Search Upcountry Maui Cottage Rentals from CA $361

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Browse Select Upcountry Maui Cottages

Outdoor dining
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, (225)
"You will feel right at home in this very clean, cozy lush environment. If you’re looking for a change of pace tucked in a beautiful environment look no further. My 15-year-old son and I stayed here for 4 nights and felt right at home. We enjoyed cooking in the kitchen, and although they could have a few more cooking items, we were able to make all of our favorite meals from home. I would highly recommend this place for any family and friends seeking a longer stay than most in Hana."
The price is CA $402
CA $761 total
includes taxes & fees
May 24 - May 25
Secluded cottage on Tropical flower farm
Beach
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, (160)
"Very nice no complaints would book again"
The price is CA $361
CA $698 total
includes taxes & fees
May 24 - May 25
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Sun loungers, beach towels
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
9.8 out of 10, Exceptional, (92)
"My wife and I enjoyed our stay at this Vrbo very much. The check in/check out was easy. The detached unit felt private and roomy. It was very clean. The place was as advertised. No surprises. Easy walk to Paia with its restaurants and shopping. Close to beaches and to airport. Good overall location on Maui."
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
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Property grounds
Evergreen Cottage @ Maui Adventure Villa.
9.8 out of 10, Exceptional, (143)
"Was very helpful and great with communication. Hopefully we will get to stay at John’s property again! Gorgeous location and perfect of you are planning on stay near paia."
Evergreen Cottage @ Maui Adventure Villa.
Fridge, microwave, oven, stovetop
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
9.8 out of 10, Exceptional, (14)
"My husband and I stayed here a few nights on our trip to Maui, and this was the perfect spot! It was a great location, close to the airport, central location on the island to go and do lots of fun activities, and overall a very pleasant stay! Thank you!"
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
SUMMER DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
10.0 out of 10, Exceptional, (168)
"The cottage was an ideal home for us while on Maui. It was clean and had everything we needed with great views and beautiful landscaping. Hank is a great host who is not intrusive but eager to make sure everything is going well with the stay. The location was very convenient for getting everywhere we wanted to go and was close to excellent restaurants. Everything about it was beyond expectations and made for a wonderful visit to Maui."
SUMMER DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Pool
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, (129)
"We had a nice stay. Nice and private place in a nice quiet neighborhood. The cabin came stocked with all the amenities one would need."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Beach nearby, sun loungers, beach towels
Great location between Hana Town and Hamoa Beach, private, family-friendly
9.8 out of 10, Exceptional, (208)
"Nice small house just outside Hana, but close to everything. 1min to food trucks and stores, 5min to two beaches (and Huli Huli Chicken). It is a good place to start for day trips to do all the road to Hana things without hurry and be the first at Waimoku Falls, Waiʻānapanapa State Park or Lava Tube. If we (family of 4) come back to Hana, we happily would stay here again."
The price is CA $397
CA $746 total
includes taxes & fees
Jun 11 - Jun 12
Great location between Hana Town and Hamoa Beach, private, family-friendly
On the beach
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
10.0 out of 10, Exceptional, (130)
"It was incredible. The view and uniqueness of this cottage and property are superb. My husband and I had never in our lives been to the islands until this stay. (10 day stay). We knew we wanted a quiet, non-resort property and this was perfect! Everything you could need or want is just a few minutes away by car. We even walked to a near-by restaurant which was wonderful! Sitting on the deck watching and hearing the gentle ocean waves and many birds was surreal. It was truly a vacation to...
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
Exterior
Cozy Maui 'Treehouse' with lovely views and amenities
10.0 out of 10, Exceptional, (87)
"The Treehouse suited my wife and me perfectly. I think it would be a challenge to fine a place that is more peaceful and tranquil, as far as a vacation rental in Kihei. It is also a nice place to view the sunsets."
Cozy Maui 'Treehouse' with lovely views and amenities
Fridge, microwave, oven, stovetop
3BR Beach Bungalow with 1967 International Scout!
10.0 out of 10, Exceptional, (4)
"Everything was great and we had a marvelous time! The accommodations were perfect and met our needs very well. I would love to come back again sometime!"
The price is CA $559
CA $1,285 total
includes taxes & fees
Jun 7 - Jun 8
3BR Beach Bungalow with 1967 International Scout!
Fridge, microwave, oven, stovetop
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
9.0 out of 10, Wonderful, (22)
"This place is huge for a one bedroom and within the price range we were looking for! The kitchen was well equipped with everything we needed since we cooked in the whole time. Lots of storage as well! It was nice to have outdoor seating as well. We really appreciated the washer and dryer (steps away) and beach chairs. Thank you!"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Exterior
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
10.0 out of 10, Exceptional, (189)
"This beautiful property is perfect for those that want to get away from the large resorts and have nice place to come home to after a day of swimming, snorkeling, or sightseeing. It has one of the best stocked kitchens to do your own cooking along with a ton extras for your beach adventures. We stayed 7 days with our 6 and 8 years girls and they never once said they were bored. They entertained themselves in the pool that is right out the back door and chased endless butterflies that little...
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
On the beach, sun loungers, beach towels
Now with optional car add-on
10.0 out of 10, Exceptional, (135)
"It is an amazing property. It’s combines views amenities privacy and above all the hosts are the most accommodating helpful, knowledgeable and out great human beings."
Now with optional car add-on
Property grounds
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
10.0 out of 10, Exceptional, (169)
"Our stay was amazing! Our hosts went above and beyond! Looking forward to coming back!!"
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
TV
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
9.4 out of 10, Exceptional, (30)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Sun loungers, beach towels
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
9.4 out of 10, Exceptional, (20)
"Based up previous review, we expected it to be simple, but clean and fully functioning. Surfaces were not all clean, some small things didn't work, and it was very difficult to communicate with the hosts (gave us no local contact email or cell # and VRBO app didn't work for contacting host). It would have been great to have some sort of cottage notebook with info about local areas, beaches, restaurants, and driving distances from house. No local info provided; had to search everything ourselves....
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
Pool
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
10.0 out of 10, Exceptional, (224)
"We had a great time staying in Hana and would love to stay here again."
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Sun loungers, beach towels
A unique dolphin cabin in Kaanapali!
9.2 out of 10, Wonderful, (88)
"Pros and cons to this stay. Pros are it's big, the location is great; I did like the shower a lot! Cons are there is no AC. Yes, I realize many places on Maui do not have AC. The descritions reads "open air" and it just didn't register with me at the time of booking. So if you are a person that is remotely hot natured, don't book this in May. Maybe January is a better month. We spent the first night to see if we could handle it and decided to move to a closeby resort the next morning. No, I...
A unique dolphin cabin in Kaanapali!
Fridge, microwave, oven, stovetop
Steps from the Ka'anapali Royal Golf Course
10.0 out of 10, Exceptional, (4)
"Beautiful, relaxing, nice people"
Steps from the Ka'anapali Royal Golf Course
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See all available properties in Upcountry Maui
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Upcountry Maui

Hypo-allergenic bedding, in-room safe, blackout drapes
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3007)
"Parking spots are quite small. Luckily we had a small car. "
The price is CA $324
CA $422 total
includes taxes & fees
May 27 - May 28
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2153)
"My friends and I loved our stay at the Aston Villas in Maui! All staff were very helpful and so kind with anything we needed! We had a huge shared balcony on the second floor of the lobby building which we turned out to love! One of our favorite parts was having Castaway Cafe only a few steps away to enjoy some breakfast, mid-day appetizers/lunch, and some delicious lava flows! They have an activities booth right near the pool and Cafe to get anything you need for a fun day on the beach, which...
The price is CA $324
CA $487 total
includes taxes & fees
May 27 - May 28
Aston Maui Kaanapali Villas
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2533)
"Loved staying and celebrating Mother’s Day and my son’s birthday! Couldn’t have asked for a better stay! "
The price is CA $392
CA $1,184 total
includes taxes & fees
Jun 12 - Jun 13
OUTRIGGER Honua Kai Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Upcountry Maui Cottages information

Number of reviews
1,805
Accommodation
22 Cottages
Lowest Price
CA $361
Highest Price
CA $559

Recent Reviews in Upcountry Maui
Expedia verified reviews

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

5/5 Excellent
"My friends and I loved our stay at the Aston Villas in Maui! All staff were very helpful and so kind with anything we needed! We had a huge shared balcony on the second floor of the lobby building which we turned out to love! One of our favorite parts was having Castaway Cafe only a few steps away to enjoy some breakfast, mid-day appetizers/lunch, and some delicious lava flows! They have an activities booth right near the pool and Cafe to get anything you need for a fun day on the beach, which we utilized a lot! One thing I will mention if you’re considering the Aston Villas is housekeeping comes to your room based on a certain schedule, for our room it was every three days. Just a heads up if you decide to come here- had we known we would’ve been more aware of the sand we accidentally dragged in, making our beds, etc.! But all about this hotel was exceptional- we do plan on staying here our next trip around to Maui! Mahalo Maui Kaanapali Villas!!"
A verified traveller stayed at Aston Maui Kaanapali Villas
Posted 2 days ago
Aston Maui Kaanapali Villas