Family-friendly holiday rentals in Waihee-Waiehu

4.98 out of 5 average rating, 232 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.

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

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, 509 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

4.98 out of 5 average rating, 140 reviews

An inviting kitchen area features modern cabinetry and a spacious island with three stools. Stainless steel appliances are complemented by elegant light fixtures, and natural light brightens the room through a nearby window.

Apartment in Wailuku

Makani A Kai A7 modern beachfront, pool, a/c, w/d

Halerentals MAK A7 is a romantic, brand new beachfront condo with huge patio, lawn, and incredible views of the beach, bay, & Haleakala volcano-- centrally located for day trips around the island, and off the beaten tourist path. Cool a/c in every room -- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 2bed/2bath condo- w/ fully stocked kitchen & beach gear. Ideal for swimming, paddle boarding, snorkeling, and surfing-- amazing value for families and couples.

4.92 out of 5 average rating, 1,135 reviews

A bright bedroom features a queen bed with a navy blue coverlet, complemented by a decorative yellow pillow. Light streams in through the window, highlighting a wooden chest at the foot of the bed and a bedside table. A comfortable chair and a foldable stool add functionality to the space.

Flat in Kula

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

4.98 out of 5 average rating, 390 reviews

A collection of colorful canoes is positioned along the shore, framed by swaying palm trees. The ocean waves glisten under a moody sky, transitioning to sunset hues, while soft clouds add texture to the backdrop.

Guest suite in Kihei

"Dancing Turtle's "Guest Suite"

CHECK-IN WINDOW IS: 3-8PM. GIVE US AN HOUR WINDOW FOR CHECK-IN TIME AT LEAST 1 DAY BEFORE ARRIVAL; we need to adjust our schedule to make sure we can welcome you. We will try to accommodate your arrival time (e.g. later flight) as much as possible. NO EARLY CHECK IN or BAG DROP OFF. You will be in our private. Guest Apt. with fully equipped kitchen. We live upstairs. We are a licensed "B&B" , which is the Maui County destination to operate legally in an “owner occupied residence”.

4.84 out of 5 average rating, 160 reviews

An inviting entrance is framed by lush greenery, featuring a stone pathway that leads to a swimming pool area. Strong wood beams support a structure adorned with lamps, while vibrant palms and decorative rocks enhance the natural ambiance.

Place to stay in Wailuku

Stall #4 Safe place to sleep in your vehicle

Discover the perfect haven for budget travelers looking for a secure and comfortable place to rest! Our offering is ideal for those parking and sleeping in their cars or RV rentals, and it comes without the extra cost of a room. Enjoy the convenience of an outhouse and hot showers available during business hours, ensuring you feel refreshed and rejuvenated. Experience peace of mind with our fully fenced yard, designed for your privacy and security.

4.93 out of 5 average rating, 475 reviews

The living area features a wooden dining table surrounded by four chairs, with a comfortable beige sofa positioned nearby. Large glass doors provide natural light and views of the backyard, framed by vibrant greenery. A flat-screen TV is mounted on the wall opposite.

Apartment in Paia

Locally-Owned Eco-Friendly Condo on Road to Hāna

Kūʻau on Maui's north shore offers uncrowded access to unique beaches and the best proximity to Mama's Fish House, Pāʻia town, Road to Hāna, Haleakalā National Park, and Kahului airport. Designed with environmentalist principles, every detail has been mindfully chosen. This local family-owned small business proudly supports other local businesses. I welcome people of all backgrounds to connect with the natural environment and cultures of Maui.

4.91 out of 5 average rating, 258 reviews

Flat in Wailuku

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.

4.87 out of 5 average rating, 123 reviews

The modern studio features two spacious beds, a wooden nightstand, and a wall-mounted TV. A desk and chair occupy one corner, while large windows offer natural light and views of the surroundings. Light-colored flooring enhances the bright and open atmosphere.

Flat in Wailuku

Unit 10 Waena Inn - 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.

4.89 out of 5 average rating, 164 reviews

The exterior of a charming home is highlighted, featuring a distinctive turret and surrounded by lush greenery. Palm trees and flowering plants add to the tropical ambiance. The welcoming porch is framed by columns, inviting guests to enjoy the natural surroundings.

Home in Paia

Villa Parthenope in Paia bnb #3 *****

Permit n. : BBPH (PHONE NUMBER HIDDEN) (for the permit nuber look at the pics) Prices are inclusive of taxes. Lovely and Romantic home with private bath in Paia, about 7/8 min. walking distance from the beaches and all the services in town.Private entrance. Kitchen corner with hot plates, coffee machine, mini oven, microwave,fridge, blender, and all that you need to cook at home. We DON’T accept kids to this property.

4.93 out of 5 average rating, 235 reviews

A sunset is framed by tall pine trees, casting long shadows against the grassy landscape. The warm orange and yellow hues of the sun blend with soft pastel tones in the sky, indicating the day's end and offering a serene backdrop to the natural setting.

Apartment in Molokai

Welcome to Hotel Molokai, Unit 102...

*This unit is located on the island of Moloka'i, not MAUI. Welcome to Moloka'i, where time slows down and you're able to relax and unwind. Hotel Moloka'i is a hotel convenient located on the outskirts of Kaunakakai town. Whether you're on Moloka'i for business or pleasure, our unit offers you a comfortable place to stay. Enjoy beaches all to yourself, go on hikes and listen to live music at Hiro's 'Ohana Grill.

Popular amenities for Waihee-Waiehu family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The image captures a serene view of a landscaped garden area with a central swimming pool. Surrounding palm trees provide shade, and sun loungers are arranged around the pool. The ocean is visible in the background, framed by a clear sky and gentle hills.

4.93 out of 5 average rating, 347 reviews

Oceanfront Kihei Condo Free SUP & Resort Pools!

A spacious living area is furnished with a large, comfortable blue sofa and patterned accent pillows. A round, woven coffee table sits at the center on a textured area rug. A ceiling fan rotates above, and a large wall art piece complements the modern decor.

4.95 out of 5 average rating, 239 reviews

WalkTo The Ocean! Swim With The Turtles and Relax!

4.95 out of 5 average rating, 131 reviews

An open-concept living area features a spacious dining table with blue upholstered chairs, complemented by a calming color palette. The kitchen, equipped with modern appliances, is visible in the background, while natural light fills the space through large windows.

Apartment in Wailea

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

A sandy beach stretches along the coastline, leading to a distant rocky outcrop separating the water from the shore. A multi-level building stands nearby, surrounded by greenery, with gentle waves lapping at the beach under a clear blue sky.

4.82 out of 5 average rating, 187 reviews

Charming Maui Beach Condo Steps from the Shore!

4.96 out of 5 average rating, 626 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 dining table is set with plates and utensils, positioned on a lush green lawn. Palm trees surround the area, offering a tropical ambiance with the ocean visible in the background under a partly cloudy sky.

4.92 out of 5 average rating, 132 reviews

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

A scenic view reveals the ocean with soft waves meeting sandy shores, framed by palm trees. In the foreground, tennis courts are visible against a backdrop of rolling hills, showcasing lush greenery under a clear blue sky.

4.98 out of 5 average rating, 105 reviews

Maui is Open - Come Support the Locals

4.94 out of 5 average rating, 170 reviews

An outdoor dining table is set for four, featuring plates and cutlery, with a backdrop of lush greenery and panoramic ocean views. Palm trees frame the scene, and the sky displays soft hues of sunrise or sunset, enhancing the tranquil atmosphere.

Apartment in Wailuku

Boho Beach Retreat *OCEAN VIEWS*

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 116 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

4.99 out of 5 average rating, 351 reviews

The cottage exterior is framed by lush greenery and vibrant flowers, complemented by a decorative stone pathway leading to the entrance. A unique circular window and a red door enhance the cottage's character, while balconies offer inviting views of the surrounding landscape.

Farm stay in Haiku

Maliko Retreat

4.96 out of 5 average rating, 108 reviews

An open living area features a comfortable red leather sofa with decorative pillows. A dining table with wooden chairs is set nearby, and a well-equipped kitchen can be seen in the background. Natural light illuminates the space, enhancing its welcoming ambiance.

Home in Lanai

The Artists House

A cozy studio condo includes two double beds covered with white bedding and a blue accent thrown. Large glass doors lead to a private patio, offering natural light. A small seating area and a TV are visible, adding to the comfort of the space.

4.85 out of 5 average rating, 129 reviews

Updated 2-Bed Studio- Steps to Beach/Shops/Dining

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.

4.85 out of 5 average rating, 125 reviews

A jewel on Oceanfront & Breath Taking Views.

4.94 out of 5 average rating, 335 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

4.91 out of 5 average rating, 216 reviews

An aerial view of the Hana Homestead showcases its spacious grounds and the two-story structure. Surrounding greenery and trees enhance the property, while the exterior displays a blend of modern and rustic design elements. Nearby homes and roads are visible in the background.

Home in Hana

Hana Homestead by the Beach

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

Family-friendly home rentals with a pool

A spacious lawn area features several lounge chairs and tables, surrounded by palm trees. Red umbrellas provide shade over some seating, while the ocean is visible in the background. The shoreline is framed by gentle waves under a bright blue sky.

4.87 out of 5 average rating, 426 reviews

Can be 2 Units! Modern On Beach Ocean View Balcony

A serene outdoor view of lush greenery and ocean in the distance is presented. In the foreground, a white coffee cup rests next to an open book, while colorful flowers add a touch of warmth to the setting.

4.85 out of 5 average rating, 295 reviews

Romantic Maui Gateway with Ocean View & Garden

4.94 out of 5 average rating, 142 reviews

Kaanapali Fairway Vista - Legal STR Hotel Zoned

A studio space features a spacious bed adorned with a neutral-colored duvet and decorative pillows. A comfortable seating area, equipped with a couch and a small table, is present. A ceiling fan and wall-mounted TV are also visible, enhancing the room's functionality.

4.99 out of 5 average rating, 286 reviews

Modern studio by the beach - Taxes included

A covered lanai features two comfortable chairs facing the ocean. In the background, vibrant foliage borders the lush lawn, with the serene sea meeting the horizon. A welcoming sign is displayed on the wall, while a beautiful sunset casts warm hues in the sky.

4.94 out of 5 average rating, 100 reviews

Seaside Serenity: Oceanfront 1BR Suite

4.89 out of 5 average rating, 323 reviews

A pool area features a clear blue swimming pool surrounded by sun loungers. Lush palm trees are positioned along the perimeter, providing shade. A neighboring property and colorful tropical landscaping can be seen in the background under a bright blue sky.

Flat in Lahaina

The Sunset Stowaway—A Peaceful Napili Ridge Studio

4.98 out of 5 average rating, 111 reviews

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.

Holiday home in Lahaina

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt

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.