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Aug 8 - Aug 10
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Aug 29 - Aug 31
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Browse Select Olowalu Cottages

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
Relax by the serene pool surrounded by lush greenery and a fence.

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

10.0 out of 10, Exceptional, (194)
"Could not have been better. Cottage is a little jewel. Carrie, the host,is an amazing, kind and helpful person, Highly recommend staying at the cottage."
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
Enjoy a serene beachside retreat with a palm tree, gentle slope, and calm sea.

Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!

10.0 out of 10, Exceptional, (152)
"Just the right amount of everything. Comfortable tasteful decor with the benefit of the beach just steps away. Beautiful location and easy access to hiking, snorkeling and outdoor exploration. Enjoyed every second of our week there. "
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Relax by the pool surrounded by lush greenery and comfortable seating options.

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (146)
"We had a wonderful stay at Elaine's cottage. The location and property were perfect for us. Thanks for a fantastic week. "
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Relax in a serene outdoor space surrounded by lush greenery and a pergola.

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

10.0 out of 10, Exceptional, (183)
"Great location-convenient to beaches, restaurants but also very private! Villa set in beautifully landscaped yard. Lovely pool for daytime use and when lit up at night."
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Enjoy al fresco dining on this outdoor deck with a pergola, overlooking a residential area and a clear sky.

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

9.2 out of 10, Wonderful, (34)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
Enjoy serene beachfront views and tranquil surroundings.

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

10.0 out of 10, Exceptional, (198)
"Relaxing getaway with great views. Great Host"
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Enjoy meals in this kitchen with a window offering a view of lush greenery.

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

9.4 out of 10, Exceptional, (26)
"Clean, convenient, comfortable! We stayed for a few night while visiting the islands. Highly recommend and may stay here again when visiting local family!"
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Enjoy al fresco dining and relaxation in this beautifully appointed patio, featuring a dining table, comfortable seating, and a barbecue grill.

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

10.0 out of 10, Exceptional, (71)
"This charming cottage is a marvel of great design, surrounded by a beautiful garden. We enjoyed walking through the friendly neighborhood on our way to town. The owners are skilled, organized inn keepers. All contributed to a wonderful week on Maui."
The price is CA $483
CA $871 total
includes taxes & fees
Aug 23 - Aug 24
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Beach Bungalow w/ Cruiser Bikes & Pickleball!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

Beach Bungalow w/ Cruiser Bikes & Pickleball!

9.2 out of 10, Wonderful, (10)
"We often had the pool to ourselves, occasionally sharing it with at most one other family. The location is convenient and it was easy to get to many different beaches. One thing to be aware of: the loft ceiling is quite low and the space there is tight. The extra twin rollout bed is at the floor level. "
The price is CA $379
CA $1,203 total
includes taxes & fees
Aug 16 - Aug 17
Beach Bungalow w/ Cruiser Bikes & Pickleball!
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Enjoy a serene beach experience with palm trees and a stunning mountain backdrop.

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

9.6 out of 10, Exceptional, (60)
"Great little cottage Simple and convenient for my needs Would definitely stay here again!"
Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Enter a cozy room with a blue door, featuring a comfortable chair and a small table.

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

9.8 out of 10, Exceptional, (13)
"Super cute little stay for 2 people! You’re close to a lot of local spots and about 20 min from the touristy spots (which we did not mind). The hosts were great! They had a cute little basket with eggs, snacks and banana bread when we got there. They even kept us in the loop for local events and we even got to check one out while we were there! There are tons of roosters that you will hear every morning but that’s just Hawaii for ya! Everything was perfect! Would definitely recommend ☺️"
Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!
Cozy Maui 'Treehouse' with lovely views and amenities
Enjoy the serene views from the upper balcony, which offers a staircase leading to a peaceful outdoor space.

Cozy Maui 'Treehouse' with lovely views and amenities

9.8 out of 10, Exceptional, (94)
"It had everything we needed. Close to the beaches, restaurants, shopping, and main roads. Comfortable beds, and a nice kitchen. Pamela is very helpful. We had very good time."
Cozy Maui 'Treehouse' with lovely views and amenities
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Enjoy meals in this kitchen with a central island, dining table for two, and a view of the lush garden.

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

9.2 out of 10, Wonderful, (36)
"The neighborhood was a nice change from some of the more touristy areas of the island."
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Heaven on Earth in Upcountry Maui
Relax in this inviting room with a large bed, patterned bedspread, and scenic views from the balcony.

Heaven on Earth in Upcountry Maui

10.0 out of 10, Exceptional, (96)
"We had an amazing stay in upcountry Maui. The cottage was super clean, well-stocked and exactly as described. We loved the location, a very peaceful, rural countryside vibe. Loved the cats, we could see deer, sheep and of course chickens! If you want a quiet peaceful stay away from the crowds I would highly recommend."
Heaven on Earth in Upcountry Maui
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Enjoy a serene beach experience with calm ocean waters and a scenic shoreline.

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

10.0 out of 10, Exceptional, (116)
"Quiet, comfortable, and a short walk to town. No complaints."
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
Relax on the lawn with ocean views, surrounded by palm trees and picnic tables.

Ocean View 1 BR Cottage on Oceanfront Property. Permitted

10.0 out of 10, Exceptional, (73)
"Beautiful location wonderful host!! "
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Enjoy a serene beach experience with calm ocean waters and scenic views of the surrounding trees and vegetation.

Plantation Style cottage short walk to beach and town Permit STPH2013/0004

9.8 out of 10, Exceptional, (108)
"Great location for adventuring all over Maui! Host was very responsive during our stay. Property was clean and has lots of extras that made our stay nicer (dishes, beach chairs, boogie boards, privacy fence, AC in each room etc)."
Plantation Style cottage short walk to beach and town Permit STPH2013/0004
Now with optional car add-on
Guests can enjoy ocean views from the deck, surrounded by lush greenery and a white railing.

Now with optional car add-on

10.0 out of 10, Exceptional, (143)
"Great quiet oceanfront location. Great cottage. Super helpful hosts. "
Now with optional car add-on
Cute Kihei Cottage - Large Outdoor Deck
Relax on the patio with a sofa, chairs, and fire pit, surrounded by a charming white picket fence and a cozy building with a seating area.

Cute Kihei Cottage - Large Outdoor Deck

Cute Kihei Cottage - Large Outdoor Deck
Indulge, just steps to pristine beaches, restaurants & shopping.
Guests can enjoy a serene ocean view from this beachfront location.

Indulge, just steps to pristine beaches, restaurants & shopping.

10.0 out of 10, Exceptional, (22)
"We loved everything about our stay. The place was adorable with lots of little touches. The patio was amazing and we enjoyed sitting and reading. The location was perfect for everything. Seriously great place!"
Indulge, just steps to pristine beaches, restaurants & shopping.
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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Top Olowalu Hotel Reviews

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"Everything was top rate! Can’t wait to go back."
Anonymous traveller 2-night trip
Posted 22 hours ago
Four Seasons Resort Maui at Wailea