Family-friendly holiday rentals in Paia

Ho'okipa Hideaway - Walk to Restaurant/Store

Ho’okipa Hideaway is the ideal home base for all of your Maui adventures. This private studio includes a modern kitchenette, newly remodeled bathroom, and a screened-in lana’i (The Zen Den). It offers its own gated, private entrance, a large, private, tropical garden, and a designated parking spot. Walk to "Baked on Maui" for breakfast and lunch, a little market, and several local surf shops. We have been licensed by the County of Maui for 11 years and maintained a 4.9-5.0 rating on Airbnb.

★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✔

North Shore Maui Beach Condo - Kuau Plaza Paia

Great location overall. Located near Mama's Fish house and Less than a mile away from world famous windsurfing/surfing beach, Ho'okipa Beach. Renovated 1 bedroom, coveted end unit with upgraded two quiet AC units. Clear view of upcountry, the east Maui mountain, from condo entrance. Cool mellow vibe. Transportation is also available for rent. Inquire directly for any questions or concerns. Check out my car on Turo! https://turo.com/us/en/car-rental/united-states/paia-hi/ford/mustang/1058537

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.

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

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.

Hunter Hales Hoku cottage, Haiku, Maui

Hunter Hales "HOKU" is one of the two identical 810 sqft cottages on one half acre lot privately located just behind the Haiku Town center. Conveniently located at the start of the Road to Hana. Enjoy the quiet laid back life style of a classic Hawaii country town. You will feel so at home within the detailed cottage, equipped with everything one would possibly need while on vacation. This is local Maui vacationing at its best! TA-192-286-5152-01 STPH 20150004 TMK (2) 2-7-003:135

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.

Paradise In Paia 2

This lovely, recently updated condo on Maui's beautiful North Shore is located at Kuau Plaza in Paia. If you are looking for a great location, steps from the beach and want to experience the real Maui, look no further. This first floor unit offers an expansive lawn with a direct path to the beach. The updated decor is mid century modern with tropical accents to honor the building’s history which is reminiscent of Old Hawaii.

PAIA HALE Walk to beach and town

This sweet cottage sits on a flag lot, gated and fenced, shared with my 2 bedroom cottage. Parking is directly in front of the cottage. New kitchen as of July, 2025. There is a nice outdoor area with table, chairs and barbecue. Coolers and beach chairs are also provided. (Please note, I only advertise or book this condo through Vacation rental sites. If someone has approached you to book this directly, it is a scam.)

Peaceful and Spacious; North Shore Maui

New, spacious two-bedroom home in Ha'iku, Maui (Permit STPH20200003). With beautiful ocean views and peaceful surroundings, located on the Northshore of Maui, this is the perfect place to stay to explore the Road to Hana, the Northshore, and upcountry Maui. Perfect for two couples or a family, you'll have everything you need to explore the island and a peaceful living area to relax following a day of adventuring.