Cottage vacation rentals in Kaanapali

Find and book unique cottages on Airbnb

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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, 10 reviews

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

MaileRating, 5 stars3 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 stars4 weeks 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, 87 reviews

Leilani's "Leimomi" Cottage - County Licensed

KatyRating, 5 stars4 weeks ago
Great place for exploring Maui, especially if you want to get away from the resorts and enjoy a cute Hawaiian town and upcountry. Margit’s place has everything you need (full kitchen, lanai, beach towels, w/d, filtered water….). Her cottage is well taken care of and in a beautiful, peaceful setting. Top notch.
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
4.82 out of 5 average rating, 203 reviews

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

MattRating, 5 stars2 weeks ago
We loved our stay at the Dragonfly cottage. The kids loved running around in the jungly surroundings and evenings in the hot tub or jacuzzi bath. We loved hearing the rain at night. This was the best stocked Airbnb we’ve ever stayed at and appreciated our local welcome basket. We had boogie boards and fins and games and were very well entertained. Ha’iku and Makawao are both so close and both have great food. My only annoyance was the neighboring rooster that started crowing a few hours before sunrise. But the cottage was a total delight!
Top 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, 262 reviews

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

MackenzieRating, 5 stars1 week ago
Celebrated our honeymoon and was the only perfect place to stay as a couple. Beautiful inside but absolutely stunning backyard! The hosts were amazing and responsive! Would definitely recommend
Superhost
Cottage in Kihei
4.83 out of 5 average rating, 86 reviews

Romantic Suite | Tropical Escape | BBQ & Hot Tub

SimonaRating, 5 stars1 month ago
We had a great stay at Alexandra’s. The apartment is very cute and clean, and it’s in a great location to enjoy Kihei. Just a few minutes driving from all the restaurants and beaches. At the same time, the neighborhood is very quiet and we woke up every morning with the sounds of birds singing.
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, 196 reviews

Luxury Upcountry retreat with breathtaking views!

JamesRating, 5 stars2 weeks ago
We wish we could have stayed longer. David a Dawn put a lot of hard work into the space. The pool/hottub and sauna were very clean and enjoyable. The Jungalow itself felt very private and great sunset. Everything you could need is there for you kitchen, bathroom, fireplace, plenty of seating everywhere . The open air and big windows make you feel like you’re living outside. The porch and balcony were great for relaxing on. Plenty of parking and easy to get in and out. The property itself is gorgeous. Great flowers plants and trees, smelled great everywhere you went. Plenty of places to go from the property and they were very helpful in telling us the best spots to check out. Thanks for sharing your house with us Dave and Dawn!
Top 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
4.97 out of 5 average rating, 202 reviews

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS

RebeccaRating, 5 stars1 week ago
If you are looking for a peaceful, adventurous, romantic getaway… this little cottage is the place you’ll never forget. You hear birds surrounded by a lush landscape, can see stars while soaking in the hot tub after your day of adventures, Cliff walk everyday, outdoor showers, fresh eggs and flowers make you feel like you are off the beating path. Great location to explore the island. Outstanding food, beach, and massage recommendations by Sharyn. We felt at home and it was hard to leave. We hope to return some day.

Private cottage rentals

Top guest favorite
A well-maintained wraparound deck features comfortable seating under a striped umbrella. Lush tropical landscaping with vibrant flowers surrounds the space, enhancing the natural beauty. A grill is positioned adjacent to the seating area, providing an inviting space for outdoor dining.
Cottage in Kihei
4.98 out of 5 average rating, 51 reviews

Maui Meadows Ocean View Cottage

GrittRating, 5 stars4 months ago
We absolutely loved the cottage! Tom and Denise were very kind and gave us a lot of helpful information on activities and restaurants in the area. The cottage had great extras like snorkeling gear, beach towels etc. In the morning, we were woken up by the beautiful sound of birds which we will miss dearly back home! We were super happy a late check-out was possible as our flight was in the evening. Highly recommend booking with Tom and Denise (and their adorable dog), would 100 percent book again!
Top 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, 262 reviews

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

MackenzieRating, 5 stars1 week ago
Celebrated our honeymoon and was the only perfect place to stay as a couple. Beautiful inside but absolutely stunning backyard! The hosts were amazing and responsive! Would definitely recommend
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 stars1 week 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!
Guest favorite
A charming cottage is surrounded by lush greenery, featuring a stone facade and wooden accents. Large windows allow warm light to shine through, creating a welcoming atmosphere. The entryway is framed by tropical plants and a compact stone path that leads to the door.
Cottage in Makawao
4.94 out of 5 average rating, 626 reviews

Adorable Garden Gingerbread House

Rocky & KristieRating, 5 stars2 weeks ago
What an oasis! Lush, private, & peaceful. A favorite was picking fresh guava for breakfast! Eve was attentive but not over bearing, kind and hospitable. We really felt like we could explore and enjoy the entire grounds. And the sanctuary next door was simply beautiful and a quick walk away. You can even buy an “over the top” fresh exotic flower bouquet for $18!! We grilled out on the back patio and soaked it all in . We’d definitely recommend this get-away!
Top guest favorite
The spacious bedroom features a large bed with white linens and green accents. A tray with a candle is placed on the bed. Floor-to-ceiling windows offer a view of the sunset, while a cozy seating area with two chairs is visible on the balcony.
Cottage in Makawao
4.99 out of 5 average rating, 196 reviews

Luxury Upcountry retreat with breathtaking views!

JamesRating, 5 stars2 weeks ago
We wish we could have stayed longer. David a Dawn put a lot of hard work into the space. The pool/hottub and sauna were very clean and enjoyable. The Jungalow itself felt very private and great sunset. Everything you could need is there for you kitchen, bathroom, fireplace, plenty of seating everywhere . The open air and big windows make you feel like you’re living outside. The porch and balcony were great for relaxing on. Plenty of parking and easy to get in and out. The property itself is gorgeous. Great flowers plants and trees, smelled great everywhere you went. Plenty of places to go from the property and they were very helpful in telling us the best spots to check out. Thanks for sharing your house with us Dave and Dawn!
Top guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances, with an island bar seating area highlighted by four rattan stools. Pendant lights hang from the ceiling, illuminating the space. A potted orchid adds a touch of greenery to the counter.
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 190 reviews

North Shore Ocean View Cottage

JuliaRating, 5 stars2 weeks ago
We love it here. Brigitte and Dave could not be more kind and hospitable. Their cottage is wonderful - spotless and with everything you might wish for on Maui. Always hard to leave 💗 Endless thanks!
Guest favorite
A view of the lush garden is captured, showcasing a variety of tropical plants and trees. In the distance, structures blend harmoniously with the greenery, while the sky is adorned with scattered clouds, enhancing the tranquil atmosphere of this private retreat.
Cottage in Maui County
4.92 out of 5 average rating, 222 reviews

Ualani Retreat. Private Ocean View Cottage.

EmilyRating, 5 stars2 weeks ago
Loved this quiet spot! It was comfortable, had all we needed and was so peaceful. Would definitely recommend!
Top guest favorite
Cottage in Haiku-Pauwela
4.97 out of 5 average rating, 127 reviews

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

VibhuRating, 5 stars3 weeks ago
It was fun staying at Stephnie and Robert’s place. They was very responsive and answered all our questions quickly. They even offered us to setup and barbecue. The location was perfect for road to hana and the place was peaceful and lush green.

Luxury cottage rentals

Top guest favorite
A shaded lounge area features two wooden chaise lounges with green cushions positioned beneath a large umbrella. Nearby, a covered gazebo includes a dining table and chairs, surrounded by lush tropical vegetation and vibrant plants.
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 83 reviews

Ho'okipa Rose - Peace and Serenity

MartinRating, 5 stars2 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!
Top guest favorite
The exterior of a renovated cottage is displayed, featuring a spacious lanai with patio furniture shaded by an umbrella. Lush greenery and colorful flowers frame the entrance, enhancing the tranquil setting. Large windows invite natural light into the interior space, showcasing an inviting atmosphere.
Cottage in Kihei
5 out of 5 average rating, 54 reviews

Beautiful Beach Cottage: lush garden paradise

JenniferRating, 5 stars3 months ago
We love Maui and are so thrilled to have found such a lovely place to stay. Katherine and Dean couldn’t have been more welcoming, helpful and kind. Kihei is a terrific base for exploring and enjoying the island. As we drove out to head to the airport, we all said it was the best Airbnb experience we have had (among many wonderful Airbnb experiences and basically no bad ones). We will be back! :)
Guest favorite
A sandy pathway bordered by lush greenery leads to a serene beach. Vivid blue ocean waters gently lap against the shore, with soft waves rolling in under a clear sky dotted with fluffy white clouds.
Cottage in Paia
4.84 out of 5 average rating, 83 reviews

Charming Cottage in Kuau

E.P.Rating, 5 stars10 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!!!
A serene swimming pool is framed by lush tropical vegetation and tall palm trees. A waterfall cascades down a rock formation into the pool, while a waterslide is visible on the side. The sky above is bright with scattered clouds.
Cottage in Kihei
4.96 out of 5 average rating, 25 reviews

Private 2 bedroom cottage with pool

AlmaRating, 5 stars14 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 exterior of a two-story cottage is featured, set against a backdrop of palm trees and coastal vegetation. A staircase leads down to the rocky shoreline, while lounge chairs are arranged on the grass near the cottage, inviting a relaxing outdoor experience.
Cottage in Paia
4.73 out of 5 average rating, 216 reviews

Lani Paradise Oceanfront Cottage

NoahRating, 5 stars1 month ago
Beautiful location. Secluded and set back from the road with an incredible ocean view. House had all the essentials. Would love to come back.
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, 96 reviews

Kaanapali Spacious Cottage Walk to the Beach ICC30

MalorieRating, 5 stars4 months ago
We all enjoyed the Airbnb ! Very spacious place and convenient.
A serene beachfront is depicted, showcasing golden sand meeting clear blue waters. Gentle waves lap at the shore, and palm trees sway in the breeze, framing the scene. In the distance, small boats can be seen on the horizon under a bright blue sky.
Cottage in Lahaina
4.71 out of 5 average rating, 56 reviews

Pono Plantation Maui-3 Bedroom Cottage

AndresRating, 5 stars15 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!
Superhost
A stone pathway leads through lush tropical greenery, including tall palm trees and vibrant foliage. The two-story home is visible in the background, surrounded by the natural beauty of the landscaped garden.
Cottage in Haiku-Pauwela
4.97 out of 5 average rating, 62 reviews

Haiku Nani, County Licensed

SarahRating, 5 stars2 months ago
This home is stunning! The gardens around the home are more beautiful and peaceful than the photos and the house was absolutely perfect for two couples. The small towns of Haiku-Pauwela, Pa'ia, and Makawao are wonderful and have so much character. The management team, Margit and AJ, were incredibly helpful and kind. There was a big storm on the islands the day we were to depart - flight cancelled, power outages, flooding, etc. They welcomed us back to the house for 3 more nights (we couldn't get a flight out until then). Margit and her husband offered to come pick us up at the airport and bring us back to the house, brought lanterns and flashlights to the house since there was no power... all during a crazy storm! We felt so taken care of and they were so kind. AJ in the office helped out with the rebooking for the 3 nights... SO MUCH ALOHA, all around!! We would DEFINITELY come stay here again. Mahalo!!

Quick stats about cottage rentals in Kaanapali

  • Total rentals

    10 properties

  • Nightly prices starting at

    $210 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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