Family-friendly holiday rentals in Kahului

4.98 out of 5 average rating, 249 reviews

A group of alpacas, varying in color and patterns, stands along a fence in a lush green pasture. Their calm expressions reflect the peaceful environment, with rolling hills and trees visible in the background, creating a serene rural setting.

Guest house in Kula

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

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.

4.87 out of 5 average rating, 257 reviews

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!

4.89 out of 5 average rating, 547 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

4.95 out of 5 average rating, 440 reviews

A vibrant sunset casts colorful hues across the sky, with layers of pink, orange, and blue blending seamlessly. The foreground features green land and trees. In the background, a cottage rests against the horizon, overlooking a serene coastal landscape.

Cottage in Kula

Oceanview Cottage away from heat! w/ County Permit

Closest Airbnb to Haleakala National Park & Road To Hana. Away from 100 degree heat & traffic & yet still close to food & market! Private Cottage on 2acres of orchard on Haleakala, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Two master suites with ensuite Full Baths. For past guests whom love this home, this AirBnB ends on 12/31/26. Hawaii Supreme Court ruled no more short term rental in agriculture lands.

4.93 out of 5 average rating, 398 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!

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!"

4.96 out of 5 average rating, 181 reviews

A lush outdoor garden area is visible, featuring vibrant green grass and tropical plants. A seating arrangement with a table and chairs can be seen under an overhang, framed by a flowering tree. The ocean glistens in the distance beneath a clear blue sky.

Townhouse in Lahaina

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

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.

4.98 out of 5 average rating, 323 reviews

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.

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.

4.93 out of 5 average rating, 671 reviews

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

An open concept living space is displayed, featuring a comfortable leather sofa and a wooden dining table. Large sliding glass doors invite natural light, while a modern kitchen is visible in the background. Ceiling fans and decorative elements enhance the airy ambiance.

4.94 out of 5 average rating, 438 reviews

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.

4.92 out of 5 average rating, 277 reviews

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.

The studio features two spacious beds with gray bedding, positioned beside a kitchenette that includes a mini-fridge and cabinetry. A wooden artwork hangs on the wall, while natural light filters through the window covered by light gray curtains.

4.88 out of 5 average rating, 185 reviews

Maui Private Ground Floor Studio mins from Airport

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.

4.94 out of 5 average rating, 104 reviews

A bright bedroom features a spacious bed adorned with white linens and green accents. Large windows provide natural light and views of the surrounding greenery. A small table with two chairs is positioned nearby, complemented by soft drapes that frame the windows.

Guest house in Makawao

Serene Starting Point for Roaming Island Wide

The Orchid Wing is a private 2-bedroom guest wing within our intimate historic inn, ideal for families or close friends ready to reconnect and roam. Vintage charm, views of Maui’s largest Norfolk pine, lush gardens, beach gear, Haleakalā blankets, and daily brekky baskets create a warm Upcountry home base for island adventures. No indoor common area. Please see floor plan in photo gallery. BBMPT20200001

Popular amenities for Kahului family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 151 reviews

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.

Guest house in Haiku

Maile Bungalow- County Licensed

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, 151 reviews

Oceanfront Getaway, Brand New, Steps To Beach

An open-concept living area is featured with a light-filled atmosphere. A comfortable sofa faces a sleek black entertainment unit with a large screen TV. The kitchen area is visible, equipped with modern appliances and a breakfast bar with three stools. Artwork depicting the ocean is displayed prominently above the kitchen.

4.96 out of 5 average rating, 141 reviews

🌈Your Hawaiian Happy Place 🌺Steps from the Beach🏝

4.88 out of 5 average rating, 236 reviews

Breathtaking, FRONT ROW seat to the azure Pacific

Apartment in Wailea-Makena

A bright sleeping area features a spacious bed dressed in crisp white linens. Flanking the bed are two nightstands with lamps. A smart TV is mounted on the wall opposite, and large windows with white shutters allow natural light to enter the room.

4.98 out of 5 average rating, 463 reviews

Boathouse Studio Condo in Wailea, Hawaii

A spacious kitchen area features a dark countertop with a cooking surface, complemented by modern stainless steel appliances. A dining space with a wooden table for four is visible, alongside stylish artwork. Natural light fills the room through a nearby window.

4.94 out of 5 average rating, 131 reviews

Stylish Oceanfront Ground Floor 1BR

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.

4.9 out of 5 average rating, 149 reviews

Oceanfront Condo with Pool and Jacuzzi

4.98 out of 5 average rating, 150 reviews

Tropical Retreat • King • Beach • Pool/Hot Tub

Family- and pet-friendly home rentals

5 out of 5 average rating, 47 reviews

Guest house in Kihei

Sunflower Suite

The exterior of a two-story home is surrounded by lush tropical landscaping. Vibrant red and green foliage adorns the front yard, while a covered porch provides shaded seating. The building features large windows allowing natural light, with a backdrop of blue skies and scattered clouds.

4.97 out of 5 average rating, 63 reviews

Ho’oko’ana Maui Farm Stay. On Staycation TV

5 out of 5 average rating, 3 reviews

Flat in Lahaina

Pool, Hot Tub, Beach, West Maui Mountain View

4.89 out of 5 average rating, 71 reviews

A covered balcony features a round mosaic table surrounded by black mesh chairs. Lush greenery is visible in the foreground, with trees framing the view of distant mountains against a clear sky.

Home in Makawao

Pookela Paradise-Newly Renovated, Fantastic Views!

A comfortable bedroom features a spacious bed with a patterned decorative pillow. Two bedside lamps provide soft lighting, while a piece of wall art showcases palm leaves. A dresser and a white accent chair are positioned in the room, enhancing the relaxed atmosphere.

4.84 out of 5 average rating, 284 reviews

Cozy Cute Condo | Maui Vista | Walk to The Beach

5 out of 5 average rating, 5 reviews

Home in Kihei

NEW! 1 bed | Walk to town/beach (S. Kihei)

4.86 out of 5 average rating, 100 reviews

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.

Flat in Kihei

Kamaole Ocean View 7bd 3bth Beach Full AC HOT TUB

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.

4.93 out of 5 average rating, 74 reviews

Oceanfront renovated luxury-best location! SBR 404

Family-friendly home rentals with a pool

A spacious living area features a large flat-screen TV and a dark brown couch. Open sliding doors reveal a beautiful lanai with a dining table and umbrella, overlooking the ocean and providing panoramic views of the water and distant islands.

4.97 out of 5 average rating, 116 reviews

Dolphin Penthouse at Milowai

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.

4.97 out of 5 average rating, 190 reviews

Live, Love, Loft in Beautiful Maui

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, 201 reviews

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

The oceanfront view captures gentle waves rolling onto a sandy beach, with vibrant shades of turquoise blending into deeper blue hues. A coastal landscape in the background features distant hills under a canvas of partly cloudy skies.

4.99 out of 5 average rating, 142 reviews

Beach/Oceanfront Property, Sleeps 5, Kihei Maui

5 out of 5 average rating, 186 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

4.99 out of 5 average rating, 217 reviews

A charming bungalow is surrounded by lush greenery and tropical landscaping, with tall palm trees framing the entrance. A dark blue SUV is parked in the driveway, positioned beside the front door. Bright sunlight highlights the vibrant plants and landscaping, creating a welcoming atmosphere.

Bungalow in Lahaina

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

4.95 out of 5 average rating, 153 reviews

Apartment in Lahaina

Kaanapali Fairway Vista - Legal STR Hotel Zoned

An aerial view captures the coastal Menehune Shores complex, showcasing its resort-style architecture alongside the ocean. Lush green lawns extend towards the shore where gentle waves lap against the sandy beach. The backdrop features the expansive landscape of Maui, highlighting both land and sea.