Family-friendly holiday rentals in Maui County

Private Hot Tub + Pool Access + AC - Star Lookout

Dreaming of the perfect jungle honeymoon hideaway or retreat? Set amidst a mature coconut grove, (with your own hammock) this private cottage puts you in a romantic world of your own. We have that 'away-from-it-all' feeling but it's only a 20 minute drive to beaches and fabulous restaurants! A perfect romantic hideaway or artist's retreat! ☞ ★Jump Start to The to the Road to Hana! ✔ ☞ ★NEW COLD CENTRAL AC ✔ ★Private Hot Tub ✔ ★Swimming Pool ✔ ★King Bed ✔ ★Sunrise View ✔ ★Outdoor Shower ✔

Beach · Hiking · Hospitality

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.

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.

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.

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.

Solar Cottage With Privacy & Panoramic Ocean Views

Entabeni Cottage sits above the Road to Hana overlooking the Pacific Ocean on the north shore of Maui, Hawaii. Entabeni Cottage is a fully-equipped, 830 square foot home, powered by the sun and beautifully situated on a gorgeous 6.25 acre tropical flower farm. Enjoy ocean views from your bed, kitchen, lanai (covered deck), & private yard. The Kristiansen's offer guests fresh eggs and vegetables from the garden when ready for harvest. License & Permit: BBHA 2013/0006 and SUP2 2012/0011

Hospitality · Outdoor spaces · Cleanliness

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.

Spacious garden oasis next to Maui's best beaches!

Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ a pull-out sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Soak in paradise on two garden patios!

Hana Maui Luxury Elua Cottage

OCEANFRONT SPLENDOUR IN PERFECT HARMONY WITH NATURE This beautiful cottage is set directly on the bluffs of Hana Bay surrounded by beaches and black-lava landscapes. Hana Maui Luxe Elua Cottage is perfectly situated for all kinds of island adventures on the Eastern tip of Maui. The spirit of Old Hawaii lives on in Hana from its long-held traditions to the inspired natural beauty of this idyllic retreat. This cottage has been extensively renovated with updated finishes and furnishings.

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

Across Beach! Ground Floor 2 bed 2 bath, sleeps 6

2 bed/2 bath ground-floor condo with cold split-unit AC and AC in every room. Fully equipped for home-cooked meals and beach days (towels, coolers, snorkel gear, boogie boards & chairs included). Walk 3 mins to Maui's top-rated Kamaole and Charley Young beaches, shops, and dining. Includes 2 dedicated parking spots just seconds to either door entrance (no stairs!) and access to an exclusive gated pool, jacuzzi, sun loungers and gas BBQ grills. WELCOME TO PARADISE!

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.