Cottage vacation rentals in Kaanapali

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Popular amenities for Kaanapali cottage rentals

Cottage rentals with a hot tub

A private cottage is nestled among vibrant tropical foliage along a gravel path. Lush greenery surrounds the home, showcasing a blend of colorful flowers and palm trees. The cottage features a welcoming porch, perfect for enjoying the serene garden views.
Cottage in Haiku-Pauwela
5 out of 5 average rating, 11 reviews

Privacy, Luxury, Ocean View Cottage, HotTub, K-Bed

MaileRating, 5 stars5 months ago
we enjoyed our week long stay at Hank's place. the area is beautiful and there is a lot to do. Hank had a number of useful kitchen amenities and was very friendly and accommodating! thank you!
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, 20 reviews

Romantic and Private Cottage and Gazebo for two!

HeatherRating, 5 stars2 months ago
We LOVED everything about this location. Iao Valley is so special and the location of the AirBNB itself was perfect for getting all around the island. We visited at the end of March and never ran the AC once. It was hot during the afternoon but the morning/late afternoon/evening cool off, with the winds blowing into the valley were so perfect. AND the birdsong in the morning was so beautiful that I recorded it and sent it to my family (minus the rooster song- but that's just Maui living for ya). If you want a good cocktail check out Ester's Fair Prospect, they have a nice selection of liquor and a fun vibe, located in the city of Wailuku right next door to this place. Also we loved the goodies that were left in the fridge. The pineapple on the island is SOOO good. Sooooooo good. Forget the banana bread hype... just eat the pineapples and bananas fresh! 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-Pauwela
4.98 out of 5 average rating, 89 reviews

Leilani's "Leimomi" Cottage - County Licensed

KatherineRating, 5 stars1 month ago
Margit's listening showed an availability for the time we would be traveling. Airbnb noted this fact as "a rare find", which turned out to be totally true! The home was spotless, well appointed, and welcoming. It was easy to get settled in with our luggage and groceries. The yard was beautifully landscaped and peaceful. The rental fee is very competitive. Margit replied to messages in a quick and friendly manner. We couldn't have been happier with our choice in lodging.
Superhost
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
4.83 out of 5 average rating, 210 reviews

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

GwennRating, 5 stars5 days ago
The house itself is beautiful and unique. The location is great. It is somewhat remote and generally with easy access to small towns and beaches within 10 to 15 minutes. The host was helpful and responsive. Hot tub was great and access to the pool was easy.
Guest favorite
A single-story cottage is surrounded by a lush tropical garden, featuring vibrant flowers and palm trees. A spacious green lawn invites relaxation, while the wooden deck area, partially shaded, offers a welcoming space for outdoor activities.
Cottage in Kihei
4.98 out of 5 average rating, 272 reviews

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

SarahRating, 5 stars6 days ago
This place was 5 stars all-around! Jenni provided everything we could think of - and more! This was the perfect stay for my partner and I, having that romantic Maui vacation feel. We hope to be back!! Mahalo!!
Superhost
Cottage in Kihei
4.83 out of 5 average rating, 87 reviews

Romantic Suite | Tropical Escape | BBQ & Hot Tub

VictoriaRating, 5 stars1 month ago
We stayed here for 10 days on our honeymoon. This was the perfect spot! Had a private backyard, a hot tub and it was so cozy for the 2 of us. It was close to all the food and all the beaches as well.
Guest favorite
Cottage in Makawao
4.99 out of 5 average rating, 200 reviews

Luxury Upcountry retreat with breathtaking views!

HarryRating, 5 stars1 week ago
My wife and started our honeymoon at this AirBnB. We spent three amazing days at the "Jungalow" house. We woke up every morning to a breathtaking view of the ocean from the cool and breezy mountainside of Haleakala, where the AirBnB is located. We just spent our time soaking in the surroundings each morning, and enjoying the French press coffee that was provided. We fell asleep each night to the sounds of wind and birds in the trees, and I even refilled the bird feeder near the downstairs window with host-provided bird seed. If you want a place to reset and be at peace with life, then this is the place that you need to go. My wife and I also found plenty of shopping just down the mountain in the nearby town of Makawao, and we explored many other parts of the island, too. Nothing is very far away from anything else in Maui. If you want an adventure, then you should go to the top of Haleakala like we did, or just stay at pool/sauna at the AirBnB :) This place is the real deal.
Guest favorite
An aerial view highlights the cottage nestled among lush greenery, showcasing solar panels on the roof. A private hot tub is set near outdoor loungers, with stone pathways leading through the vibrant tropical landscape.
Cottage in Maui
4.96 out of 5 average rating, 207 reviews

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS

NickRating, 5 stars1 week ago
What a lovely place! Soooo little bugs in a forest environment. Very clean! Sharyn is very responsive, always so welcoming and friendly! She made the place extra special for me and my wife. Will totally recommend her👍👍👍

Private cottage rentals

Guest favorite
A single-story cottage is surrounded by a lush tropical garden, featuring vibrant flowers and palm trees. A spacious green lawn invites relaxation, while the wooden deck area, partially shaded, offers a welcoming space for outdoor activities.
Cottage in Kihei
4.98 out of 5 average rating, 272 reviews

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

SarahRating, 5 stars6 days ago
This place was 5 stars all-around! Jenni provided everything we could think of - and more! This was the perfect stay for my partner and I, having that romantic Maui vacation feel. We hope to be back!! Mahalo!!
Top guest favorite
An outdoor dining area is set with a wooden table, featuring white plates, glassware, and candles. Lush greenery surrounds the space, with a sunset landscape in the background, casting a warm glow over the scene.
Cottage in Kula
4.96 out of 5 average rating, 361 reviews

HALEKALANI - Paradise in Upcountry

H. S. Rating, 5 stars2 months ago
We had a wonderful stay! The house was beautiful, with a lovely garden and a stunning view. Everything was clean, comfortable, and exactly as described. The host was very responsive and helpful throughout our stay. We enjoyed our time here and would definitely stay again. Highly recommend!
Top guest favorite
The cottage exterior is set against a backdrop of tropical vegetation and clouds. Palm trees and lush greenery frame the home, with a gravel path leading to the double carport. A view of the ocean can be glimpsed in the distance, enhancing the natural surroundings.
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 195 reviews

North Shore Ocean View Cottage

DebraRating, 5 stars1 week ago
We had the pleasure of staying at Dave and Bridgett’s home for two weeks while visiting family. This was one of the best stays ever! The home was spacious, immaculately clean, very well equipped for preparing meals and the hosts were so kind and welcoming. We would not hesitate to stay again. Mahalo for making this such an amazing experience.
Guest favorite
Cottage in Makawao
4.99 out of 5 average rating, 200 reviews

Luxury Upcountry retreat with breathtaking views!

HarryRating, 5 stars1 week ago
My wife and started our honeymoon at this AirBnB. We spent three amazing days at the "Jungalow" house. We woke up every morning to a breathtaking view of the ocean from the cool and breezy mountainside of Haleakala, where the AirBnB is located. We just spent our time soaking in the surroundings each morning, and enjoying the French press coffee that was provided. We fell asleep each night to the sounds of wind and birds in the trees, and I even refilled the bird feeder near the downstairs window with host-provided bird seed. If you want a place to reset and be at peace with life, then this is the place that you need to go. My wife and I also found plenty of shopping just down the mountain in the nearby town of Makawao, and we explored many other parts of the island, too. Nothing is very far away from anything else in Maui. If you want an adventure, then you should go to the top of Haleakala like we did, or just stay at pool/sauna at the AirBnB :) This place is the real deal.
Guest favorite
The image captures a coastal view of lush green mountains meeting the ocean. A winding road is visible, revealing a tranquil stretch of shoreline. Gentle waves lap against the rocks, and a clear sky is seen above, enhancing the serene atmosphere of this tropical landscape.
Cottage in Maui County
4.92 out of 5 average rating, 225 reviews

Ualani Retreat. Private Ocean View Cottage.

ArielRating, 5 stars1 month ago
Absolutely beautiful property. It was perfectly away from the hussle and bussle, but close enough to cute little towns, resturants, beaches, Hana HWY, the National Park. It was also nice to have some great amenities and extras for activities while we stayed. Having our own 'home' while on vacation without breaking the bank. We ran into John while he was outside with Grace (their adorable fur baby) and she was the sweetest as he was as well as my boyfriend asked questions and complimented on the property. They were respectful to not barge in on our time or hover. They gave great insturctions/recommendations posted on the fridge for pur stay as well. Would definitely stay here again if when i visit maui in the future.
Top guest favorite
Cottage in Haiku-Pauwela
4.97 out of 5 average rating, 129 reviews

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

DavidRating, 5 stars1 month ago
Very beautiful and peaceful cottage. Great location close to the Road to Hana and northern beaches. Easy to park vehicle in the carport and excellent from a logistics perspective during the week stay. Neighborhood was very quiet and good for relaxation. Owners great to work with and keep the place well managed. Thank you!
Guest favorite
The scene presents a rocky shoreline where dark volcanic rocks contrast with clear turquoise waters. Gentle waves roll onto the beach, and grassy land is visible in the distance, bordered by green hills that lead to mountains under a bright blue sky.
Cottage in Haiku-Pauwela
4.95 out of 5 average rating, 238 reviews

Great Location, 1 BR Beachy, VERY CLEAN Cottage

BenjaminRating, 5 stars3 days ago
Great little cottage, perfect for our stay and exploration of nearby Paia and Haleakala! Very clean with lots of nice touches, and Ally was super communicative and a wonderful host.
Guest favorite
Cottage in Kula
4.95 out of 5 average rating, 369 reviews

Oceanview Cottage away from heat! w/ County Permit

JaredRating, 5 stars3 days ago
Mei & Iris’s Oceanview Cottage worked out great for us! We were in town from Oahu and were looking for a quiet place to relax and enjoy nature. The cottage was very peaceful with amazing views! Our hosts were responsive to messages and provided a lot of local recommendations! We enjoyed our stay and wouldn’t hesitate to book again in the future!

Luxury cottage rentals

Guest favorite
Cottage in Maui County
4.8 out of 5 average rating, 160 reviews

Honeymoon Haven: Ocean Vista & Bamboo Temple Bliss

NissimRating, 5 stars2 months ago
Maui Eco Retreat was nothing short of magical. The energy on the grounds was something I never expected—calming, vibrant, and deeply rejuvenating. From the moment we booked, the pre-arrival communication made us feel completely at ease, setting the tone for an unforgettable stay.We arrived at 10 PM and were greeted by William, who welcomed us with such warmth and enthusiasm. His passion for the retreat was evident, making us feel instantly at home. We stayed for four nights in the Bamboo Temple, a serene sanctuary with the most breathtaking ocean and sunrise views. Waking up at 6 AM was effortless when rewarded with the golden light streaming through the massive bay window—an experience in itself. Our mornings started with a quick 10-minute drive to grab coffee before returning to our beautifully equipped room to prepare breakfast. The retreat had everything we needed, including a fully equipt kitchen. After breakfast, I would head to the yoga studio for a 60-minute flow, followed by
Top guest favorite
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.
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 83 reviews

Ho'okipa Rose - Peace and Serenity

MartinRating, 5 stars3 months ago
Rosa and Carl are wonderful hosts. They were very kind and helpful providing lots of tips for trips. Accomodation was perfect, refreshments waiting for us after long fly from Europe. Fully recommended. Mahalo!
Guest favorite
Cottage in Paia
4.84 out of 5 average rating, 83 reviews

Charming Cottage in Kuau near Mama’s Beach

E.P.Rating, 5 stars12 months ago
Had the best time! Thank you for a wonderful stay!! Such a bonus to meet the owners and feel so welcomed into their cozy space. We will come back if we can!!!
Superhost
A spacious interior features bamboo walls and a high, rounded ceiling. Two seating arrangements, including wicker chairs and a coffee table, invite relaxation. Large glass doors frame views of the outdoors, while soft natural light fills the room, enhancing the serene atmosphere.
Cottage in Maui County
4.75 out of 5 average rating, 73 reviews

Thai Hale: Eco Retreat with OCEAN VIEW & Waterfall

EllenRating, 5 stars3 months ago
Such a lovely and magical place to stay! So peaceful and quiet. William was the best. Extremely helpful and responsive! Will be back next year!
A tranquil pool area is shown, featuring a spacious pool surrounded by lush tropical plants. A covered seating area with wicker furniture sits nearby, providing a shaded space for relaxation. A water slide and natural rock feature add visual appeal, under a bright blue sky.
Cottage in Kihei
4.96 out of 5 average rating, 25 reviews

Private 2 bedroom cottage with pool

AlmaRating, 5 stars16 months ago
My family enjoyed staying in the cottage while on vacation. It has everything you need. The pool was perfect. My 12 year old son used the pool every day. The cottage is close to the beach, too. Best vacation so far!
Superhost
The cottage is surrounded by lush greenery, featuring large windows that offer views of the ocean. Two comfortable lounge chairs are positioned on the manicured lawn, inviting relaxation. The roofing structure presents a charming design, complemented by tropical plants that enhance the outdoor environment.
Cottage in Paia
4.73 out of 5 average rating, 217 reviews

Lani Paradise Oceanfront Cottage

NikiRating, 5 stars2 weeks ago
What can I say - this Airbnb is a 10/10! The hosts were super friendly and gave fantastic recommendations (as well as an amazing welcome basket!) They were also each to reach in case we had questions. The place is fully stocked with everything you could need for the beach and/or pool. The view alone was worth every penny. I hope one day to be back in this amazing place! What a beautiful and relaxing retreat.
An expansive living area is illuminated by natural light from large windows. A sectional sofa and a small dining table are visible, surrounded by greenery. Decorative elements include a wall art piece and a potted plant on a side table, enhancing the tranquil setting.
Cottage in Lahaina
4.64 out of 5 average rating, 97 reviews

Kaanapali Spacious Cottage Walk to the Beach ICC30

JoanieRating, 5 stars3 months ago
The area was great and quiet.
Cottage in Lahaina
4.71 out of 5 average rating, 56 reviews

Pono Plantation Maui-3 Bedroom Cottage

AndresRating, 5 stars17 months ago
Katherine was very helpful with recommendations of activities! She followed up to see if we made it safely to her home. Katherine’s home had all the amenities and more, including beach chairs, boogie boards and more things to take to the beach. She also checked up on us to see if we needed anything. Thank you!

Quick stats about cottage rentals in Kaanapali

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$43,936 GYD before taxes and fees

  • Total number of reviews

    670 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Wifi availability

    10 properties include access to wifi

Destinations to explore

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  4. Maui County
  5. Kaanapali
  6. Cottage rentals