Family-friendly holiday rentals in Wailuku

4.95 out of 5 average rating, 246 reviews

Home in Wailuku

The Blue Door on Church Street | Spacious Two Bedr

Enjoy Haleakalā views from this spacious two-bedroom upstairs retreat at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Features include a king Helix bed, queen Helix bed, full-size memory foam sleeper sofa, full kitchen, rainfall shower, AC, fast WiFi, Smart TV, parking for two vehicles, and a large private deck with outdoor dining and lounge seating. Walk to local cafés and restaurants, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui attractions

FamilyKitchenBathroom

4.84 out of 5 average rating, 526 reviews

The outdoor area features a large, inviting pool surrounded by a tiled deck. Comfortable lounge chairs are arranged around the pool, and vibrant potted plants add a touch of greenery. The main house, visible in the background, showcases spacious windows and a welcoming entrance.

Guest suite in Wailuku

Private Poolside Oasis & Ocean Views

Escape to a relaxed tropical retreat in private villa-style suite featuring its own entrance, ensuite bathroom w/ natural stone shower, coffee station, mini fridge, & outdoor bistro seating. Guests also enjoy access to our lush shared pool area and shared kitchen spaces, creating a boutique island experience designed for comfort, connection, and relaxed Maui living. Centrally located & great for exploring all Maui has to offer. Great hikes and beaches nearby! Maui County Permit BBWK 2019/0003

FamilyIndoor spacesPets

Superhost

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

KitchenIndoor spacesParking

4.81 out of 5 average rating, 113 reviews

4.97 out of 5 average rating, 201 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.

FamilyIndoor spacesWalkability

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, 204 reviews

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.

FamilyKitchenAmenities

4.89 out of 5 average rating, 569 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

Indoor spacesKitchenLayout

4.93 out of 5 average rating, 377 reviews

Wake Up in Maui — Walk Out & Start Your Beach Day

Walk to the beach in minutes and enjoy a FREE paddleboard during your stay. This spacious Kihei condo features resort pools, beach gear, and a relaxed Maui vibe—perfect for couples or up to 4 guests 800 sq ft ground-floor condo just steps from the sand. Enjoy a pool, hot tub, and nearby pickleball courts. Watch whales (Dec–Apr) , Digital Nomads & Remote Work: property features premium Fioptics 1 Gig symmetrical internet the Wi-Fi is blazing fast , AC, beach gear, parking, and on-site laundry.

FamilyIndoor spacesBeach

A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.

4.98 out of 5 average rating, 124 reviews

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.

KitchenIndoor spacesCleanliness

4.95 out of 5 average rating, 105 reviews

Apartment in Maalaea

Maalaea Beachfront Resort

Fully renovated 1st level beach front resort steps from the sand. The most centrally located beach front resort on Maui located in peaceful and quiet Maalaea. Wake up and walk miles of uninterrupted, pristine beaches along a national wildlife preserve. The secluded beaches bring peace to anyone looking for a little solitude, and for those looking to have a little fun, you can walk right down the street to Maui's only aquarium, along with a shopping center, funplex, bars and restaurants.

Indoor spacesFamilyCheck-in

4.94 out of 5 average rating, 127 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.

Indoor spacesKitchenWalkability

A scenic view showcases swaying palm trees against a vibrant blue sky, with a glimpse of the ocean in the background. Lush greenery frames a pool area, inviting relaxation, while the buildings provide a residential atmosphere. The beach appears just beyond the manicured lawns.

4.92 out of 5 average rating, 174 reviews

Lovely Oceanfront Condo with pool

Discover Paradise: Lovely Oceanfront Condo with Pool & Unforgettable Views Wake up to the symphony of waves and endless blue horizons in this stunning oceanfront condo, your ideal escape for relaxation, romance, or family adventures. Nestled right on the edge of the beach, this beautifully appointed retreat offers breathtaking panoramic ocean views from your private balcony—perfect for sipping morning coffee as the sun rises over the water or unwinding with a glass of wine at sunset.

KitchenFamilySolo travel

Superhost

A spacious living area is presented, featuring a comfortable seating arrangement with light-colored furniture. Large glass doors illuminate the space and provide views of tropical greenery and the ocean. Wall art depicting serene beach scenes adds a calming touch, enhancing the overall atmosphere.

4.85 out of 5 average rating, 158 reviews

Oceanfront Bliss - Walk to Boats, Bites & Beach!

Welcome to your tropical paradise! Step into our ground floor 1-bedroom, 1-bathroom unit, just steps from the sparkling Pacific Ocean. Surrounded by vibrant Hawaiian plants, enjoy the pool, BBQs, and lush green space. Ideal for families or a romantic getaway, it's a short walk to the stunning 6-mile Sugar Beach. Relax on your lanai and witness Hawaii's longest curl wave, along with mesmerizing sunrises and sunsets. You can spot friendly sea turtles swimming and lounging on the beach!

KitchenIndoor spacesQuiet

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, 199 reviews

Ma'alaea Ocean Front • Whales, Pool & Hot Tub

Indoor spacesFamilyWalkability

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.

4.93 out of 5 average rating, 165 reviews

Oceanfront Getaway, Brand New, Steps To Beach

KitchenFamilyBeach

A lanai offers a scenic view of the ocean, framed by palm trees swaying in the breeze. A round dining table with four chairs is set on the patio, surrounded by manicured greenery, while the glistening water is visible in the distance.

4.81 out of 5 average rating, 172 reviews

Ocean front! Listen to the waves all day and night

KitchenIndoor spacesAccuracy

A serene beach scene is captured at sunset, with canoes resting on sandy terrain. The sky displays soft hues of orange and yellow, reflecting over the water. A sign stands nearby, providing information about the area, framed by gentle foliage and distant clouds.

4.91 out of 5 average rating, 166 reviews

Beautiful Studio Condo with Partial Ocean View

Indoor spacesKitchenHiking

A clear view of a swimming pool is presented, surrounded by lounge chairs and tropical greenery. Palm trees frame the scene, with the ocean visible in the background under a bright blue sky dotted with clouds.

4.92 out of 5 average rating, 194 reviews

3BR spacious Condo with Ocean View in top location

KitchenIndoor spacesTV

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, 159 reviews

Oceanfront Condo with Pool and Jacuzzi

FamilyIndoor spacesPool

4.99 out of 5 average rating, 150 reviews

A sandy beach stretches along the coastline, framed by tall palm trees swaying gently. Gentle waves lap against the shore, creating a serene atmosphere. In the distance, lush green hills rise under a partly cloudy blue sky, enhancing the natural beauty of the location.

Condo in Wailea

Very Comfortable Kamaole Sands Condo Sleeps 4

Indoor spacesFamilyGetting around

4.99 out of 5 average rating, 139 reviews

A spacious living area features a light grey sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, accompanied by a textured area rug. A piece of wall art depicting a boat on water is displayed above the sofa, complemented by a floor lamp and a plant on a side table.

Condo in Wailea

Spacious garden oasis next to Maui's best beaches!

Indoor spacesFamilyView

Family- and pet-friendly home rentals

Farm stay in Haiku-Pauwela

The exterior of a private cabin is surrounded by lush greenery, featuring vibrant tropical plants. A porch with rocking chairs offers a welcoming spot to relax. The cabin's distinctive architecture includes a sloping roof and decorative wooden details, providing a harmonious blend with the natural environment.

Ocean View - Private Cabin

FamilyIndoor spacesHospitality

4.97 out of 5 average rating, 332 reviews

4.93 out of 5 average rating, 420 reviews

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

Kula Jewel - Pool, Hot Tub & Awesome Views!

FamilyKitchenParks

A bright living area is showcased with large glass doors offering access to an outdoor space. Comfortable seating is provided by a gray sofa and wicker chairs, accented with blue and patterned cushions. A glass coffee table is placed centrally, complemented by a mounted flat-screen TV.

4.86 out of 5 average rating, 107 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

Indoor spacesKitchenBeach

A serene beach scene at sunset showcases soft hues of orange, pink, and purple in the sky. Silhouetted figures walk along the shoreline, while a tall palm tree stands nearby, framing the tranquil landscape and creating a sense of calm.

4.84 out of 5 average rating, 431 reviews

Ocean View Superior Deluxe - 200

KitchenFamilyCondition

4.92 out of 5 average rating, 146 reviews

A cozy outdoor deck is showcased, featuring two wicker chairs and a small table, inviting relaxation. The inviting turquoise door stands adjacent to a wall with the word 'Aloha' elegantly displayed. String lights add a warm touch above, surrounded by tropical greenery.

Home in Kihei

Enjoy paradise living at the THERE Maui House!

FamilyIndoor spacesTV

4.87 out of 5 average rating, 120 reviews

Home in Paia

Two Bedroom Green turtle House

KitchenFamilyDecor

4.97 out of 5 average rating, 145 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

Indoor spacesFamilyBiking

A private lanai features a round glass-top table surrounded by colorful cushioned chairs. Lush tropical plants and palm trees create a serene garden view, while a clear blue sky adds brightness to the scene.

4.95 out of 5 average rating, 114 reviews

Walk to Kam Beach! King Bed, Pools, Pet Friendly.

FamilyKitchenParking

Family-friendly home rentals with a pool

A serene outdoor seating area features a small round table and two chairs, overlooking the ocean with distant mountains under a clear blue sky. Nearby, a cozy indoor space showcases a soft couch adorned with decorative throws, complemented by a light wooden accent table with greenery.

4.96 out of 5 average rating, 125 reviews

Oceanfront Spectacular Condo

FamilyIndoor spacesValue

A bright living area features a turquoise accent wall and large windows, offering views of the ocean. A light-colored sofa is paired with a glass coffee table and rattan chairs around a dining table. Natural light enhances the inviting space, complemented by beach-themed decor.

4.86 out of 5 average rating, 138 reviews

Oceanfront Bliss Pool & Stunning Views Hono Kai C3

KitchenIndoor spacesParks

Superhost

A serene view of the ocean is captured from the lanai, framed by the silhouettes of palm trees. An outdoor table and chairs are positioned for relaxation, with a glimpse of a pool area and lush greenery below.

4.83 out of 5 average rating, 328 reviews

Hello View!

Indoor spacesFamilyAmenities

A spacious living area features a large window overlooking the ocean, with a green lawn and lounge chairs visible outdoors. A round dining table and four wooden chairs are positioned adjacent to a sleek console. Natural light creates a bright and open atmosphere.

4.85 out of 5 average rating, 140 reviews

OCEANFRONT Hono Kai / TA-081-709-8752-01

Indoor spacesFamilyGetting around

A comfortable living area features a large flat-screen TV on a wooden media console. Sliding glass doors provide access to the private lanai, showcasing ocean views. A ceiling fan above adds to the airy ambiance, with a cozy coffee table positioned in front of the seating area.

4.98 out of 5 average rating, 120 reviews

Stunning Oceanfront 1bd - Maalaea Kai 315

KitchenIndoor spacesWi-Fi

A private beachfront lawn is shown, featuring several lounge chairs arranged on lush green grass. Umbrellas stand nearby, providing shade. A backdrop of palm trees frames the view of the ocean, with gentle waves lapping against the shore under a partly cloudy sky.

4.93 out of 5 average rating, 220 reviews

Oceanfront Condo on magic Sugar Beach - Ocean View

KitchenIndoor spacesAir conditioning

A stunning sunset casts vibrant colors across the sky above the ocean. Silhouetted palm trees frame the scene, while distant mountains provide a scenic backdrop. The calm water reflects the hues of pink, orange, and purple, creating a serene atmosphere.

4.96 out of 5 average rating, 129 reviews

2BR 2Bath - Oceanfront Remodeled Condo!

FamilyIndoor spacesCondition

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.