Family-friendly holiday rentals in Maui County

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.

Oceanview Cottage away from heat! w/ County Permit

Closest Airbnb to Haleakala National Park & Road To Hana. Away from 100 degree heat & traffic & yet still close to food & market! Private Cottage on 2acres of orchard on Haleakala, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Two master suites with ensuite Full Baths. For past guests whom love this home, this AirBnB ends on 12/31/26. Hawaii Supreme Court ruled no more short term rental in agriculture lands.

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

Relax & enjoy stunning ocean & sunset views, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, two-story oceanfront cottage with a large covered lanai. This no-smoking cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore, or unplug & relax. You will enjoy blue ocean & beach views, colorful sunsets, breezes, tropical birds, waves, and whales in the winter.

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Ocean View - Private Cabin

NOTE: 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. Located on a working coffee plantation and food forest, this restored cabin is private but close to lots of upcountry activities. Kitchen, ocean view, open concept, great lanai spaces, plenty of off-street parking, access to private hiking trails.

Adorable Gingerbread House Farm Stay, Makawao

This LEGALLY PERMITTED Farm Stay has the lush beauty and privacy,, without the drive to Hana! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. Seasonal stream in the back yard. Simply BEAUTIFUL! We gave 8.5 acres of diversified farm-fruit, water lilies, 10,000 sq ft greenhouse) Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

The Farm Cottage -At Olamana Organics

The farm cottage is set at the top of our 5 acre exotic fruit farm. Enjoy your stay by touring the property and relaxing in our cozy home away from home. The cottage is equipt with everything you'll need without the clutter. From the living room, enjoy a view of the ocean, fruit trees, and tropical flowers. Listen to the birds chirp in the morning, and watch the sky turn colors as the sun sets. Our accommodations are licensed with the State of Hawaii. Our license number is BBHA 2020/0001

Hale Leialoha (BBPH 20 17/00 04,SUP 20 17/00 10)

Hale Leialoha (GE-046-437-3760-01, TA-046-437-3760-01) is a beautiful Hawaiian style cottage located in "upcountry" Maui. Our Cottage is permitted for a total of 4 adults and up to 6 people. The cottage easily fits a family of 6 (4 adults & 2 children or 2 adults & 4 children or 3 adults & 3 children) (License # BBPH 2017/0004, SUP 2017/0010) As our guest, you will enjoy the modern finish and conveniences as well as a large roomy covered deck amidst the casual feel of old Hawaiiana.

<2 min to beach! Ocean view w/ AC

This updated, partial oceanview, modern 1 bed 1 bath condo comes equipped with a fully set up kitchen, California king sized bed, full size washer/dryer, TV, beach gear, internet, shared jacuzzi and pool, and (NEW) AC in the bedroom! Enjoy watching the whales during season, viewing the Maui sunset, and relaxing with a beverage and a book on the large lanai in the front of the condo. Located in North Kihei across from Kalepolepo Beach Park, this small complex is a peaceful Maui gem!

JJ’s Hāna Hale - Farm Style Cottage STHA2021/0001

Forget your worries in this spacious serene space. Private air conditioned one bedroom cottage located on a 6 acre farm that is home to many rescued animals. A second bedroom can be made available for a fee please inquire prior to booking. Have as little or as much interaction as you wish. A fully equipped kitchen with a gas stove, full bathroom, a comfy bedroom a spacious living room w Smart TV and separate dining area. Wifi is also provided. Bikes available for two.

Kalani at Haiku Garden Cottages Farm Sanctuary

Welcome to Haiku Garden Cottages, a licensed Farmstay and B&B on Maui’s North Shore (Permit #BBPH2017/0002). Kalani is a charming cottage where you can sip coffee on the lanai, wander garden paths, harvest seasonal fruit, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and relaxed indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, beaches, hiking trails, restaurants, and farmers markets.