Cottage holiday rentals in Kaanapali

An intricately carved wooden front door is framed by two decorative pedestals, each featuring a plant arrangement that includes tropical foliage. The entrance is highlighted by a welcome mat on a wooden deck, exuding a warm and inviting entryway.

4.99 out of 5 average rating, 90 reviews

Ho'okipa Rose - Peace and Serenity

E Komo Mai! Ho'okipa Rose, Peaceful, Tropical home in the quaint town of Haiku. Lovely 2 bedroom, 2 bath, 1000 sq. ft. cottage located on private, two acre property. Fully equipped kitchen with everything you need to prepare meals. Upscale amenities throughout. Outdoor shower and infrared sauna. Beach chairs, towels, boogie boards and other beach items. 5 minutes from the famous Ho'okipa & Jaws! 10 minutes from the charming town of Paia and beaches. Enjoy Maui away from the busy touristy areas.

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4.95 out of 5 average rating, 455 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.

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4.93 out of 5 average rating, 149 reviews

Cottage in Kaanapali

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

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5 out of 5 average rating, 42 reviews

A charming retreat is nestled in a natural setting, surrounded by lush greenery and mountains. The structure features a distinctive green roof, with warm lights glowing from windows. A cozy seating area is visible on the porch, inviting relaxation amid serene surroundings.

Cottage in Wailuku

Romantic and Private Cottage and Gazebo for two!

Romantic, Private, a Sanctuary, beautifully decorated, local charm and sleeping to the sounds of Wailuku River are a few things our guests say about our Inn. An American Whirlpool hottub is our newest feature amenity along with the air conditioning, washer/dryer, full kitchen and a large shower in your private bathroom. A king Size bed, Wifi, barbeque grill, television, fans beach towels are standard amenities. The detached Gazebo is perfect for reading, meditating, or just doing nothing!

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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.

4.96 out of 5 average rating, 104 reviews

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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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.

4.83 out of 5 average rating, 219 reviews

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.

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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.

4.99 out of 5 average rating, 218 reviews

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

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4.96 out of 5 average rating, 113 reviews

A view from the property features a terracotta-tiled roof in the foreground, framed by lush green foliage. In the distance, the vast blue ocean is visible, along with the silhouettes of neighboring buildings and gently swaying palm trees against a backdrop of rolling hills.

Cottage in Kaanapali

Charming Kaanapali cottage with ocean view

A charming "Old Hawaii" bungalow on lush landscaped tropical grounds, only a ten minute walk from Kaanapali Beach, the best beach in West Maui. Close to numerous restaurants and shops in the Kaanapali area. But so beguiling is the view of Lanai and Molokai islands as you drink your morning coffee, so inspiring the sunsets as you sip your cocktail in the late afternoon--you may never leave the lanai!

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4.84 out of 5 average rating, 49 reviews

An open kitchen and living area is highlighted by a sleek countertop and warm wooden cabinetry. Large windows offer views of the ocean and beach, while a comfortable seating nook enhances the space. Natural stone flooring adds texture to the room.

Cottage in Kaanapali

OCEAN VIEW Kaanapali Cottage ICC 24

With a full OCEAN VIEW this cottage is a mere 5 minute walk from the local favorite "Kahekili Beach Park" offering great snorkeling & miles of pristine white sand beach's. There is a beachfront boardwalk & paths for walking, exercising in both directions accessing shopping (Whalers Village) & restaurants. ITS A PERFECT PLACE FOR ANYONE WANTING TO GET AWAY WEEKLY DISCOUNT

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4.99 out of 5 average rating, 239 reviews

A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.

Cottage in Makawao

Rustic Upcountry retreat with breathtaking views!

Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!

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The exterior of a cottage is shown, featuring a mix of light and dark pink siding. Solar panels are installed on the roof. Lush green landscaping surrounds the property, with palm trees and bushes enhancing the tropical ambiance. A concrete driveway leads to a covered entryway.

4.98 out of 5 average rating, 104 reviews

Leilani's "Leimomi" Cottage - County Licensed

Maui County License: STPH2013/0020 (taxes are included in rate) The home is part of the county licensed Leilani vacation rental property. The cottage is about 650 square feet with open beam ceiling and lots of windows and sliding doors with ocean views. Other amenities are a king size bed, full kitchen, outside covered sitting area with Jacuzzi , BBQ and lawn chairs.

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A quaint blue cottage is surrounded by lush greenery and vibrant red tropical plants. Large windows reflect the natural light, and the front porch invites relaxation. The well-maintained lawn complements the charming exterior, enhancing the cottage's appeal in its serene setting.