Vacation rentals in Haliimaile

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Top-rated vacation rentals in Haliimaile

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Guest favourite

A lush green expanse of agricultural land is framed by various trees, including tall palms and fruit-bearing varieties. The vibrant landscape leads to an unobstructed view of the ocean, with soft blue waters extending under a clear sky scattered with clouds.

Farm stay in Hana

Hana Nautilus- Ocean view 3 bed 2 bath family home

SUP 2019/0006 STHA20200001 Hawaii TA Tax:TA-081-974-0672-01 Hawaii GE Tax:GE-081-974-0672-01R Located in Hana, Maui this custom built 3 bedroom 2 bathroom ocean view house is situated on 2.8 acres of agricultural land. The land is abundant with seasonal fruit trees the guests may enjoy when available. The owners are delighted to offer helpful information so you can have a safe and enjoyable experience. Hana offers amazing adventures such as hiking, diving, swimming, surfing and stunning beaches

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 210 reviews

Top guest favourite

A charming cottage is nestled among lush tropical foliage, illuminated by warm lights from within. The peaked roof and extensive windows create an inviting atmosphere, while a spacious deck offers a glimpse of the surrounding nature, enhancing a serene setting under the dusk sky.

Home in Makawao

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

ValueLocationAccess

4.99 out of 5 average rating, 169 reviews

Top guest favourite

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 12 years with over 1,500 five star reviews. BUT 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: "The Jewel is extraordinary! The views are stunning! I’ve stayed in many Air B&Bs. I give her place my highest rating!" Btw, we have not raised our prices. The service fee now shows.

LocationFamilyLong stay

4.93 out of 5 average rating, 423 reviews

Top guest favourite

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.

Farm stay in Haiku-Pauwela

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

FamilyLocationCleanliness

4.94 out of 5 average rating, 689 reviews

Guest favourite

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.

FamilyValueParking

4.9 out of 5 average rating, 175 reviews

Guest favourite

A two-story green house with white trim is framed by vibrant pink bougainvillea and a gentle rainbow in the sky. A wooden deck wraps around the house, featuring lounge chairs positioned on the lawn, providing a relaxing outdoor space.

Guest suite in Makawao

Spectacular Ocean Views • Private Studio• King Bed

Ocean View Studio • Private Lanai • Peaceful Upcountry Maui Retreat Wake up to breathtaking panoramic views stretching from Maui’s North Shore and Central Valley to the West Maui Mountains and majestic Haleakalā. Enjoy your morning coffee on your private lanai with Maui Tradewinds - breezy days, cool evenings and a peaceful side of Maui that many visitors never experience. Sugar Shack Maui offers an authentic island experience just minutes from everything.

LocationFamilyWalkability

4.93 out of 5 average rating, 210 reviews

Top guest favourite

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.

FamilyLocationLong stay

4.94 out of 5 average rating, 543 reviews

Guest favourite

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.

LocationValueShared spaces

4.83 out of 5 average rating, 220 reviews

Guest favourite

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.

Guesthouse in Haiku-Pauwela

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.

LocationValueKitchen

4.93 out of 5 average rating, 153 reviews

Top guest favourite

A modern, two-bedroom home is showcased, featuring a covered lanai with a dining area for six. Large windows provide views of the surroundings, while the exterior combines wood and blue siding against a bright sky and greenery.

Home in Haiku-Pauwela

Peaceful and Spacious; North Shore Maui

New, spacious two-bedroom home in Ha'iku, Maui (Permit STPH20200003). With beautiful ocean views and peaceful surroundings, located on the Northshore of Maui, this is the perfect place to stay to explore the Road to Hana, the Northshore, and upcountry Maui. Perfect for two couples or a family, you'll have everything you need to explore the island and a peaceful living area to relax following a day of adventuring.

ValueLocationNearby

4.98 out of 5 average rating, 163 reviews

Top guest favourite

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.

Guesthouse 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

LocationFamilyParks

4.95 out of 5 average rating, 128 reviews

Top guest favourite

A panoramic view showcases lush green landscape merging into the blue ocean on the horizon. A variety of trees, including a tall conifer, adds to the natural beauty. The sky is bright with scattered clouds, creating a serene atmosphere.

Home in Haiku-Pauwela

Charming Hoku Pauwela Breathtaking ocean views!

Located on the north shore of Maui, Hoku Pauwela (Maui County B&B Permit# BBPH 2019/0002 and Hawaii State TAT # TA-036-968-8576-01) is the ideal location from which to experience the north shore, upcountry, Haleakala crater, and the epic drive to Hana. Spacious, quiet, and family-friendly, you'll have all you need to explore Maui and a peaceful living area to relax in after a day of adventuring.

LocationFamilyDecor

4.99 out of 5 average rating, 210 reviews