Cottage vacation rentals in Kaanapali
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Kaanapali
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kaanapali cottage rentals
Cottage rentals with a hot tub
Cottage in Haiku-Pauwela
5 out of 5 average rating, 9 reviewsPrivacy, Luxury, Ocean View Cottage, HotTub, K-Bed
Nothing beats keeping the windows open all night, having coffee on the deck (with a lovely, calming view), and outdoor showers! Hank’s place was comfortable and peaceful. Perfect for a relaxing week.
Cottage in Wailuku
5 out of 5 average rating, 12 reviewsRomantic and Private Cottage and Gazebo for two!
Tamara was very welcoming and gave us a walk through of the Airbnb right when we arrived. She also left us some delicious banana bread! The Airbnb had everything we needed, down to beach gear that came in handy! The unit was private and beautiful.
Cottage in Kihei
4.81 out of 5 average rating, 73 reviewsHoneymoon Suite, Tropical Getaway - BBQ, Hot Tub
The description was spot on! Great place to stay and great location to things to do and places to eat! The place was spacious and clean! The host was willing to help us with any questions we had and gave us recommendations! They checked in too! The backyard was awesome and so cute! They had a laundry room too and a drying rack which came in handy! Host gave details on how to check in and check out which was so easy to follow! Would recommend to anyone needing to stay somewhere in Maui!
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 78 reviewsLeilani's "Leimomi" Cottage - County Licensed
The house is absolutely beautiful! Peaceful setting, kitchen was outfitted with everything possible, back yard is ideal for star gazing (which we did every night). A lot of nice "extras" that made the stay special. Perfect place to explore the amazing island and all that it offers - beaches, hiking, relaxing.
Private cottage rentals
Cottage in Paia
4.71 out of 5 average rating, 21 reviewsWalk to small beach, charming cottage
We felt at home, like we were local to the area. Easy drive to Paia just a mile up the road. Next door to Mama’s Fish House which we’d booked in advance…a real treat. Easy drives to Baldwin Beach and others. Lovely.
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 78 reviewsHo'okipa Rose - Peace and Serenity
We had a wonderful stay at Rosa & Karl's gorgeous space. Both were fantastic, kind, and helpful hosts and the rental was absolutely amazing. The property is gorgeous and we really enjoyed the back lanai area. The place was immaculate and well appointed. It truly had everything you need and more. It is located close to great beaches and lots of dining establishments and shops. We were able to have groceries delivered via Instacart which was a great time saver for us. The kitchen was stocked with everything you need to cook anything. The coffee maker and coffee pods were enjoyed by all and the deionized water was a great amenity as well. I enjoyed having AC units in each bedroom as well as the living space. Staying at Ho'okipa Rose made our visit to Maui wonderful. I hope we can get back to Maui and stay here again. Rosa & Karl, we appreciate you so much! Thank you.
Cottage in Kihei
5 out of 5 average rating, 52 reviewsBeautiful Beach Cottage: lush garden paradise
A truly fabulous stay in Maui. Katherine and Dean’s cottage is perfectly located for beautiful beaches, great restaurants and easy access to the airport and island attractions. The cottage was a perfect size for our family of 4 (2 adults, 2 children). The beds were comfortable, showers inside and out excellent and kitchen well-stocked with everything you could need. Our boys loved all of the beach toys/snorkel equipment available and it was great to have beach towels, chairs and umbrellas at our disposal. Whilst the place was perfect, our hosts made the trip special. They made our 2 boys feel like family, running around every morning with them to find fresh fruit in the garden and pointing out the turtles and rays swimming past their beautiful lawn. Dean and Katherine, thank you for making our final vacation in the States such a memorable one. We hope to return to Maui in the future.
Cottage in Kihei
4.98 out of 5 average rating, 49 reviewsMaui Meadows Ocean View Cottage
We had a wonderful time staying with Tom and Denise!! We brought our small dog with us from the mainland and she was most welcome at the cottage. The cottage has a wonderful view, charming furniture, a fully stocked kitchen and bathroom. The lanai was great for a sunset glass of wine. Tom and Denise were so sweet in giving us welcoming information. The cottage is very close to Wailea and all its dining and shopping options. We look forward to our next stay in their cottage!!
Cottage in Paia
4.84 out of 5 average rating, 83 reviewsCharming 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!!!
Cottage in Lahaina
4.91 out of 5 average rating, 128 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
We had a great time in the cottage. Neighbors are friendly and open. Kitchen and Veranda was well equipped, also snorkeling equip. available. Due to high temps during the day the wind as well as the installed fans could hardly cool down the temp at night below 25 degree celsius. Overall a great relaxing stay for us.
Cottage in Paia
5 out of 5 average rating, 97 reviewsLunaHouse In The Heart of Paia
We loved staying at Jim’s place! It was clean, comfortable and well appointed. Great location and fantastic outdoor patio bbq area! His attention to detail and thoughtful amenities were very much appreciated. We can’t wait to return! Mahalo Jim!
Cottage in Lahaina
4.66 out of 5 average rating, 91 reviewsKaanapali Spacious Cottage Walk to the Beach ICC30
Carol was extremely accommodating despite a few issues we encountered with AirBNB's app on the phone. Aside from that hiccup that affected the easiness of self-check in, everything was smooth sailing, the AC units definitely came in handy with the heat we weren't used to, and it was nice having a separate space/room for everyone! It was also super nice to be so close to the beach right across the street. Would definitely recommend this place in Maui.
Luxury cottage rentals
Cottage in Maui County
4.79 out of 5 average rating, 156 reviewsHoneymoon Haven: Ocean Vista & Bamboo Temple Bliss
Can’t say enough about how great of a time we had here. The scenery alone made our entire trip. Sitting on the porch in the morning and having coffee with whales jumping in the ocean in front of us was something I’ll never forget. And waking up in bed to the sun rising over the ocean. We absolutely plan to be back.
Cottage in Lahaina
4.95 out of 5 average rating, 22 reviewsPuamana: New, bright, clean, modern gem!
This is a beautiful property in an incredible location and the owners go out of their way to make guests comfortable Would book here again with zero hesitation. Especially great if you have kids or teenagers
Cottage in Lahaina
4.71 out of 5 average rating, 56 reviewsPono 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!
Cottage in Kihei
4.92 out of 5 average rating, 24 reviewsRemodeled 2BR | Deck | Washer/Dryer
I travel for work. The location was a little further North than I would have liked but it was so perfect that it made the extra traffic and driving worth the trade. " The kitchen, the coffee pot, the laundry facilities... It was just lovely.
Cottage in Kihei
4.96 out of 5 average rating, 25 reviewsPrivate 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!
Cottage in Maui County
4.77 out of 5 average rating, 71 reviewsThai Hale: Eco Retreat with OCEAN VIEW & Waterfall
A beautiful little spot in the world. Peaceful, away from any crowds or traffic. We enjoyed the sunrises from the porch everyday and cool breezes. Quite comfortably furnished and stocked cabin, good kitchen. Nice hot water in that outdoor shower. There is lots of natural beauty to see on foot around nearby. The hikes mentioned on site are pretty steep and intense, come prepared with proper shoes and leave some time. You'll need to drive to make the most of the location -- for good swimming/sandy beaches or down to Paia town and the best of the north shore, or up the mountain for a different climate. But nothing is too far. Just a real nice part of the island to take it easy and completely lax. Hosts were very responsive to any needs, including fresh eggs from the chickens. Would stay again.
Cottage in Paia
4.72 out of 5 average rating, 211 reviewsLani Paradise Oceanfront Cottage
The views from this home are stunning! The house was built with fine detailing and high quality construction. I enjoyed the yard space, perfect spot for yoga! It is an efficient space, but accommodated our group of two adults and two children perfectly. The pool was also a really nice place to make friends and play water games.
Quick stats about cottage rentals in Kaanapali
Total rentals
10 properties
Nightly prices starting at
$200 before taxes and fees
Total number of reviews
650 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
- Cottage rentals Hawaii
- Cottage rentals Maui
- Villa rentals Kaanapali
- Hotel rentals Kaanapali
- Beach house rentals Kaanapali
- Monthly Rentals Kaanapali
- Rentals with an EV charger Kaanapali
- Serviced apartment rentals Kaanapali
- Fitness-friendly rentals Kaanapali
- Rentals with a sauna Kaanapali
- Rentals with a fire pit Kaanapali
- Rentals with a washer and dryer Kaanapali
- Rentals with outdoor seating Kaanapali
- Kid-friendly rentals Kaanapali
- Condo rentals Kaanapali
- Rentals with pools Kaanapali
- Family-friendly rentals Kaanapali
- Rentals with a hot tub Kaanapali
- Rentals with an accessible height bed Kaanapali
- Pet-friendly rentals Kaanapali
- Rentals with beach access Kaanapali
- House rentals Kaanapali
- Resort rentals Kaanapali
- Beach condo rentals Kaanapali
- Apartment rentals Kaanapali
- Beachfront rentals Kaanapali
- Rentals with breakfast Kaanapali
- Rentals with a kayak Kaanapali
- Rentals with a patio Kaanapali
- Waterfront rentals Kaanapali
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes