Photo by Claire Houston

Search Cottages in Olowalu

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 27 Cottages in Olowalu with updated reviews, rates, and availability.

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

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

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (136)
"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

10.0 out of 10, Exceptional, (174)
"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!

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!

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!

Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

10.0 out of 10, Exceptional, (190)
"We had a fabulous time and snorkeled every day at one of the best beaches on the island! Terry responded quickly when we didn't have hot water and had the hot water tank replaced as soon as possible. The cottage is very spacious and equipped with many extras in the kitchen. The bathrooms could use some more towels and wash rags, but we were able to wash the existing towels throughout the week because there's a washer/dryer and laundry detergent. There's no AC which bothered some in our party,...
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

Now with optional car add-on

10.0 out of 10, Exceptional, (139)
"Stayed for a week for our honeymoon. Very private. Everything you could want has been provided including warm coats and hats, snorkeling gear, boogie boards, etc. Very gracious hosts who also rented us their car"
Now with optional car add-on

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

Newly Remodelled 4-bedroom cottage in Amazing Kaanapili with ACs

2.0 star property
Newly Remodelled 4-bedroom cottage in Amazing Kaanapili with ACs

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!

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!

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

9.0 out of 10, Wonderful, (22)
"We had a very enjoyable stay at this rental, and it had everything we needed. Great location and well-maintained. It's a little bit outdated, yes, but that didn't bother me at all considering it looked exactly like the listing (even better in my opinion), and was very clean, functional, and still very charming. We really enjoyed eating dinner and watching sunsets on the adorable lanai, and the shared pool in the complex was great! We would definitely rent this place again if we ever return to...
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd

Beach Bungalow with Cruiser Bikes & Pickleball!

9.0 out of 10, Wonderful, (8)
"The property is very clean and we loved having the lanai available with the bbq. Definitely comes in handy with a big family who doesnt want to go out every night. We'd absolutely stay here again."
The price is AED 2,204
AED 4,789 total
includes taxes & fees
13 Jan - 14 January 2025
Beach Bungalow with Cruiser Bikes & Pickleball!

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.

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

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

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

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!
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 Olowalu
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Olowalu

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2647)
"Very nice unit with a layout that served our needs well. A few problems that were not addressed, even though reported. The master bath shower heads did not operate correctly and remained a dribble for showers. My husband says the splitter was broken. There were ants in the laundry room. It would have been nice if the kitchen was better equipped. It was lacking basics and we cook a fair amount. We had to buy items such as cutting board, measuring cups, and a knife that was actually sharp enough...
The price is AED 1,669
AED 3,654 total
includes taxes & fees
10 Jan - 11 January 2025
OUTRIGGER Honua Kai Resort & Spa

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3391)
"Great place to stay at west Maui. Many good snorkeling places. Easy access to beach. Property includes a laundry, grocery just cross street with good poke."
The price is AED 1,465
AED 1,837 total
includes taxes & fees
6 Jan - 7 January 2025
Aston Kaanapali Shores

Royal Kahana Maui by OUTRIGGER

3.0 star property
8.0 out of 10, Very Good, (1322)
"The room was well designed with a great view of the ocean. It had cooking facility and excellent for a linger stay. The rooms have mirrors which helps with light view and makes the room bigger. The rooms also had a washer dryer and together made our stay comfortable and enjoyable"
Royal Kahana Maui by OUTRIGGER
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 Olowalu with Expedia?
We think that a vacation should be easy, so if you’re after cottages in Olowalu at a great price, Expedia delivers. Save money and choose a cheap option far away from the downtown buzz, or splurge on a 5-star cottage to pamper your favorite people.
How can I find cheap cottages in Olowalu?
The easiest way to spot cheap cottages in Olowalu is with Expedia’s convenient filter tool. Tailor your search results by star rating, amenities and budget to nab unbeatable prices in just a few clicks.