Cottage vacation rentals in Kaanapali

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Top-rated cottage rentals in Kaanapali

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Guest favorite
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
4.83 out of 5 average rating, 46 reviews

OCEAN VIEW Kaanapali Cottage ICC 24

OCEAN VIEW top of the property adjacent to the 12th fairway of the Royal Kaanapali Golf Course. This Kaanapali Cottage with 2 beautiful swimming pools is a mere 5 minute walk from the local favorite "Airport Beach", featuring world-class 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

Top guest favorite
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
4.96 out of 5 average rating, 430 reviews

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.

Top guest favorite
An inviting outdoor living area features wooden seating arrangements adorned with plush cushions. Lush greenery surrounds the space, and decorative string lights create a warm ambiance overhead. A shaded daybed offers a comfortable spot for relaxation amid the tropical landscape.
Cottage in Kaanapali
4.93 out of 5 average rating, 147 reviews

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.

Top guest favorite
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
5 out of 5 average rating, 32 reviews

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!

Top guest favorite
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
4.99 out of 5 average rating, 208 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

Top guest favorite
A charming cottage is set amidst lush tropical foliage, featuring a well-maintained path leading to a white staircase. Green plants and trees frame the entrance, creating a serene and private environment for guests.
Cottage in Kihei
4.97 out of 5 average rating, 126 reviews

One Block to the Beach! Cozy Beach Cottage Kihei

Welcome to Chez Maui! This cozy 2-bedroom, 1-bathroom cottage is just one block from the beach, offering a peaceful and private retreat. Perfect for your vacation or for remote workers, traveling healthcare professionals, snowbirds or those in transition to longer-term accommodation. The cottage comfortably hosts up to 4 guests maximum and has been recently renovated. *Make sure to turn on your notifications for Airbnb Messaging.*

Top guest favorite
A serene sunset is depicted over the ocean, with vibrant hues of orange and yellow radiating from the setting sun. Rays of light extend outward from the sun, casting a gentle glow across the water's surface, creating a tranquil coastal scene.
Cottage in Kihei
5 out of 5 average rating, 13 reviews

Grateful Casita

Welcome to Grateful Casita — a well-loved local home with driveway, private yard, and quiet neighborhood. Real local living, upgraded with a king sized bed! 🛏️😴 Nestled beneath Maui's blue sky, wrapped in lush tropical greenery — this humble Casita is small in size but enormous in heart. Your own soft place to land. 🛬 May your good energy, warm aloha, and peaceful moments find your way to our humble Casita. 🙏🏡

Top guest favorite
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
4.96 out of 5 average rating, 107 reviews

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!

Top guest favorite
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
4.99 out of 5 average rating, 231 reviews

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!

Top guest favorite
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.
Cottage in Haiku
4.98 out of 5 average rating, 102 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.

Top guest favorite
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.
Cottage in Haiku
4.95 out of 5 average rating, 275 reviews

Great Location, 1 BR Beachy, VERY CLEAN Cottage

COUNTY PERMITTED - This home holds legal Maui Permit STPH2015/0006. Amazing Haiku location, Very Clean, Cute Beachy-style, 1BR/1BA cottage home. 1 Queen bed very comfortable, quick walk to Haiku Grocery, Haiku Cannery, Nuka Sushi, Haiku Mangala Yoga, Colleen's, Short 4 mile drive to Ho'okipa, (sleeps 1-2) well equipped kitchen & new appliances

Top guest favorite
The modern cottage is surrounded by lush tropical foliage, featuring a carport that provides shaded parking. A well-manicured lawn showcases an array of plants. A vibrant sunset casts warm hues across the sky, highlighting the serene environment.
Cottage in Haiku-Pauwela
4.97 out of 5 average rating, 141 reviews

Private Country Cottage, Ocean View, A/C, Hana Hwy

Relax & enjoy the peace & quiet, coastal ocean views lush tropical setting & complete privacy at your modern cottage with private lanai. Palm Cottage is ideal for a quiet vacation, honeymoon or just a peaceful getaway. Come to quiet, rural Maui to get away from the crowds; yet only a few minutes drive from shops, restaurants & beaches.

Popular amenities for Kaanapali cottage rentals

Quick stats about cottage rentals in Kaanapali

  • Nightly prices starting at

    Kaanapali vacation rentals start at ﺩ.ﺇ881 per night before taxes and fees

  • Verified guest reviews

    Over 540 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Kaanapali rentals

  • 4.8 Average rating

    Kaanapali stays are highly rated by guests—averaging 4.8 out of 5!

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