Family-friendly holiday rentals in Maalaea Bay

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.

Kitchen · Indoor spaces · Beach

Beautiful Oceanfront Condo- Great View, A/C,Wi-Fi

The convenient location in Maalaea leaves you minutes away from beautiful beaches, restaurants, and all Maui destinations. An open layout consisting of 1 bedroom and 1 bath gives an expansive feel to this exquisite unit. Central A/C. Luxury upgrades include: luxury plank flooring, custom kitchen and bathroom cabinetry, granite counter-tops, new stainless appliances, stone flooring and stone/glass shower. Meticulously maintained grounds along with a refreshing swimming pool and grilling area.

Family · Kitchen · Hospitality

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.

Family · Kitchen · Walkability

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

Family · Kitchen · Beach

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

Family · Indoor spaces · Cleanliness

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.

Kitchen · Family · Location

Maalaea Banyans 303 oceanfront, pool, hot tub, w/d

Halerentals MB 303 is a lovely, centrally located, and renovated 3rd floor Maalaea Banyans condo. Gorgeous views from the spacious balcony, living room, and kitchen. Beautiful landscaping, pool, and hot tub steps from the ocean with a tiny beach for snorkeling, paddle boarding, and swimming. Cool AC throughout. Easily walk to nearby restaurants and shops at Maalaea Village, or stroll down the 3+ mile long undeveloped part of Sugar Beach. Amazing value for families and couples. Aloha!

Indoor spaces · Kitchen · Condition

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

Family · Indoor spaces · Quiet

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.

Family · Indoor spaces · Checkout

Pickleball, Saltwater Pool, King Bed, AC, Ground

NO GUEST FEES – We Pay Them (taxes and cleaning still apply)! Escape to paradise at Rainbow Island Retreat! This tropical, professionally designed ground-level condo is perfect for couples, families, or groups of 4. Enjoy extra outdoor space, steps from the saltwater pool, tennis/pickleball courts, and Charley Young Beach across the street. Beach and child gear provided for a comfortable, fun, and memorable stay.

Kitchen · Family · Condition

Charming Hoku Pauwela Breathtaking ocean views!

Located on the north shore of Maui, Hoku Pauwela (Maui County B&B Permit# BBPH 2019/0002 and Hawaii State TAT # TA-036-968-8576-01) is the ideal location from which to experience the north shore, upcountry, Haleakala crater, and the epic drive to Hana. Spacious, quiet, and family-friendly, you'll have all you need to explore Maui and a peaceful living area to relax in after a day of adventuring.

Kitchen · Indoor spaces · Beach

2BR Oceanview | Beach, Pool, Hot Tub, AC, Sleeps 5

Experience island living in our top-floor ocean-view condo in Kihei. Wake to ocean breezes and panoramic views. Recently updated with stylish touches, it offers comfort and charm for all. Enjoy whale watching in season and year round sunsets from the private lanai. Just steps from the beach, it's a serene escape—perfect for couples, friends, or families seeking a memorable Maui getaway.

Family · Kitchen · Hospitality