Search Cottages in Kaupakulua

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 32 Cottages in Kaupakulua with updated reviews, rates, and availability.

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, (173)
"Ohana is a very important belief in Hawaii. At Villa Paola, they go even further and embrace you into their Famiglia. First of all, words cannot describe the beauty of this home. The moment you enter the driveway, the lush greenery envelopes you and you literally feel like you have found paradise. You enter the home to find everything you want and more. The house is incredibly clean and welcoming. The bed is so comfortable, and the bathroom exquisite. You could lose yourself in the gallery...
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
Welcome to your Private Romantic Cottage in Paradise while enjoying Maui!

ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub

10.0 out of 10, Exceptional, (179)
"We absolutely LOVED staying here. When we arrived our breath was taken away - not only from the sunset view, but from the cleanliness and attention to detail taken for the cottage. Everything was beautiful - from the fresh fruit and snacks greeting us on arrival, to the immaculate furnishings and build of the cottage. The photos definitely don't to it justice. It was easily our favourite accommodation and location we stayed in. Hank, your host, is incredibly accommodating and quick to respond to...
ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
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, (135)
"Love staying at this beautiful cottage and being so close to the beach and great restaurants and shopping. Truly the best way to experience this side of the island of Maui. Elaine is a wonderful host and very helpful. The pool is my favorite experience here can't wait to return."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
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, (90)
"Enjoyed staying in a quiet peaceful neighborhood within walking distant to the beach. Having our own space and deck was relaxing after a busy day exploring the island."
Cozy Maui 'Treehouse' with lovely views and amenities
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!
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, (99)
"Perfect place to stay when planning on windsurfing Hookipa. "
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
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, (107)
"Clean and very easy wall to town. Would definitely stay here again."
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
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, (30)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Luxury Upcountry retreat with breathtaking views!

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (74)
"Stayed here a few years ago, and we loved our return stay. Very peaceful in a beautiful setting with incredible views, this is a unique and fantastic way to experience Maui. Great, clear and concise communications with David. We look forward to returning…mahalo!"
Luxury Upcountry retreat with breathtaking views!
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, (138)
"The convenience, the communication with the owners, The little extra touches, and the ease of access and accommodations were superb. We would definitely stay there again."
Now with optional car add-on
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, (93)
"Star Lookout is located in upland Maui - the cottage has spectacular views of both east and west maui and amazing views of the night sky - so wonderful we deliberately got up in the middle of the night to see it "
Heaven on Earth in Upcountry Maui
Evergreen Cottage @ Maui Adventure Villa
Kitchen, Dining Area leading to Screened Lanai

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (150)
"Loved our time here. Good location to everything on the island. "
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, (139)
"We had a wonderful time in this private little cottage. Good location, with shops and restaurants nearby. Great ocean views. Btw, the Maui Aquarium is a great stop for an afternoon and lunch in the outdoor restaurant was very good. "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
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, (29)
"Well cared for home and close to everything in old town!! We enjoyed a comfortable stay at this cozy home!"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
Palm Cottage - a cute cottage in a serene setting with coastal ocean views.

Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.

10.0 out of 10, Exceptional, (83)
"Beautiful & peaceful location"
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
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
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, (66)
"The cottage is quite cozy and comfortable"
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
Plantation style cottage, living area is upstairs, covered deck.

Ocean View 1 BR Cottage on Oceanfront Property. Permitted

10.0 out of 10, Exceptional, (69)
"Great "
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Room

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

9.6 out of 10, Exceptional, (10)
"Comfortable and clean.Very quiet.All kitchen and bathroom supplies were provided. Snacks and fresh eggs and a welcome letter were a wonderful gift. We will be back in 2 years "
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
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.
Don't see what you're looking for?
See all available properties in Kaupakulua
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Kaupakulua

Aston Maui Hill
Aerial view

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (752)
"The apartment was beautifully decorated. Very clean. The grounds lovely, and a short distance to a strip of beach. The pool was closed for renovation, which was disappointing, as it looked beautiful and to be a respectable size. Monday night happy hour with all residents was a wonderful. treat. Drinks and food! We were the youngest in the crowd at 30's and 50's.The beds were comfortable. The kitchen has no oven and was not well equipped; we figured it out. Truly a nice place. This is located at...
Aston Maui Hill
Maui Beach Vacation Club
Aerial view

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (699)
"Great!"
Maui Beach Vacation Club
Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (494)
"Beautiful condo"
Wailea Ekahi - CoralTree Residence Collection
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

Why book your cottage in Kaupakulua with Expedia?
Expedia has some superb cottages in Kaupakulua, so get ready for a memorable vacation close to nature. If you have a budget in mind, select how much you’d like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with free WiFi or a kitchen. We’ll help you find a suitable place whatever your plans or bank balance.
How can I find cheap cottages in Kaupakulua?
With Expedia’s user-friendly filter tool, comparing cheap cottages in Kaupakulua is a cinch. To view accommodations that’ll make your bank balance smile, fine-tune your search results by star rating, budget and amenities.