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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
In two weeks
21 Saf. - 23 Saf.
In one month
7 Rab. I - 9 Rab. I
In two months
4 Rab. II - 6 Rab. II

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

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

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

9.0 out of 10, Wonderful, (31)
"Overall, a very nice accomodation. Close to shops, swap meet, airport, restaurants, etc. Just a good location. Condo is clean and nice. Not in the condo much as we were out seeking adventure. I gave it a 4 out of 5 only because the couch is extremely uncomfortable. Please replace the couch. Mahalo."
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Painting of Maliko Coffee Cabin

Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

10.0 out of 10, Exceptional, (77)
"Beautiful mountaintop view all the way to the ocean, no need for AC with cool tradewinds. The location takes you easily to the Road to Hana or to Haleakala National Park. Super clean and well appointed, charming decor loved it!"
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Evergreen Cottage @ Maui Adventure Villa
Kitchen, Dining Area leading to Screened Lanai

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!
Best views on the Island from every room!

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!

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (75)
"We loved this piece of heaven. The views are incredible. It’s nice to get away from the hustle and bustle of the touristed areas. Upcountry is so pretty and lush. We hiked five minutes away. Got to eat in some really great upcountry restaurants. Found a new beach that is gorgeous, Baby Beach. It’s not for everyone. There is a very windy, steep road of about 15 minutes up from Makawao. We got used to it and it’s pretty. The jungalows’s decor is really pretty and it has all you need. Only downside...
Luxury Upcountry retreat with breathtaking views!
Bamboo Bliss: Ocean Views & Waterfalls Await!
Experience tranquility at the Thai Hale, Maui Eco Retreat, book today

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
Evenings at the bar and patio

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

10.0 out of 10, Exceptional, (176)
"My husband and I thoroughly enjoyed our time at this Maui property and the surrounding area. The apartment offered everything we needed-- a nicely appointed kitchen, comfortable bedroom with sitting area, private swimming pool, laundry facilities and more. It was a short drive to the beaches and to wonderful casual and fine-dining restaurants. Marcello and Alessio were available when we had questions and to offer ideas for activities and dining.We definitely plan to return."
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Living area

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

9.8 out of 10, Exceptional, (17)
"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
View from living room to kitchen

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

10.0 out of 10, Exceptional, (111)
"A clean and comfortable 1-bedroom house, where all appliances, fixtures and functions worked smoothly. Easy walk to a welcoming and interesting downtown, with good restaurants and a nice vibe. Driving to beautiful beaches and intriguing sites was easy. We'd happily stay again."
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Exterior detail

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,...
The price is SAR 1,857
SAR 3,056 total
includes taxes & fees
7 Feb - 8 Feb
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Cottage and pool area with surrounding tropical foliage

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
Welcome to your Private Romantic Cottage in Paradise while enjoying Maui!

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

10.0 out of 10, Exceptional, (182)
"Awesome vacation. Everything was clean and well appointed and organized. Very private. Easy access to everything! "
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Interior

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

9.6 out of 10, Exceptional, (53)
"Very nice place that is great for two people! We stayed there for a week. Pretty much every thing we needed for enjoying our “Beach Time” was provided.And definitely a short walk to get to the beach. The Kitchen was excellent and well stocked, including condiments. Only item worth mentioning is the Small stand up shower and toilet area. If you’re a Large person, this May be looking into. "
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Room

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
Spectacular sunsets viewed from your lanai/patio deck

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
Beautiful coastal decor in this charming cottage.

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.
Property grounds

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
DCP_1439

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

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
Drone view from ocean -- arrow points to cottage roof.

Now with optional car add-on

10.0 out of 10, Exceptional, (141)
"Gail and Jordon are supreme hosts. Their property is perfect for a couples getaway.. They respected our privacy, but made certain we had all we need for comfortable stay.. "
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
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (507)
"Beautiful updated condo. We will return!"
Wailea Ekahi - CoralTree Residence Collection
Wailea Grand Champions - CoralTree Residence Collection
Exterior

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
Maui Beach Vacation Club
Aerial view

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (720)
"Property is very close to the ocean with a nice beach. "
Maui 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.

Frequently asked questions

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