Family-friendly holiday rentals in Paia

Paia Surf Suite. Quiet beach access & walk to town

A private beach path 150m from your door! Walk to the surf! Less than 15 minute walk to the charming cafes of Paia town. Located at the rear of an ocean-front property on the beautiful North Shore, 5 minutes from world famous Ho.okipa. The rental contains 1 bedroom, 1 bathroom, living area & private lanai (patio). The kitchenette is equipped with mini-fridge, toaster oven and microwave. On the start of road to Hana, central to everything! NOT affected by Bill 9. Your booking is 100% secure!

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 ✔

Relaxing Upcountry Base for Haleakalā & Beyond

Unlike any other stay! The Romantic Rose Room of our historic Inn is a cozy retreat beneath Maui’s largest Norfolk pine. Guests come here to exhale, reconnect and feel the quiet healing of the land. Enjoy the gardens then head out for adventures to beaches, Haleakala or Hana-creating lasting memories along the way. Beach gear & stadium blankets (for Haleakala) are provided along with"brekky baskets" to start your day. I look forward to sharing this special soulful space with you. BBMPT20200001.

Kuau Plaza Paradise in Paia 3

Tucked away on Maui’s north shore, this cozy hideaway offers a relaxed, local vibe—far from the resort crowds. Just steps from Mama’s Fish House and Mama’s Beach, you’ll be close to some of the island’s most stunning and uncrowded spots. Ho’okipa Beach, a world-famous surf and turtle-watching destination, is just minutes away, and downtown Paia—with its eclectic shops and cafés—is only a mile down the road. If you're seeking an escape with true island character, this is your kind of place.

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

Spectacular Ocean Views • Private Studio• King Bed

Ocean View Studio • Private Lanai • Peaceful Upcountry Maui Retreat Wake up to breathtaking panoramic views stretching from Maui’s North Shore and Central Valley to the West Maui Mountains and majestic Haleakalā. Enjoy your morning coffee on your private lanai with Maui Tradewinds - breezy days, cool evenings and a peaceful side of Maui that many visitors never experience. Sugar Shack Maui offers an authentic island experience just minutes from everything.

Kuau Cottage

Clean, newly built 1 bedroom/1 bath with super fast internet and A/C. Situated in a quiet neighborhood in Kuau, away from the hustle and bustle of Paia but still just a short 1 mile car journey from the town. Kuau Beach and Mama’s Beach are both walking distance from the house and world-famous Ho-okipa Beach Park is just a 1-mile drive away. Kanaha Beach Park and Kite beach are about 15 minutes from the house. TVR Tax (10%) and GET (4%) included in price.

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.

Locally-Owned Eco-Friendly Condo on Road to Hāna

Kūʻau on Maui's north shore offers uncrowded access to unique beaches and the best proximity to Mama's Fish House, Pāʻia town, Road to Hāna, Haleakalā National Park, and Kahului airport. Designed with environmentalist principles, every detail has been mindfully chosen. This local family-owned small business proudly supports other local businesses. I welcome people of all backgrounds to connect with the natural environment and cultures of Maui.

Haiku Hideaway - Stand-alone 2 bedroom farm house

Our country farmhouse has a very unique feel with detailed craftsmanship (built by the owner). It’s a 2/1, 1000sqft open concept with a 500 sq. ft. covered deck off the living room and views of the ocean & mountains. We have goats and plenty of trees . We are 6mi to Hoʻokipa Beach Park, 10 min from Twin Falls, 6mi to Makawao & 9mi to Pāʻia. Quiet neighborhood and private. Come relax! TA-122-773-8112-01. GE-122-773-8112-01 BBPH 2021/0001

Paia Surf Condo

Classic Paia surf condo located on the first floor of Kuau Plaza centrally located on Maui's north shore. Your private patio leads out to a large communal lawn and palm trees. Mama's hidden beach is only a two min walk, Ho'okipa a two minute drive, a 5 minute drive to Paia town with unique shopping and great restaurants, and a 10 minute drive to Haiku. You are perfectly positioned for your trip to Hana or Haleakala Crater.