Kaanapali Hillside Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Kaanapali Hillside hotels

Lobby
Maui Seaside Hotel

Maui Seaside Hotel

Maui Seaside Hotel
3.0 star property
Kahului
9.0 out of 10, Wonderful, (1190)
"Great accommodations. Beautiful location and nice staff "
United States
Kyle
The price is €251
includes taxes & fees
13 Jan - 14 Jan 2026
Maui Seaside Hotel
View from room
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows
4.0 star property
Lahaina
8.4 out of 10, Very good, (1585)
"Everyone was friendly and location was great "
United States
Ramon Garibay
The price is €230
includes taxes & fees
17 Dec - 18 Dec
Royal Lahaina Resort & Bungalows
Terrace/patio
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali
4.5 star property
Lahaina
9.0 out of 10, Wonderful, (1011)
"We enjoyed every minute of our stay, this property is beautiful and the beach is beautiful as well. "
United States
Ann
The price is €536
includes taxes & fees
9 Jan - 10 Jan 2026
The Westin Maui Resort & Spa, Ka'anapali
Outdoor pool, open 8:00 AM to 8:00 PM, pool cabanas (surcharge)
Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1009)
"staff are very friendly and easy to deal with and the hotel is clean "
United States
Edel Nuqui
The price is €340
includes taxes & fees
19 Dec - 20 Dec
Sheraton Maui Resort & Spa
Exterior
Maui Beach Hotel

Maui Beach Hotel

Maui Beach Hotel
3.0 star property
Kahului
7.2 out of 10, Good, (1115)
"Awesome staff awesome view couldn’t ask for more from this quaint cute hotel vibe!"
United States
Lindsey
The price is €215
includes taxes & fees
23 Dec - 24 Dec
Maui Beach Hotel
View from property
The Mauian - Boutique Beach Studios on Napili Bay

The Mauian - Boutique Beach Studios on Napili Bay

The Mauian - Boutique Beach Studios on Napili Bay
3.0 star property
Lahaina
9.2 out of 10, Wonderful, (979)
"Great staff. Intimate hotel. "
United States
Autumn Rosa
The Mauian - Boutique Beach Studios on Napili Bay
Outdoor pool, open 8:00 AM to 9:00 PM, pool loungers
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort
3.5 star property
Lahaina
9.2 out of 10, Wonderful, (1517)
"Great spot, ideal location and one of the best beaches on island"
United States
Joseph
The price is €359
includes taxes & fees
14 Jan - 15 Jan 2026
OUTRIGGER Kaanapali Beach Resort
Sun deck
Kohea Kai Hotel Maui

Kohea Kai Hotel Maui

Kohea Kai Hotel Maui
3.0 star property
North Kihei
8.6 out of 10, Excellent, (874)
"Clean, simple and satisfied all our needs for a beautiful stay in Maui! Right on the beach, and close drive to plenty of other nearby beautiful beaches. "
United States
Idan
The price is €200
includes taxes & fees
19 Dec - 20 Dec
Kohea Kai Hotel Maui
On the beach
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas
4.0 star property
North Kihei
9.2 out of 10, Wonderful, (219)
"Clean and well equipped room, helpful and friendly staff. "
Canada
Asel
The price is €393
includes taxes & fees
14 Jan - 15 Jan 2026
Hilton Grand Vacations Club Maui Bay Villas
Outdoor pool, pool umbrellas, pool loungers
Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport
4.0 star property
Kahului
9.0 out of 10, Wonderful, (1000)
"Clean room,helpful and pleasant staff, good food in the Bistro, quiet, comfortable room."
United States
Deborah
The price is €366
includes taxes & fees
19 Dec - 20 Dec
Courtyard Maui Kahului Airport
Exterior
Yonegan Central Maui Getaways

Yonegan Central Maui Getaways

Yonegan Central Maui Getaways
2.0 star property
Wailuku
8.4 out of 10, Very good, (41)
"Great price, location & amenities"
United States
Borys
The price is €143
includes taxes & fees
21 Dec - 22 Dec
Yonegan Central Maui Getaways
Beachfront Two Bedrooms
Napili Sunset on the Beach

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647)
"Location was excellent"
United States
Polly
The price is €282
includes taxes & fees
17 Dec - 18 Dec
Napili Sunset on the Beach
3 outdoor pools, pool cabanas (surcharge), pool loungers
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.0 out of 10, Wonderful, (1002)
"Amenities were great. Wonderful stay!"
United States
Joseph
The price is €758
includes taxes & fees
17 Dec - 18 Dec
The Ritz-Carlton Maui, Kapalua
On the beach
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1712)
"Excellent stay. "
United States
casey william
The price is €370
includes taxes & fees
21 Dec - 22 Dec
Napili Shores Maui by OUTRIGGER
Exterior
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui
4.0 star property
Kaanapali
9.0 out of 10, Wonderful, (1004)
"Great stay, close to everything and away from the crowd."
United States
Muyi
The price is €310
includes taxes & fees
18 Dec - 19 Dec
Hilton Vacation Club Ka'anapali Beach Maui
6 outdoor pools, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (1004)
"Loved it can’t wait to go back "
United States
Tiffany
The price is €607
includes taxes & fees
9 Jan - 10 Jan 2026
Hyatt Regency Maui Resort & Spa
2 outdoor pools
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2516)
"We enjoyed the property "
United States
Therese
The price is €431
includes taxes & fees
17 Dec - 18 Dec
Aston Maui Kaanapali Villas
Interior
The Historic Wailuku Inn

The Historic Wailuku Inn

The Historic Wailuku Inn
3.0 star property
Wailuku
9.0 out of 10, Wonderful, (34)
"Lovely historical house, beautiful garden "
United States
Debra
The Historic Wailuku Inn
Suite, Multiple Beds, Garden View (2 Baths) | Garden view
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (316)
"great time, great resort, helpful staff"
Canada
Prableen
The price is €647
includes taxes & fees
15 Jan - 16 Jan 2026
The Whaler Resort Kaanapali Beach
Property grounds
The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1126)
"Perfect stay"
United States
hao
The price is €449
includes taxes & fees
22 Dec - 23 Dec
The Westin Ka'anapali Ocean Resort Villas
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kaanapali Hillside Hotel Reviews

The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent
"The view from the room was amazing. Full ocean view"
Janet 4-night trip
Posted 1 day ago
The Westin Maui Resort & Spa, Ka'anapali

More cheap stays in Kaanapali Hillside

Yonegan Central Maui Getaways

Yonegan Central Maui Getaways

197 North Market Street Wailuku HI
The price is €143 per night from 21 Dec to 22 Dec
€143
21 Dec - 22 Dec
includes taxes & fees
8.2/10 Very Good! (40 reviews)

Frequently asked questions

What's the best place for a stay in Kaanapali Hillside?
The Westin Maui Resort & Spa, Ka'anapali, located 1.1 mi (1.8 km) from the heart of Kaanapali Hillside, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Royal Lahaina Resort & Bungalows and OUTRIGGER Kaanapali Beach Resort. See all available top hotels, or vacation rentals in Kaanapali Hillside.
What are some of the best holiday rentals that Kaanapali Hillside has to offer?
Legendary Estate 50 Steps to Maui's Best Beach! New! 5 Bedroom, Pool With Slide!: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden. See all vacation rentals in Kaanapali Hillside.
If I need to cancel my hotel reservation in Kaanapali Hillside, will I receive a refund?
Yes, most hotel reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Kaanapali Hillside.
What are some accommodation options with pools in Kaanapali Hillside?
The Westin Maui Resort & Spa, Ka'anapali: Hotel steps from Whalers Village. Features 2 restaurants, 3 outdoor swimming pools and a full-service spa. Royal Lahaina Resort & Bungalows and OUTRIGGER Kaanapali Beach Resort are two additional hotels that offer an on-site pool. View all hotels with pools in Kaanapali Hillside.
How is it to stay in Kaanapali Hillside?
Those travelling to Kaanapali Hillside will definitely enjoy the sights to see and things to do. A top sight in the area is Kaanapali Beach. In Kaanapali Hillside, there are 5 hotels and other accommodation options to choose from. Find out more about Kaanapali Hillside.
What should I see while I'm in Kaanapali Hillside?
Kaanapali Beach is a notable place to visit in the area. You'll also find Kaanapali Kai Course at Kaanapali Golf Resort and Kaanapali Golf Courses in the area. Take a look at what more there is to see and do in Expedia's Kaanapali Hillside guide.
What's the seasonal weather in Kaanapali Hillside?
The hottest months are usually September and August, with an average temperature of 25°C, while the coldest months are February and March, with an average of 23°C. Average annual precipitation for Kaanapali Hillside is 224 mm.

Explore a world of travel with Expedia