Search Kaupakulua Cottage Rentals from CA $650

  • 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

Browse Select Kaupakulua Cottages

Evergreen Cottage @ Maui Adventure Villa
Property grounds

Evergreen Cottage @ Maui Adventure Villa

9.8 out of 10, Exceptional, (155)
"Great location, great environment, great neighborhood. Nice, quiet and peaceful place to stay after a day of adventures! "
Evergreen Cottage @ Maui Adventure Villa
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, (30)
"The host were very generous with information and helping us. We had a terrific stay"
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Outdoor pool, a heated pool

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (137)
"The property is absolutely incredible. Elaine provided all the information in advance and instructions were all very clear. The place itself is nicely setup. The kitchen had all the things needed for some quick meals and probably more if you wanted to do some additional cooking. For us at least, the proximity to amazing local food kept us largely out of the kitchen. The rooms were nicely setup, and the owners even had a pack'n'play for our toddler which was great. The pool was of course the...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Outdoor dining

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

10.0 out of 10, Exceptional, (175)
"Absolutely had a great experience staying there."
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
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, (141)
"Cozy, clean, absolutely priceless view, easy access to ocean and poised for sunset watching indoors and out. Amenities were perfect and everything we needed was a short drive away (other beaches, amazing food, shopping, local life, food trucks, and community. "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
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, (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!
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage

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

10.0 out of 10, Exceptional, (181)
"We both felt so comfortable and at home in this lovely open concept accommodation. The owner and manager were very helpful. They both offered hand picked oranges, tangerines, bananas and lemons that grew on the property. The bed was very comfortable and the kitchen was well appointed with everything one could need. We will definitely be back. "
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage
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, (140)
"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
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Outdoor dining

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

10.0 out of 10, Exceptional, (67)
"The cottage is quite cozy and comfortable"
The price is CA $650
CA $1,098 total
includes taxes & fees
Jan 26 - Jan 27
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Heaven on Earth in Upcountry Maui
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Pool

Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

10.0 out of 10, Exceptional, (76)
"The coffee cabin was perfect for our short stay in upcountry Maui. The location was amazing & peaceful, and it was the perfect size for 4 people. Sydney is a great host, and the included local fruit/coffee, personal tour & access to the swimming holes were a wonderful addition to our stay. I highly recommend Sydney’s cabin to anyone looking to stay in upcountry Maui!"
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Cozy Maui 'Treehouse' with lovely views and amenities
Exterior

Cozy Maui 'Treehouse' with lovely views and amenities

10.0 out of 10, Exceptional, (91)
"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
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Outdoor dining

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

9.4 out of 10, Exceptional, (31)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
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, (99)
"Perfect place to stay when planning on windsurfing Hookipa. "
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Luxury Upcountry retreat with breathtaking views!
Outdoor pool

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!
Indulge, just steps to pristine beaches, restaurants & shopping.
Sun loungers, beach towels

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.
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (84)
"Everthing was as advertised. Robert answered all our questions. The property was secluded. Eveything we needed for our visits to the local community were available. "
Private, Serene & Cute Cottage. Ocean Views & A/C. Near Hana Hwy.
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Beach nearby

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

10.0 out of 10, Exceptional, (110)
"We had a great time staying in Jacque's cottage on the North Shore, far from the Maui crowds. Pa'ia is charming and funky, and we loved that all the local restaurants and shops were just a short walk away. It's ideal if you are looking for something a bit different from the typical Hawaiian tourist experience, as we were. It's also a great jumping-off point for Haleakala, the Road to Hana, and upcountry Maui. The owners are friendly and communicate well. On our first day, a light bulb burned...
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Sun loungers, beach towels

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
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
Property grounds

Ocean View 1 BR Cottage on Oceanfront Property. Permitted

10.0 out of 10, Exceptional, (70)
"Lovley cottage in a great location. Had a great time staying there."
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
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

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (709)
"The place was very good for me and my family, it was very close to every were, the beach is just on the other side of the resort"
Maui Beach Vacation Club
Wailea Grand Champions - CoralTree Residence Collection
2 outdoor pools

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (684)
"Considering how much less it cost than nearby non-resort hotels, I was astounded at how nice this property was. The washer and dryer and multiple bedrooms/bathrooms were excellent, and I was extremely impressed by the cleanliness and condition of the unit. No odors or stickiness or any of the other issues that tend to occur at properties with kitchens. Check-in was easy and the walk to resorts and shops was fine (although there's a section without a sidewalk and the hills might be a bit much for...
Wailea Grand Champions - CoralTree Residence Collection
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1034)
"The entry key code wouldnt work, tried several times, took the main help line forever to pick-up, the on-site staff stayed but left even though i hadnt gotten in the room, the chatbot got back to me late in the evening. Finally, was able to get a code to work. Nevertheless a bit nerve racking. Otherwise, everything else was very nice. Liked it was on main level, made it easy to access beach, the rooms were nice so you couldnt hear neighbors through the walls and there were ample parking. "
Sugar Beach Resort
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.