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Compare 31 Cottages in Kaupakulua with updated reviews, rates, and availability.

1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

9.0 out of 10, Wonderful, (32)
"I was traveling for work and the house was convenient for my meetings and very spacious to work in and rest in. I found my stay lovely. "
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

10.0 out of 10, Exceptional, (79)
"Lovely single room home set in elevated tropical surroundings with terrific long view to ocean. We highly recommend the location and property tour by owner"
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (156)
"Beautiful property "
Evergreen Cottage @ Maui Adventure Villa

Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!

10.0 out of 10, Exceptional, (142)
"This unit works out perfect for my husband and I is incredibly comfortable and pleasant. Working with the manager is very easy and she is very accommodating. I’ve already booked for next year!"
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (76)
"Everything about this place is magical. The views amazing. On the side of Haleakala looking towards West Maui mts! Lots of things to do on that side of island and great restaurants. Hosts were awesome. "
Luxury Upcountry retreat with breathtaking views!

Bamboo Bliss: Ocean Views & Waterfalls Await!

Bamboo Bliss: Ocean Views & Waterfalls Await!

Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

10.0 out of 10, Exceptional, (178)
"We enjoyed the large outdoor space and private pool. The owners are very responsive and provide drinking water on tap. Lots of great artwork throughout the space. The outdoor bar area is especially nice. The pool is not heated and is very deep so can be a little brisk. Recommend mapping the address on your phone rather than looking at the location in the listing on the VRBO site as the map there is not accurate.. "
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

9.8 out of 10, Exceptional, (18)
"This place was a great option for staying on Maui and being able to get to just about everywhere. It’s a great place to begin a trip down the Road to Hana, and there are a lot of good places to eat in the city. Highly suggest trying JJ’s Tacos food truck just blocks away. The bed was comfortable and the AC worked very well for a good nights sleep. "
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004

10.0 out of 10, Exceptional, (112)
"Quiet, comfortable, and a short walk to town. No complaints."
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

10.0 out of 10, Exceptional, (69)
"My wife and I have stayed at many different vacation rentals over the years, and this property is the best, pound for pound, that we have stayed in.It packs a real punch into its 1Bed/1Bath footprint. Hot tub, outdoor shower, two separate outdoor seating areas, in unit laundry, smart TVs, high quality linens, a luxury shower, and more! And that's just the physical features. The hosts Jenni and Dave think of literally everything they can to make your stay wonderful. Whether it's a welcome gift,...
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (138)
"Miss Elaine’s place was fantastic! We had everything we needed. The place was clean, not too far from the beach, and it was close to stores and restaurants. We rented a car and only had to fuel up 2 times during the 2 weeks we were there. The pool was amazing, our daughter (5 years old) had so much fun hanging out at the pool. It was nice on days when we did not want to do too much. Beach days were awesome because she had 2 coolers, 3 beach chairs, 2 boogie boards and plenty of towels available...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage

10.0 out of 10, Exceptional, (183)
"We had a wonderful stay at this peaceful and beautiful house. The entire process was smooth, and the house is well furnished. We’ve come to really enjoy the Haiku area It’s rural enough for quiet but within 15 minutes to Kahului and several small towns, and quite handy for day trips to Hana or Haleakalā. If you want an escape from the tourist areas of Maui, this is a wonderful option. "
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

9.6 out of 10, Exceptional, (55)
"This unit is very well equipped with everything you need. The space is comfortable and spacious for two. Has a nice private patio area. It is easy to get to from the airport by car, has grocery options within a few miles, and is within walking distance of the beach and several restaurants. The owner is very responsive to needs. We'd be happy to stay her again if in Maui."
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

9.8 out of 10, Exceptional, (11)
"This was a great place to stay. We loved coming home to it. The owners were very nice. The little grey cat was so welcoming and we appreciated his company. Our only "complaint" would be the beds. They are a tad uncomfortable. But we all survived unscathed. Thanks Jon and Jody"
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

Cozy Maui 'Treehouse' with lovely views and amenities

10.0 out of 10, Exceptional, (91)
"Peaceful property in a locals neighborhood. Wake up to birdsong. Close to all amenities, including the beach, by foot and by car, which was very nice. Enjoyed our stay. Mahalo!"
Cozy Maui 'Treehouse' with lovely views and amenities

Plantation Style cottage short walk to beach and town Permit STPH2013/0004

9.8 out of 10, Exceptional, (100)
"Perfect place to stay when planning on windsurfing Hookipa. "
Plantation Style cottage short walk to beach and town Permit STPH2013/0004

Indulge, just steps to pristine beaches, restaurants & shopping.

10.0 out of 10, Exceptional, (20)
"Very well appointed and located, near restaurants and within a short drive (10-15 mins) of great beaches. Highly recommend."
Indulge, just steps to pristine beaches, restaurants & shopping.

Heaven on Earth in Upcountry Maui

10.0 out of 10, Exceptional, (94)
"We really enjoyed our stay here in Kula. The cottage was absolutely perfect with stunning views of the ocean and mountains. Thanks again to the host Zsuzsanna for welcoming us and making our stay very comfortable. Hope to see you again sometime soon "
Heaven on Earth in Upcountry Maui

Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining

9.4 out of 10, Exceptional, (31)
"Second year we have stayed here. Very quiet on dead end street in Maui Meadows. Beautiful view. Really no issues at all. Will stay here again next year when we return to Maui!"
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining

Now with optional car add-on

10.0 out of 10, Exceptional, (141)
"Great quiet oceanfront location. Great cottage. Super helpful hosts. "
Now with optional car add-on
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.
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Other property types in Kaupakulua

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (510)
"Coral Tree Residence Collection was awesome to work with. "
Wailea Ekahi - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (688)
"Great stay. Great customer services. Property was perfect for our 9 day stay!"
Wailea Grand Champions - CoralTree Residence Collection

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very Good, (2208)
"Great location, close to shopping, food, beaches, restaurants, grocery stores. New floor installation next door for 5 days, was bit noisy. Sofa bed was uncomfortable. Had AC, ceiling fans, 2 bathrooms. Let us stay late due to pending storm, very accommodating. Grounds are very beautiful and well maintained. Swimming pool great. Friendly staff. "
Castle Kama'ole Sands
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.

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