s North Shore (Permit BBPH2017/0002). Mālie is a charming cottage where you can sip coffee on the screened-in lanai, wander tropical gardens, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and peaceful indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, nearby beaches, hiking trails, local restaurants, and farmers markets.

Family · Kitchen · Backyard

The Art Estate, Haiku Maui Hawaii

Our spacious, open-floor-plan home has a contemporary style. The secluded 17-acre, lush, tropical estate has exotic varieties of Bamboo, Palms, Avocados, and various fruit trees. Located on the grounds is a private, functioning, award-winning art studio creating films, photography, video installations, and sculpture. If you are looking to explore, we are just a quick ten-minute drive to the best beaches on the North Shore!

Indoor spaces · Kitchen · TV