Kaanapali Hillside Cottages

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Cottages in Kaanapali Hillside

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

With a stay at this cottage, you'll be centrally located in Wailuku, just a 4-minute walk from Iao Theater and 9 minutes by foot from Kaʻahumanu Church.

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

When you stay at this cottage in Kaanapali, you'll be next to a golf course, within a 5-minute drive of Kaanapali Beach and Whalers Village.

Now with optional car add-on

Located in Wailuku, this cottage is on the beach, within a 5-minute walk of Coral Beach and Waiehu Beach.

Newly Remodelled 4-bedroom cottage in Amazing Kaanapili with ACs

With a stay at this cottage in Kaanapali, you'll be a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.

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

When you a stay at this cottage in Kihei, you'll be on the beach, within a 5-minute walk of Waipuilani Park and Waipuilani Beach.

Maui Mango Cottage 🌺 Stellar Lanai 🌺 Private Hidden Gem 🌺 Family Friendly 3bd

When you stay at this cottage in Kaanapali, you'll be by the sea, within a 5-minute drive of Kaanapali Beach and Whalers Village.

Beach Bungalow with Cruiser Bikes & Pickleball!

$849

includes taxes & fees

$730 per night

Nov 26 - Nov 27

With a stay at this cottage in Kaanapali, you'll be a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.

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

With a stay at this cottage, you'll be centrally located in Wailuku, just a 4-minute walk from Iao Theater and 9 minutes by foot from Kaʻahumanu Church.

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

A stay at this cottage places you in the heart of Wailuku, within a 15-minute walk of Kaʻahumanu Church and Bailey House Museum.

Kihei - Tropical Cottage Across from the Beach - PERMIT # STKM 2015/0003

Located in Kihei, this cottage is by the sea, within a 5-minute walk of Maalaea Bay Beaches and Sugar Beach.

PRIVATE COTTAGE/GAZEBO WITH HOTTUB

With a stay at this cottage in Wailuku (Wailuku Heights), you'll be steps from West Maui Mountains and 11 minutes by foot from Bailey House Museum.

A GEM IN THE MIDDLE OF THE PACIFIC - OCEAN VIEW - KAANAPALI

With a stay at this cottage, you'll be centrally located in Kaanapali, within a 5-minute drive of Kaanapali Beach and Whalers Village.

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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.