Family-friendly holiday rentals in Haiku-Pauwela

Apartment in Haiku-Pauwela

A bright and inviting interior space features a small dining area with two tall chairs and a table beside a large window, allowing natural light to fill the room. A kitchenette is visible in the background, along with decorative plants and a guitar displayed on the wall.

Ho'okipa Hideaway - Walk to Restaurant/Store

Ho’okipa Hideaway is the ideal home base for all of your Maui adventures. This private studio includes a modern kitchenette, newly remodeled bathroom, and a screened-in lana’i (The Zen Den). It offers its own gated, private entrance, a large, private, tropical garden, and a designated parking spot. Walk to "Baked on Maui" for breakfast and lunch, a little market, and several local surf shops. We have been licensed by the County of Maui for 11 years and maintained a 4.9-5.0 rating on Airbnb.

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4.91 out of 5 average rating, 386 reviews

4.97 out of 5 average rating, 295 reviews

Home in Haiku-Pauwela

Live Like a Local; near Coffee, Road to Hana and Haleakala

Grab a coffee and drive to the beach to catch waves or watch sea turtles nesting in the sand. This peaceful home with a private yard, outdoor shower, and fun surfboard fence is a great base for exploring the Road to Hana or Haleakala. Located on the quiet north shore of maui, 1 hour from popular tourist areas. Ideal for returning maui visitors who want to stay on the north shore or guests splitting their stay between 2 sides of the island of Maui. Sleeps: 4 guests max (including kids/infants)

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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

NOTE: Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. Located on a working coffee plantation and food forest, this restored cabin is private but close to lots of upcountry activities. Kitchen, ocean view, open concept, great lanai spaces, plenty of off-street parking, access to private hiking trails.

Indoor spacesFamilyRiver

4.97 out of 5 average rating, 332 reviews

Farm stay in Haiku-Pauwela

A charming studio cottage with a distinctive shingle exterior is set among lush greenery. A golden retriever rests on the pathway in front, alongside large trees that provide shade. A vibrant green door invites guests into the cozy interior.

Adorable Gingerbread House Farm Stay, Makawao

This LEGALLY PERMITTED Farm Stay has the lush beauty and privacy,, without the drive to Hana! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. Seasonal stream in the back yard. Simply BEAUTIFUL! We gave 8.5 acres of diversified farm-fruit, water lilies, 10,000 sq ft greenhouse) Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

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4.94 out of 5 average rating, 685 reviews

4.9 out of 5 average rating, 173 reviews

The exterior view shows a charming gray house with white trim and multiple windows. Flower boxes are mounted under the windows, and a concrete pathway leads past the property. Lush greenery and tall trees are visible in the background under a clear blue sky.

Home in Haiku-Pauwela

Quaint 4-bedroom in Ha'iku, Maui

Bring the whole family to the north shore of Maui and stay in our quaint, plantation-era home! At Kihau Gardens (Maui County STRH Permit #2019/0001 and Hawai'i State TAT #T-036-968-8576) we offer a unique home. On each side of a carport, there are two bedrooms, a living area, a small office space, and one and a half baths. Our home in Ha'iku is the perfect stay for two small families who want to explore the north shore, upcountry, Haleakala crater, and the epic drive to Hana.

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Guesthouse in Haiku-Pauwela

A sprawling tree takes center stage against a backdrop of lush greenery and a blue sky dotted with clouds. Soft sunlight filters through the leaves, creating gentle patterns of light and shadow across the manicured grass of the expansive landscape.

Peaceful • Haiku Retreat • Beach 10 & Paia 15 Min

Escape to a spacious studio at Mana Aina, our peaceful 12-acre organic hobby fruit farm in beautiful Haiku, Maui. Enjoy privacy and open space, just 10 minutes from Maui's North Shore beaches. Stroll through tropical gardens, admire the fruit trees, and experience the peaceful charm of Upcountry Maui. Restaurants, beaches, waterfalls, hiking, and the Road to Hana are all nearby, making Mana Aina an ideal base for exploring the island before returning to relax each evening.

FamilyKitchenCleanliness

4.88 out of 5 average rating, 146 reviews

Farm stay in Haiku-Pauwela

Malie at Haiku Garden Cottages Farm Sanctuary

Welcome to Haiku Garden Cottages, a licensed Farmstay and BnB on Maui’s North Shore (Permit BBPH2017/0002). Mālie is a charming cottage where you can sip coffee on the screened-in lanai, wander tropical gardens, and settle into island rhythms. Enjoy ocean and garden views, a private outdoor shower, and peaceful indoor-outdoor living—just minutes from Haleakalā, the Road to Hāna, nearby beaches, hiking trails, local restaurants, and farmers markets.

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4.94 out of 5 average rating, 542 reviews

4.96 out of 5 average rating, 105 reviews

An open-concept kitchen features modern appliances and a central island with a sink, surrounded by wooden chairs. Sunlight floods the room through large sliding glass doors that lead to a deck with seating, showcasing views of greenery and distant mountains.

Cottage in Haiku-Pauwela

Haiku Hideaway - Stand-alone 2 bedroom farm house

Our country farmhouse has a very unique feel with detailed craftsmanship (built by the owner). It’s a 2/1, 1000sqft open concept with a 500 sq. ft. covered deck off the living room and views of the ocean & mountains. We have goats and plenty of trees . We are 6mi to Hoʻokipa Beach Park, 10 min from Twin Falls, 6mi to Makawao & 9mi to Pāʻia. Quiet neighborhood and private. Come relax! TA-122-773-8112-01. GE-122-773-8112-01 BBPH 2021/0001

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4.83 out of 5 average rating, 219 reviews

A distinguished bamboo cottage is elevated on stilts, surrounded by lush tropical vegetation. Wooden decks wrap around the structure, providing access to outdoor seating areas. Large windows offer views of the surrounding greenery, harmonizing the indoor and outdoor environment.

Cottage in Haiku-Pauwela

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

Welcome to your "Hawaiian Dream Temple" [PERMIT- BBPH2012-0004] [TMK (2) 2-7-029: 015-0000] Our tropical bamboo 2 bedroom - 1 bathroom temple is a private house that invites you to true Maui. We are in a quiet area in upcountry, Haiku away from the hotels. You can experience the little sanctuary and hidden paradise that still exists, close to Hana and Haleakala crater. It is surrounded by tall trees, tropical flowers and lush vegetation.

FamilyIndoor spacesHiking

4.99 out of 5 average rating, 218 reviews

An outdoor dining area features a wooden table surrounded by six cushioned chairs. Lush greenery and palm trees frame the view, while the distant ocean is visible under a clear sky, creating a serene space for al fresco meals.

Cottage in Haiku-Pauwela

North Shore Ocean View Cottage

This recently built comfortable cottage is located on the north shore of the island of Maui, tucked away in the quiet countryside of Haiku but relatively close to major attractions! Enjoy a relaxing vacation in a rich tropical setting with spectacular ocean views! Please Note: State of Hawaii Maui County adds 17.96% tax to your guest fees. TA-060-126-6176-01 GE-060-126-6176-01 BBPH 2016/0001 SUP 2 2015/0008

FamilyIndoor spacesAmenities

4.92 out of 5 average rating, 103 reviews

The exterior of a two-story home is displayed amid lush greenery. A spacious deck is highlighted with white railings and a pergola, complementing the tranquil surroundings. The sky is bright with scattered clouds, enhancing the feeling of openness and serenity.

Home in Haiku-Pauwela

The Art Estate, Haiku Maui Hawaii

Our spacious, open-floor-plan home has a contemporary style. The secluded 17-acre, lush, tropical estate has exotic varieties of Bamboo, Palms, Avocados, and various fruit trees. Located on the grounds is a private, functioning, award-winning art studio creating films, photography, video installations, and sculpture. If you are looking to explore, we are just a quick ten-minute drive to the best beaches on the North Shore!

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Guesthouse in Haiku-Pauwela

A charming cottage is set on a spacious lawn, surrounded by lush greenery. The exterior features a broad lanai with white railings, providing a welcoming entrance. Tropical trees and plants frame the property, contributing to a serene atmosphere.

Maile Bungalow- County Licensed

Maui County License: BBPH2009/0012 (taxes included in rate) Lovely cottage with ocean and country views, surrounded by tropical flowers and fruit trees located in a small quiet and peaceful neighborhood in Ha'iku. The cottage is off the road and the neighborhood has no through traffic. Walking distance (15min) to Ha'iku's Market Place and bus stop. The cottage is well equipped with all amenities you need to feel home.

FamilyIndoor spacesGetting around

4.93 out of 5 average rating, 152 reviews

Popular amenities for Haiku-Pauwela family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

KitchenFamilyQuiet

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

KitchenFamilyWalkability

4.94 out of 5 average rating, 147 reviews

Condo in Lahaina

Beachfront Resort, Peaceful Mountain View Studio

Indoor spacesKitchenHiking

4.89 out of 5 average rating, 282 reviews

Across Beach! Ground Floor 2 bed 2 bath, sleeps 6

KitchenIndoor spacesCleanliness

4.89 out of 5 average rating, 212 reviews

Apartment in Kihei

Family-friendly Oceanview beach retreat | AC, Pool

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An aerial view of the Maui Sunset beachfront complex reveals manicured lawns and vibrant tropical landscaping. A central pool is surrounded by palm trees, with direct beach access visible in the background. Tennis courts are located adjacent to the lush green area.

4.9 out of 5 average rating, 105 reviews

Spacious 2BR + Private Alcove @ Maui Sunset, AC

Indoor spacesFamilyShared spaces

A large swimming pool is surrounded by lounge chairs and tropical landscaping, offering views of palm trees and the ocean. The area features a sun deck, umbrellas, and a shaded seating spot, contributing to a relaxed resort environment.

4.92 out of 5 average rating, 170 reviews

Spacious comfy unit Netflix & huge pool Maui Hill

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Condo in Napili-Honokowai

Oceanfront Condo at Napili Bay | Newly Refreshed

FamilyIndoor spacesHiking

4.91 out of 5 average rating, 169 reviews

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 120 reviews

Home in Paia

Two Bedroom Green turtle House

KitchenIndoor spacesAccuracy

4.94 out of 5 average rating, 380 reviews

A vibrant rainbow arcs across the sky, framed by tall palm trees. Lush greenery and distant trees fill the background, enhancing the natural beauty of the surroundings. The scene conveys a sense of tranquility and connection to nature.

Farm stay in Hana

JJ’s Hāna Hale - Farm Style Cottage STHA2021/0001

FamilyIndoor spacesQuiet

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!

Indoor spacesKitchenParking

4.95 out of 5 average rating, 128 reviews

A hammock is suspended between palm trees, overlooking the ocean. The blue sky is dotted with clouds, while the grassy area invites relaxation. The view captures the tranquil water and lush greenery, creating a serene setting for leisure.

Home in Hana

Hana Maui Luxury Elua Cottage

FamilyKitchenPets

4.96 out of 5 average rating, 232 reviews

Cottage in Maui County

Haleakala Cottage - private hot tub, pool access

KitchenFamilyWalkability

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

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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

Indoor spacesFamilyCheckout

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

KitchenIndoor spacesBarbecue

Family-friendly home rentals with a pool

A vintage toy van is positioned on a sandy beach, facing a vibrant sunset over the ocean. Warm golden light reflects off the waves, creating a serene scene. The gentle surf adds a sense of calm to the atmosphere, with small ripples lapping at the shore.

4.93 out of 5 average rating, 205 reviews

Groovy bright condo 2 bed / 2 bath South Kihei

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 124 reviews

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.

Condo in Maalaea

Coastal Dream Oceanfront Condo!

Indoor spacesFamilyCleanliness

A spacious lanai features a glass-top dining table surrounded by six metal chairs. Framed by two palm trees, panoramic views of the ocean and distant mountains are visible. The scene captures the tranquil beauty of the outdoor space with clear blue skies and gentle waves.

4.88 out of 5 average rating, 145 reviews

3BD Oceanfront Views I Menehune Shores 414

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Holiday home in Napili-Honokowai

The living area showcases large floor-to-ceiling windows framing ocean views. A comfortable sectional sofa is positioned around a wooden coffee table, with a wall-mounted TV and a rustic cabinet nearby. A ceiling fan adds a cooling touch, and outdoor seating is visible through the glass doors.

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt

FamilyIndoor spacesCheck-in

4.97 out of 5 average rating, 135 reviews

4.94 out of 5 average rating, 127 reviews

Condo in Maalaea

Oceanfront, Ground Floor Condo Steps to Ocean

Indoor spacesFamilyWi-Fi

Apartment in Napili-Honokowai

A spacious balcony features a simple dining table surrounded by two chairs, offering an unobstructed view of the ocean. Palm trees frame the scene, while a bottle and glass sit on the table, reflecting the bright blue sky above and the serene water below.

Maui Full Oceanfront Paradise

KitchenFamilyAccess

4.97 out of 5 average rating, 105 reviews

A bright living area offers ocean views through expansive sliding glass doors. Comfortable chairs are positioned towards the balcony, where coastal scenery includes palm trees swaying in the breeze. Neutral decor is accented with beach-themed cushions, and a TV set is present on a stylish console.

4.99 out of 5 average rating, 232 reviews

Mana Kai 608: Oceanfront Remod- Thanksgiving OPEN!

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A picturesque view captures a beach at sunset with vibrant orange and purple hues in the sky. Swaying palm trees line the shoreline, where beachgoers can be seen enjoying the golden sand and gently lapping waves. The grassy area near the beach is dotted with lounge chairs.