Family-friendly holiday rentals in Wailuku

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.

Makani A Kai A9 romantic beachfront Maui, pool,a/c

Halerentals MAK A9 is a romantic and newly renovated beachfront condo, centrally located for day trips around the island, and off the beaten tourist path. Cool A/C in every room and smart home controls-- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 1bed/1bath condo- with fully stocked kitchen, new 75" SmartTV and views of the beach, bay, & Haleakala volcano. Ideal for swimming, paddle boarding, snorkeling, and surfing-- amazing value for families and couples.

2B/2B Cottage/Cozy/Central/Private/Historic town

2B/2B cottage, in the heart of Maui, in historic Wailuku town... home of the famous Iao theater and minutes from Iao Valley National Park & the famed "Needle Mountain". Private, fully furnished, and equipped with all amenities needed for a comfortable short-term stay. Easy access to Beaches,Airport & all parts of the island within a 10–30 minute drive. It's great for business travelers doing business in Wailuku, Hikers, Bikers, & true Hawaiiana- seeking tourists. Check out Wailuku First Friday!

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

Serene, Beachy decor. Awaken to Sunrise over Haleakala & North Shore, listen to surf and local birds, and watch the ocean and harbor action- Surfers, Kiters, Sailboarders, Kanaha beach from the secluded back yard. Relax in the hot tub and sauna. Very Central, but you’ll want a car or Uber to get to most places- Wailuku town is 1 mile. Hosts live on-site for needed assistance, otherwise allow guests to enjoy their peace and solitude during the evenings after the day's adventures. FAST Internet

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.

Oceanfront Kihei Condo Free SUP & Resort Pools!

This beautifully appointed 800 sq ft ground-floor condo features free paddleboard (a $50/day value) just 200 steps from sand. Enjoy resort-style amenities including a sparkling pool, soothing hot tub, kiddie pool, and pickleball courts nearby. Marvel at whale sightings (Dec-Apr) from your lanai or kitesurfing from shore. Stay productive with blazing 500 Mbps fiber WiFi and unlimited AC. We provide beach gear, parking, aon-site laundry. Our prime Kihei location offers the ultimate Maui escape

Mermaid Cove Oceanfront Views! 2 bdrm 2 bath

This lovely LEGAL vacation rental condo, overlooking the beautiful Ma'alaea bay, is stunning. 180 degree views, sweet sea breezes, and lullaby of the ocean! We offer A/C, as well as ceiling fans, fully stocked kitchen, pool, W/D, a short walk to the restaurants, shops and boats of Ma'alaea harbor and long, empty beach. The whales play just outside your lanai all winter and the sea turtles are visible all year long. You literally cannot stay any closer to the ocean without being on a boat!

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.

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.

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.

1929 Restored 1BR Plantation Home | Walk to Town

Experience authentic Maui at The Blue Door on Church Street, a renovated 1930s plantation home in historic Wailuku. This one-bedroom villa features a King-sized Nectar bed, memory foam sleeper sofa, spa-like bath, and a fully equipped bar area. Enjoy the on-site infrared sauna and walk to cafés, restaurants, and shops. Centrally located near ʻĪao Valley, beaches, and top Maui attractions—your perfect base for adventure and relaxation.

Unit 14 Waena Inn - Maui Private Suite

Enjoy a cozy stay at this 324 sq ft modern Ohana studio apartment in Maui, featuring a small kitchenette and private bathroom. Large windows offer beautiful views of the West Maui Volcano and the warm Hawaiian breeze. With amenities such as A/C, Wi-Fi, smart TV, and free parking, it's centrally located where the west and east sides of Maui meet, providing easy access to stunning beaches and the airport within a 10-15 minute drive.