Family-friendly holiday rentals in Wailuku

The image captures a serene beachfront location with clear turquoise waters and a sandy shore. Lush palm trees line the beach, contrasting against the distant green hills and blue sky adorned with soft clouds. The property is indicated by a directional marker, emphasizing its prime location.

4.96 out of 5 average rating, 166 reviews

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.

4.89 out of 5 average rating, 510 reviews

An open living space features a comfortable bed with soft blue linens, a stylish fold-out loveseat, and a large area rug. A fully equipped kitchen with wooden cabinets and a breakfast bar is visible, complemented by natural light from nearby windows.

Guest suite in Wailuku

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

A lanai space features a table and chairs with a view of the ocean and distant islands. Tropical foliage decorates the foreground, including palm trees. The backdrop includes a clear sky with scattered clouds and a parking area adjacent to the property.

4.95 out of 5 average rating, 165 reviews

Cozy Retreat With Ocean Views & Luxury Amenities!

Welcome to a convenient Maui adventure base that is cozy, comfortable and modern! This Premier Vacation Condo in the harbor town known as Maalaea Village and located just 20 minutes from Kahului airport. Island Sands, a resort where you can enjoy a refreshing pool and barbecue grilling while overlooking stunning ocean and mountain viewing. Your tropical paradise includes opportunities to view turtles on a small beach, steps from the condo! This escape truly provides an unforgettable stay!

Superhost

A modern living area features a comfortable sofa and a round coffee table. A wall-mounted TV is positioned across from the seating area. Natural light fills the space, highlighting bamboo flooring. A dining area with wooden chairs is visible, along with a kitchen in the background.

4.81 out of 5 average rating, 106 reviews

Modern 1 Bedroom Suite with Spacious Lanai

Relax in this calm, stylish space in Maalaea. It has everything you need to make this your homebase to explore Maui. Suite features a large private lanai surrounded by tropical plants & trees. New queen bed plus double sofabed. Kitchen with fridge, stovetop, convention microwave and dishwasher. Quiet A/C keeps the suite cool. Located on the 2.5 mile long Sugar Beach. Stroll the beach and enjoy the views across Maalaea Bay. 20 mins from the airport, 13 mins to Kihei, 26 minutes to Lahaina.

4.94 out of 5 average rating, 105 reviews

Oceanfront, Ground Floor Condo Steps to Ocean

The perfect Maui vacation awaits you in this oceanfront ground level condo located on the Kana'i A Nalu property centrally located on the island in Ma'alaea Bay. Watch whales (Dec-Mar) directly from the lanai as they play in the harbor and then fall asleep at night to the waves outside the bedroom window. Discover the longest stretch of beach on Maui - 2.5 miles of secluded white-sand stretching from the condo towards Kihei with views of nearby islands of Kaho'olawe, Molokini and Lanai.

A lanai with a direct ocean view features four wicker chairs and a small ottoman, arranged around a square table. The railing offers an unobstructed sight of the calm waters and distant shores, with sunlight casting soft shadows on the tiled floor.

4.86 out of 5 average rating, 294 reviews

Direct Ocean View!

Direct ocean front view of ocean and harbor. On the 3rd floor with spacious lanai. Beautifully remodeled with tile through out, granite counter tops, full size washer and dryer, custom lighting, walk in shower and AC. There is a queen size Murphy bed in living room. And a full size Murphy bed in bedroom. Walk to shops, restaurants, activities, and Maui Ocean Center. Centrally located with easy access to Kihei, Lahaina and 20 minutes from airport. You can’t get closer to the ocean.

A sunlit balcony features a bar-height table and one chair, overlooking the ocean. The living area includes a comfortable seating arrangement with a lamp and artwork on the walls. The kitchen showcases modern appliances and a neutral color palette, enhancing the inviting space.

4.98 out of 5 average rating, 103 reviews

Oceanfront Panorama: Newly Refreshed 3rd Floor Gem

Welcome to our newly renovated 1b1b 3rd-floor oceanfront condo at Maalaea Banyan, a very popular destination! Steps from the sea, enjoy grand ocean vistas and island breezes. Nestled in Ma'alaea, our harbor town is known for snorkeling cruises and fishing delights. Explore Haycraft Park, Maui Ocean Center, or amble along Sugar Beach. Ideal for whale and turtle sightings. Enjoy a king bed, workspace, living room & bedroom a/c, free parking, pool, & hot tub. Your dream Maui retreat awaits!

A serene outdoor area features well-maintained green grass and several lounge chairs positioned to face the ocean. A table with decorative items is visible in the foreground, while palm trees sway gently in the breeze against a clear blue sky, providing a view of the distant mountains.

4.89 out of 5 average rating, 133 reviews

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!

A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.

4.94 out of 5 average rating, 129 reviews

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.

A modern loft interior features a spacious living area with a light grey sectional sofa adorned with various blue and white throw pillows. A simple wooden dining table with teal seating is visible alongside a kitchen with a white island. Large windows allow natural light, and a decorative wall clock adds charm.

4.98 out of 5 average rating, 178 reviews

Live, Love, Loft in Beautiful Maui

Experience the beautiful island of Maui and all its wonder in this modern loft in Central Kihei. You’re just minutes away from stunning beaches, local markets, and some of the best food on island. Nothing feels like you’ve arrived in Maui like the welcoming sand and warm waters of Charlie Young Beach, just across the street. Head down to The Cove to surf or paddle board with the locals. Or simply relax, put on a classic record and enjoy the sunset from the balcony.

A serene beach scene unfolds with gentle waves lapping at the shoreline. A tall palm tree stands prominently, overlooking the golden sand. Lush greenery frames the foreground, while the distant island can be seen beneath a partly cloudy sky and vibrant blue ocean.

4.85 out of 5 average rating, 111 reviews

$129 Unbeatable Thanksgiving Special

E Komo Mai to our beautiful top of the line condo on the South Shore of Maui. This condo comes loaded and fully stocked with everything you need from your home away from home. Beautiful lanai to sit and have your coffee or afternoon spirits and watch the sunset. Beach towels, chairs, umbrella, cooler & boogie board. Beach (200 steps or less) from your door to capture spectacular sunsets. RB-21667 Holo Imua Properties Hallie Walker

4.9 out of 5 average rating, 234 reviews

Guest suite in Wailuku

Gorgeous 1BR Suite w Outdoor Living

Discover the real Maui at The Blue Door on Church Street, a restored 1930s plantation home in walkable Wailuku Town. Skip the resorts and enjoy a peaceful, stylish one-bedroom villa with a king Nectar bed, private patio, fast WiFi, A/C, and shared infrared sauna—just minutes from ʻĪao Valley, local food, and central to beaches and hikes. @bluedoormaui

Popular amenities for Wailuku family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 164 reviews

☼ Stylish & Bright 2bd Oceanfront Condo | 5★ Views

A bright sleeping area features a spacious bed adorned with quality linens. Beach-themed decor enhances the atmosphere, with a fan overhead and large windows providing views of the private lanai surrounded by lush greenery. A wooden dresser adds functionality to the space.

4.95 out of 5 average rating, 100 reviews

Steps to Beach, Updated Studio + Pools & Hot Tubs

A person stands in the ocean water, silhouetted against a vibrant sunset with shades of orange and gold. Gentle waves lap at the shore, reflecting the warm colors of the sky, while clouds drift above, adding texture to the scene.

4.9 out of 5 average rating, 137 reviews

Incomparable Maui Sunset condo, includes all taxes

4.87 out of 5 average rating, 121 reviews

Lush tropical gardens and palm trees are visible alongside a well-manicured lawn. A blue ocean stretches into the distance under a partly cloudy sky. In the foreground, a swimming pool area features lounge chairs, while a community building can be seen to the left.

Apartment in Lahaina

Condo in Lahaina, New Remodel, Amazingly Peaceful

4.96 out of 5 average rating, 627 reviews

A well-lit studio suite features a comfortable leather sofa and two wooden chairs placed beside a table near a large window. Light drapes filter in through sheer curtains, enhancing the inviting interior, while a decorative piece and soft lamp contribute to a relaxed ambiance.

Apartment in Wailea

Wailea Resort studio suite

A modern kitchen is showcased, featuring wooden cabinetry and a granite countertop. Stainless steel appliances, including a microwave, oven, and refrigerator, are prominently displayed. The kitchen island offers a double sink and is complemented by tile backsplash in calming colors.

4.93 out of 5 average rating, 151 reviews

The Spirit of Aloha-1Bed/1Bath in Tropical Resort

A serene beach scene captures a vibrant sunset reflecting on the water. Signs mark the beach path, and gentle waves lap against the shore. People can be seen at a distance enjoying the sandy beach, framed by lush greenery and a tall tree.

4.82 out of 5 average rating, 108 reviews

Top Floor/Artistic Island Vibes/Premier Location!

4.99 out of 5 average rating, 103 reviews

A spacious lanai offers a stunning ocean view, featuring a glass-top table with two wicker chairs. Bright blue beverages are placed on the table, while blue skies and gentle waves stretch out towards the horizon.

Apartment in Lahaina

Stylish Love Hideaway, Maui Kaanapali Oceanfront

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 117 reviews

The exterior of a spacious home is framed by lush tropical plants and trees. A charming pathway leads to a welcoming front deck illuminated by soft lighting. Large sliding doors enhance visibility into the interior, where comfortable seating is visible in a cozy living space.

Home in Wailea

Mana Hale Vacation Rental

4.97 out of 5 average rating, 129 reviews

The open living area showcases vaulted ceilings and warm wood beams. A modern kitchen island with a marble finish is complemented by stylish pendant lights. A cozy seating area invites relaxation, while large windows offer views of the surrounding landscape, enhancing the bright and airy atmosphere.

Townhouse in Wailea

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

4.85 out of 5 average rating, 125 reviews

The image captures a serene beach scene with clear turquoise waters gently lapping against a sandy shore. Distant islands are visible on the horizon under a bright blue sky adorned with soft white clouds. The tranquil ocean setting suggests opportunities for swimming and snorkeling.

Apartment in Lahaina

A jewel on Oceanfront & Breath Taking Views.

Superhost

A private lanai is showcased with woven seating and a wooden table, offering a view of vibrant green grass that leads to the ocean. Palm trees frame the scene against a clear blue sky, enhancing the relaxing beachside atmosphere.

5 out of 5 average rating, 5 reviews

Breathtaking Location-Sugar Beach #129

4.88 out of 5 average rating, 251 reviews

An inviting bedroom features a spacious bed with a patterned blanket. Two framed paintings adorn the light blue walls, and a bedside lamp provides soft illumination. A doorway leads to a bright living area, with natural light visible from additional outdoor access.

Flat in Wailuku

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

A modern living area features a comfortable sofa and a chair, with a flat-screen TV situated on a wooden media console. Large sliding glass doors provide access to a private lanai, with views of palm trees and the ocean in the background.

4.99 out of 5 average rating, 67 reviews

Oceanfront renovated luxury-best location! SBR 404

4.86 out of 5 average rating, 115 reviews

A comfortable living area features a green sofa with decorative pillows, complemented by a wooden coffee table and matching lamps. A dining space with a table and chairs is visible in the background, alongside a kitchen area with a bright, airy atmosphere enhanced by natural light.

Home in Paia

Two Bedroom Green Turtle House

A sandy path leads from lush greenery to a serene beach. Palm trees sway gently in the foreground, framing views of calm blue waters and distant islands under a clear sky with scattered clouds.

4.97 out of 5 average rating, 33 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 159 reviews

A spacious lanai features a round table with a decorative centerpiece, surrounded by comfortable chairs. Lush palm trees sway gently in the breeze, while the vast ocean and distant shoreline are visible through the railing, under a partly cloudy sky.

Apartment in Maalaea

Turtle Cove Oceanfront Views Island Sands Resort

An open living area showcases a comfortable sofa and a textured area rug. A modern kitchen features stainless steel appliances and a granite countertop, complemented by two barstools. Soft lighting from pendant lamps and a nearby floor lamp enhances the inviting ambiance.

4.99 out of 5 average rating, 191 reviews

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

A cozy living area features a comfortable gray sofa adorned with decorative pillows. A round wooden coffee table with wheels is positioned in front, while natural light streams in through large windows adorned with bamboo shades, revealing a view of tropical surroundings.

4.89 out of 5 average rating, 180 reviews

Island treasure, Ocean Front Maui

The bedroom features a plank headboard with a spacious bed dressed in soothing seafoam colors. Soft accent pillows adorn the bed, including one that reads 'aloha', while a bedside lamp provides gentle illumination.

4.98 out of 5 average rating, 134 reviews

Tropical Kihei Resort | 3 Min Walk to Beach | A/C

A spacious living area features a comfortable grey sofa, complemented by colorful wall art. Large windows allow natural light to fill the room, which includes a dining table surrounded by chairs and a view of the outdoor patio.

4.93 out of 5 average rating, 107 reviews

Oceanfront Home: Steps Away To Beach

A modern living area features a firm couch with decorative cushions and two small wooden side tables. A round coffee table sits in front, arranged on a textured area rug. A decorative floor lamp and potted plant add a touch of greenery to the neutral space.

4.95 out of 5 average rating, 244 reviews

Beach View! MODERN & SPACIOUS! 3 min to Downtown!

A private lanai features a dining table with four chairs, overlooking lush greenery and a sandy beach. Palm trees line the ocean, with distant views of the water under a clear blue sky.

4.98 out of 5 average rating, 127 reviews

Exquisite Oceanfront Remodel - Amazing View!

A serene swimming pool is nestled amidst lush tropical landscaping, surrounded by vibrant greenery and blooming flowers. Sun loungers are positioned near a shaded umbrella, inviting relaxation under the clear blue sky.