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Compare 33 Cottages in Kailua with updated reviews, rates, and availability.

Secluded cottage on Tropical flower farm
Outdoor dining
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, (236)
"The place was wonderful, we really enjoyed our stay! The grounds are gorgeous and filled with so many beautiful plants. Such a sweet place to relax and unwind. A short walk to Hana Farms Roadside stand which is a really great place to grab treats and delicious wood fire pizza. Off the main road so nice and quiet! We loved it!"
Secluded cottage on Tropical flower farm
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, (178)
"The property was everything that was advertised. It was secluded, quiet, clean and everything we needed. Hank was great and made sure what had everything we needed. He never bothered us but was always available.we would definitely recommend this property to anyone. Thanks again, Hank."
ALOHA NOV. DISCOUNT Private, Romantic Cottage, Panoramic Ocean View, Hot Tub
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, (89)
"We had a fantastic stay at Pam’s Treehouse. She made us feel like at home from when we arrived. Pam is passionate about the island and we were amazed by her story. We were amazing by how well stuffed her place is from the water filter to the aftersun and antifog for the snorkel masks. We hope to come back in the future!"
Cozy Maui 'Treehouse' with lovely views and amenities
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Cozy Hana Bay View Cottage with covered lanai, new vinyl decking and siding.
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, (166)
"The location relative to everything we wanted to do and see in Hana was just right. The size of the cottage was just right for the two of us. If I ever get the opportunity to visit Hana again, this is the first cottage I will look for to see if its available!"
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
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)
"Pros: The home was spacious, conveniently located and accurate to the listing photos. We appreciated that the host provided shampoo, conditioner and body wash in the bathroom. The two chilled bottles of water in the fridge were also a nice touch. Cons: There was a surprising amount of noise from the road (cars speeding, blasting music and a few fireworks). The bathroom and bedroom doors were also tricky to close. The floors were dirty when we arrived."
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
Cozy cottage nestled on our 5 acre Organic fruit farm
Food and drink
Cozy cottage nestled on our 5 acre Organic fruit farm
10.0 out of 10, Exceptional, (1)
"This property is absolutely gorgeous and the place had everything we could want for our one night stay. The fresh fruit was such a lovely touch. Wish we had stayed longer!"
Cozy cottage nestled on our 5 acre Organic fruit farm
Great location between Hana Town and Hamoa Beach, private, family-friendly
View from screened-in patio
Great location between Hana Town and Hamoa Beach, private, family-friendly
9.8 out of 10, Exceptional, (214)
"Exactly what we were looking for… so sorry to our neighbor who lost 6 chickens. Hopefully he finds the…"
The price is SAR 1,018
SAR 1,953 total
includes taxes & fees
10 Nov - 11 Nov
Great location between Hana Town and Hamoa Beach, private, family-friendly
Luxury Upcountry retreat with breathtaking views!
Luxury Upcountry retreat with breathtaking views!
10.0 out of 10, Exceptional, (73)
"Excellent location"
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, (149)
"Great host, great location, great property. The open windows allowed for cool sleeping. Seen the whole island during the 12 days there. Thanks John!"
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, (138)
"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, (28)
"This property was fabulous. We were able to easily travel around the island from this cottage and spent many hours on the lanai enjoying the weather. The owners showed the Ohana way of the island. "
1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hamoa Bay Bungalow
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
10.0 out of 10, Exceptional, (64)
"We had an amazing time in Hana! The cabin"
The price is SAR 1,164
SAR 2,049 total
includes taxes & fees
17 Nov - 18 Nov
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
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.
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Luana Cottage
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
9.8 out of 10, Exceptional, (183)
"The property was exactly as described. Beautiful large fruit tree garden property within walking distance to Waianapanapa State Park's black sand beach. Home was very clean and well-stocked. The owner's housekeeper left fresh fruit for us on the day we checked in. Owner was very responsive to questions before our arrival."
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
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
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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Other property types in Kailua

Maui Schooner Resort
Outdoor pool
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (424)
"We loved staying here! Such a great spot with awesome staff!"
Maui Schooner Resort
Sugar Beach Resort
Exterior
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (1018)
"Beautiful property. Great for families. Beautiful sunsets every evening."
Sugar Beach Resort
Maui Beach Vacation Club
Aerial view
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very Good, (694)
"Love. The. Place "
Maui Beach Vacation Club
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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