Family-friendly holiday rentals in Wailuku

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

Oceanfront Bliss Pool & Stunning Views Hono Kai C3

Kick back island style at this laid-back beachfront escape with a touch of luxury. Soak in epic ocean and Haleakala views right from your living room and lanai—perfect for whale and turtle watching or checking the waves. Fully stocked kitchen, comfy vibes, and all the essentials for easy living. Chill by the oceanfront pool, fire up the BBQ, or cruise down to stroll along the endless serene beach just steps away. Central spot close to Kahului, Kihei, Paia, and Kaanapali - surf, relax, repeat.

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.

Grnd Floor 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: travertine 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.

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.

GORGEOUS Oceanfront/Ocean View*FULLY Remodeled!

This beautiful 559 square feet 1 bedroom, 1 bathroom unit is located just steps from the glittering Pacific Ocean, and comfortably accommodates up to four people. This condo is located in the quaint harbor village nestled between Maalaea Bay and the West Maui Mountains. Enjoy the luxury of being miles from crowded resorts, yet convenient to all your most popular island activities. The Maui Ocean Center is next door, and a delightful outdoor center with shopping and dining opportunities.

Oceanfront Condo with Pool and Jacuzzi

Relax in this peaceful gem on Maui. Located on the ground floor, you can walk into the ocean from your back porch. You'll see Turtles on our little secluded beach, amazing sunrises and sunsets over Maalaea Bay, and Whales during whale season! Maalaea Banyan is the only property in the area that includes a pool and jacuzzi. Just 1/4 mile away is Maalaea Harbor featuring snorkel, SCUBA, and sunset boat trips, the world famous Maui Ocean Center aquarium, restaurants and gift shops!

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.

Turtle Cove Oceanfront Views Island Sands Resort

This rare ocean-front condo (LEGAL vacation Rental) is stunning! We call it a "Cruise ship view" cause you can't get any closer to the water than this! Listen to the sound of the ocean from the comfort of your home, while watching whales (Dec-April) and Hawaiian Green Sea Turtles frolicking all year long! Fully stocked, has A/C in living room and bedroom. Located a five minute walk from boats, Maui Ocean Center Aquarium, shops and restaurants at Ma'alaea Harbor!

Spacious 2BR | Huge Patio + Haleakalā Views

Enjoy Haleakalā views from this spacious 2BR villa at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Featuring a King and Queen bed, full kitchen, rainfall shower, and a private deck. Walk to cafés, shops, and theaters, or take a short drive to ʻĪao Valley, beaches, and top Maui attractions. Includes modern comforts, air conditioning, parking, and an on-site infrared sauna for a relaxing retreat away from the crowds.

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.