Search Upcountry Maui Cottage Rentals from CA $391

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Browse Select Upcountry Maui Cottages

Secluded cottage on Tropical flower farm
Outdoor dining
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, (226)
"We loved our stay here. The place was very clean, and the scenery was stunning. It was a very relaxing and enjoyable place to stay. There were issues on the island with power going out due to a fallen tree in the forest, but the owners were very responsive to texts and even drove out to give us lanterns in case there was another outage. I highly recommend staying here!"
The price is CA $402
CA $761 total
includes taxes & fees
Jun 9 - Jun 10
Secluded cottage on Tropical flower farm
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Beach
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, (161)
"Very nice no complaints would book again"
The price is CA $402
CA $751 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Evergreen Cottage @ Maui Adventure Villa.
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.
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Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
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!
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
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
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Pool
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, (130)
"Beautiful property in Wailea. We enjoyed the pool all day and Elaine was so sweet. Will stay here again."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
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
Cozy Maui 'Treehouse' with lovely views and amenities
Exterior
Cozy Maui 'Treehouse' with lovely views and amenities
10.0 out of 10, Exceptional, (88)
"I loved everything about my stay at the Treehouse. It was such a wonderful, calm place to stay but still had everthing I needed (and want) in a vacation stay (including a laundry hamper and a full legnth mirror which are just so nice to have, but many places don't include). The kitchen and bathroom are perfectly stocked with everything you might need. The bed is so comfortable and the bonus of the AC in the bedroom let me get a great night's sleep every night. The neighborhood was very quiet,...
Cozy Maui 'Treehouse' with lovely views and amenities
SUMMER DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
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
Now with optional car add-on
On the beach, sun loungers, beach towels
Now with optional car add-on
10.0 out of 10, Exceptional, (136)
"Great setup! Very good location for seeing all of Maui. Very well equipped. Owner very helpful. Unobstructed view of sunrise over the Pacific."
Now with optional car add-on
Great location between Hana Town and Hamoa Beach, private, family-friendly
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 $391
CA $737 total
includes taxes & fees
Jun 11 - Jun 12
Great location between Hana Town and Hamoa Beach, private, family-friendly
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
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!
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
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
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
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
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
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
3BR Beach Bungalow with 1967 International Scout!
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 $422
CA $1,103 total
includes taxes & fees
Jun 9 - Jun 10
3BR Beach Bungalow with 1967 International Scout!
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Fridge, microwave, oven, stovetop
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
9.0 out of 10, Wonderful, (23)
"perfect"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
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!
A unique dolphin cabin in Kaanapali!
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!
Steps from the Ka'anapali Royal Golf Course
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

Aston Kaanapali Shores
Hypo-allergenic bedding, in-room safe, blackout drapes
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3026)
"Quiet! Safe! Grocery nearby!"
The price is CA $361
CA $466 total
includes taxes & fees
Jun 5 - Jun 6
Aston Kaanapali Shores
Aston Maui Kaanapali Villas
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2166)
"This is more of a quiet area and has way more plants than the other hotels which made me feel more relaxed. We only called the hotel twice and maintenance came super fast and fixed everything. Loved how there is 2 pools, one big main one and one smaller with a hot tub. There’s a cafe on the beach side that is 10000/10 best spot to eat. I would def recommend, the room was super spacious as well, very private balcony "
The price is CA $324
CA $486 total
includes taxes & fees
Jun 5 - Jun 6
Aston Maui Kaanapali Villas
Kahana Beach Vacation Club
Standard Room, 1 Bedroom | Living area
Kahana Beach Vacation Club
3.0 star property
8.4 out of 10, Very good, (546)
"My daughter and I had an amazing time here celebrating her master's degree. We booked a 1 BR and are so glad we did. The condo was HUGE. The bedroom was x-large, as well as the living are. Both with a large TV in each. We also had two full bathrooms (one with a tub and the other with a full size shower). The kitchen had everything you'd need to cook meals. We were pleasantly surprised with all the cooking tools and gadgets. Being recently renovated, everything was brand new. The only thing...
Kahana Beach Vacation Club
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
1,810
Accommodation
22 Cottages
Lowest Price
CA $391
Highest Price
CA $422

Recent Reviews in Upcountry Maui
Expedia verified reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

5/5 Excellent
"Great property for the price. Loved everything about it but what really stands out is the friendliness and customer service was top notch. Will definitely go there again "
A verified traveller stayed at OUTRIGGER Kaanapali Beach Resort
Posted 5 hours ago
OUTRIGGER Kaanapali Beach Resort