
Cottage vacation rentals in Kaanapali
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Top-rated cottage rentals in Kaanapali
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Popular amenities for Kaanapali cottage rentals
Cottage rentals with a hot tub

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

Romantic and Private Cottage and Gazebo for two!
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!

Leilani's "Leimomi" Cottage - County Licensed
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.

Hawaiian DreamTemple- Tropical Oasis BBPH20120004
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!

Luxury Cottage,Saltwater Spa-Close to Beach,Dining
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

Romantic Suite | Tropical Escape | BBQ & Hot Tub
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.

Luxury Upcountry retreat with breathtaking views!
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!

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS
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

Maui Meadows Ocean View Cottage
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!

Luxury Cottage,Saltwater Spa-Close to Beach,Dining
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

HALEKALANI - Paradise in Upcountry
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!

Adorable Garden Gingerbread House
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!

Luxury Upcountry retreat with breathtaking views!
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!

North Shore Ocean View Cottage
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!

Ualani Retreat. Private Ocean View Cottage.
Loved this quiet spot! It was comfortable, had all we needed and was so peaceful. Would definitely recommend!

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

Ho'okipa Rose - Peace and Serenity
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!

Beautiful Beach Cottage: lush garden paradise
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! :)

Charming Cottage in Kuau
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!!!

Private 2 bedroom cottage with pool
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!

Lani Paradise Oceanfront Cottage
Beautiful location. Secluded and set back from the road with an incredible ocean view. House had all the essentials. Would love to come back.

Kaanapali Spacious Cottage Walk to the Beach ICC30
We all enjoyed the Airbnb ! Very spacious place and convenient.

Pono Plantation Maui-3 Bedroom Cottage
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!

Haiku Nani, County Licensed
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
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