Photo by Claire Houston

Search Olowalu Cottage Rentals from CA $649

  • 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 Olowalu Cottages

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
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
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, (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
Outdoor dining

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

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

10.0 out of 10, Exceptional, (191)
"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
On the beach, sun loungers, beach towels

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
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 $649
CA $1,095 total
includes taxes & fees
Jan 26 - Jan 27, 2025
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Newly Remodelled 4-bedroom cottage in Amazing Kaanapili with ACs
Beach

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
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
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!
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
Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd
Sun loungers, beach towels

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!
Fridge, microwave, oven, stovetop

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 CA $865
CA $1,855 total
includes taxes & fees
Jan 13 - Jan 14, 2025
Beach Bungalow with Cruiser Bikes & Pickleball!
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.
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
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Interior

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
Sign in
Sign up, it's free

Other property types in Olowalu

OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2651)
"This place was absolutely amazing! Very clean, friendly staff, spacious and quiet but lively at the same time, amazing balconies with unbelievable views and an overall perfect place to get away! The outdoor areas were clean and inviting- 3 pools and 5 hot tubs. We all loved the food trucks that were within walking distance. Parking was close and easy. Would recommend this place to everyone! It had a condo but resort feel which was super nice! "
The price is CA $655
CA $1,434 total
includes taxes & fees
Jan 11 - Jan 12, 2025
OUTRIGGER Honua Kai Resort & Spa
Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3394)
"We were a party of 12, with ages varying from 2-60. We shared two suites, which they helped us be right next to each other. The property was a little older and showing its age but rooms were spacious. The suites were well appointed, with well stocked kitchens for cooking and lots of storage space. Free activities were great and kept us busy, including their Christmas party, stocking votes, ukulele lessons and lei making ($). Pools were great for all ages. Being right on the beach was perfect,...
The price is CA $575
CA $721 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Aston Kaanapali Shores
Royal Kahana Maui by OUTRIGGER
Condo, 2 Bedroom, Oceanfront (Unit 410, 2Bath) | Terrace/patio

Royal Kahana Maui by OUTRIGGER

3.0 star property
8.0 out of 10, Very good, (1323)
"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.