Family-friendly holiday rentals in Kahului

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

Walking on Sunshine Maui ~ Remodeled and By Beach!

~ Now Open: March/April🤙😎 Walking on Sunshine, #251, is hosted by Tracy O’Reilly, a licensed realtor on Hawaii who has been w/Airbnb since 2009 & has earned SUPERHOST status 46+ times w/1000s of 5 Star Reviews! ~ The beach+whale center is directly across the street. Pool, jacuzzi, tennis court, BBQ area, laundry center all onsite. ~ If your dates aren't available or if you’re traveling with a group, contact Tracy on Airbnb to see if it's possible to book 1 of 16 Maui Airbnbs she manages.

Romantic Bliss Maui: Corner Penthouse, By Beach

~ Now Open: March/April🤙😎 Romantic Bliss is hosted by Tracy O’Reilly, a licensed realtor on Hawaii and SUPER HOST who has been w/Airbnb since 2009 & has earned SUPERHOST status 46+ times w/1000s of 5 Star Reviews! The beach and whale center are directly across the street. Pool, jacuzzi, tennis court, BBQ area, laundry center all onsite. This is the Corner Penthouse w/ XL lanai ~ If your dates aren't available or if traveling with a group, contact Tracy on Airbnb as she manages 16 condos.

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, 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: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

Tropical & Serene Garden Vistas

Newly remodeled 1 bedroom, 1 bath ground floor condo. Located directly across from the beach in warm & sunny Kihei. Nestled in the exclusive and desirable Kihei Resort, you will be embraced in the lush & tranquil landscaping. We provide beach chairs, umbrellas, luxury beach towels and a cooler to ensure your beach day is set for success. Our kitchen is fully stocked, ready for the home chef to prepare any meal, or for the master baker to tackle any recipe. Incredible dining options close by!

Makani A Kai B12 beachfront Maui, pool, a/c, w/d

Halerentals MAK B12 is a completely renovated Makani A Kai condo with high-end RH furniture, quality white cotton sheets, Sonos audio, marble shower, gourmet kitchen, motorized shades, & A/C in every room-- steps away from 3 miles of undeveloped Sugar Beach! Bright spacious 2nd floor 2bed/2bath condo with vaulted ceilings, stocked kitchen, and views of the bay, Haleakala volcano, and Haycraft Park. Great spot for swimming, SUP, snorkeling, and surfing-- amazing value for families or couples.

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.

Awesome Maui home. Discounted stays. Includes tax

A/C throughout. Work desk with dependable wi-fi. SMart TV in living area. Cable TV in master bedroom. Grass area off lanai. Walk to the beach, stores, restaurants, the park or bus stop. Full kitchen, W/D, 2 queen beds and 1 queen sofabed, 4 beach chairs, 4 beach towels, a beach umbrella and travel cooler, Pak-n-Play, Booster Seat, 2 pking spaces. This condo is comfortable and well-eqipped for a wonderful stay and vacation on Maui. New pool and jacuzzi.

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.

Waena Inn 11– Newly Renovated 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.