Kaanapali Hillside Holiday Rentals, Hawaii: Private House Rentals

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Our top choices for Kaanapali Hillside hotels

A resort with a large pool, palm trees, and a view of the ocean.

A resort with multiple swimming pools, palm trees, and a beach view.

A gazebo with white columns and a metal roof, surrounded by lush tropical plants and a small water feature.

A woman in a swimsuit standing by a pool with a view of the ocean and palm trees.

1. The Westin Maui Resort & Spa, Ka'anapali

Kannapali Beach Area

Eugene

฿20,203

฿25,922 total

includes taxes & fees

30 Oct - 31 Oct

A resort with multiple swimming pools, a beach, and a mountain in the background.

A balcony with two rocking chairs and a small table, overlooking a pool and a beach with palm trees and a sunset view.

A resort with multiple buildings, a beach, and a pool area.

A resort with a swimming pool, palm trees, and a beach view.

2. Sheraton Maui Resort & Spa

Kannapali Beach Area

Eugene

฿11,041

฿15,298 total

includes taxes & fees

7 Oct - 8 Oct

A restaurant with outdoor seating overlooking a pond and waterfall, featuring wicker chairs and tables with green napkins.

An outdoor dining area with tables set for a meal, overlooking a body of water.

A beach view with palm trees, a clear sky, and a calm sea.

A pool area with a bridge, surrounded by lush greenery and a view of the sea.

3. Hyatt Regency Maui Resort & Spa

Kannapali Beach Area

Yoav

฿14,739

฿19,609 total

includes taxes & fees

30 Oct - 31 Oct

A hotel with a large building, a pond, and various tropical plants.

A spacious lobby with a central fountain, columns, and a thatched-roof structure.

A resort with a large pool, beachfront, and a mountain backdrop.

4. Hilton Vacation Club Ka'anapali Beach Maui

Kaanapali

Jordan

฿8,239

฿10,976 total

includes taxes & fees

23 Oct - 24 Oct

A resort with a swimming pool, palm trees, and a view of the ocean.

An aerial view of a resort with a beach, a swimming pool, and a large building with solar panels.

A resort with a pool, palm trees, and a view of the ocean.

A balcony with a view of a beach and palm trees.

5. OUTRIGGER Kaanapali Beach Resort

Kannapali Beach Area

Derick

฿9,027

฿12,509 total

includes taxes & fees

28 Oct - 29 Oct

A beach view with palm trees, a clear sky, and a distant mountain.

A room with a sofa, dining table, chairs, and large windows offering a view of the ocean.

A resort with a beach, pool, and ocean view.

A modern living room with a sectional sofa, a glass coffee table, and a view of the backyard.

6. Royal Lahaina Resort & Bungalows

Kannapali Beach Area

PHUONG

฿7,400

฿10,577 total

includes taxes & fees

3 Nov - 4 Nov

A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

A room with a view of the ocean, a ceiling fan, a large cabinet, and a red patterned rug.

A lobby with wicker furniture, a large mirror, and a view of the outdoors.

A beach with sun loungers, clear turquoise water, and a sailboat in the distance.

7. Aston Maui Kaanapali Villas

Kannapali Beach Area

Marie

฿7,400

฿11,772 total

includes taxes & fees

1 Nov - 2 Nov

A tropical garden with a waterfall, lush greenery, and a gazebo.

An aerial view of a resort with a central swimming pool surrounded by lounge chairs and palm trees.

8. Aston Kaanapali Shores

Lahaina

Roopa Rani

฿8,027

฿10,525 total

includes taxes & fees

10 Oct - 11 Oct

A view of a beach with palm trees and a sailboat on the water.

A landscaped garden with a pond, palm trees, and a view of the ocean.

A pool area with lounge chairs and umbrellas, a sign reading "The Whaler," and a view of the ocean and a mountain in the background.

A spacious living area with a large sliding glass door leading to a balcony, a sofa, a coffee table, and a dining area with chairs.

9. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

Alessio

฿8,235

฿22,038 total

includes taxes & fees

7 Oct - 8 Oct

A hotel with a stone facade, a pool with a waterfall, and lush greenery.

A modern outdoor lounge area with wicker furniture, a pool view, and a bar area.

A restaurant with outdoor seating overlooking a pool and palm trees, featuring wooden tables and chairs.

10. The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

Maria

฿18,766

฿22,278 total

includes taxes & fees

19 Oct - 20 Oct

A resort with a pool, palm trees, and a night scene with fire torches.

A modern office with a desk, computer, and chair, overlooking a pool and palm trees.

A beachfront hotel with multiple buildings, a pool area, and palm trees.

A pool with a waterfall, surrounded by rocks and palm trees, with a building in the background.

11. Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Kannapali Beach Area

Carroll M

฿17,149

฿20,358 total

includes taxes & fees

17 Oct - 18 Oct

A pool area with lounge chairs and palm trees, overlooking the ocean.

A golf course with a pool and resort buildings.

An outdoor dining area with tables and chairs, palm trees, and string lights against a backdrop of the ocean and sky.

An aerial view of a coastal area with a sandy beach, clear turquoise waters, and dense green forest.

12. The Ritz-Carlton Maui, Kapalua

Kapalua

TAMIKA

฿30,170

฿38,165 total

includes taxes & fees

4 Oct - 5 Oct

A spacious lobby with a stone-tiled floor, large wooden columns, and a reception desk.

A balcony with wicker furniture, a table, and chairs, overlooking a beach with palm trees and the ocean.

A beachside setting with wicker cabanas and palm trees.

An outdoor bar area with a thatched roof, wooden furniture, and a view of the ocean.

13. Hyatt Vacation Club at Ka'anapali Beach, Maui

Kannapali Beach Area

Javier

฿20,775

฿26,620 total

includes taxes & fees

19 Oct - 20 Oct

A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

A bedroom with a large bed, a ceiling fan, a painting, a balcony with a view of the ocean, and a seating area with a view.

A restaurant with a conical roof, surrounded by lush greenery and palm trees.

A tropical garden with a small water feature, palm trees, and lush greenery.

14. Napili Shores Maui by OUTRIGGER

Lahaina

Diana

฿7,259

฿8,617 total

includes taxes & fees

29 Oct - 30 Oct

A resort pool with red umbrellas, palm trees, and a view of the ocean.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

A dining area with a view of the ocean and a mountain in the distance.

A tropical resort with thatched-roof structures, palm trees, and a sign indicating breakfast, lunch, dinner, and cocktails.

15. OUTRIGGER Honua Kai Resort & Spa

Lahaina

Aprille A

฿12,655

฿32,900 total

includes taxes & fees

26 Oct - 27 Oct

A balcony with a glass table, two wicker chairs, and a potted plant with yellow flowers.

A beach with palm trees, a clear blue sky, and a calm sea.

A pathway lined with tropical plants and palm trees, leading to a building with a balcony.

A wooden entrance with a sign reading "The Mauian" and two benches in front.

16. The Mauian - Boutique Beach Studios on Napili Bay

Lahaina

Iolani

฿7,323

฿8,693 total

includes taxes & fees

14 Oct - 15 Oct

A spacious living room with a large window overlooking the ocean, furnished with wicker chairs, a sofa, and a glass coffee table.

A hotel room with a bed, a desk, a chair, a small table, and a view of the ocean.

A spacious lobby with a large bench, potted plants, and a view of the beach through large windows.

A modern hotel room with a large balcony, a kitchen area, and a bed with a view of the ocean.

17. Aston Mahana at Kaanapali

Kaanapali

Amit

฿8,296

฿10,844 total

includes taxes & fees

7 Oct - 8 Oct

A multi-story hotel with a pool, garden, and ocean view.

A beach with clear turquoise water, a sandy shore, and several boats. There are palm trees and a building in the background.

A modern outdoor seating area with a view of a bridge and a landscaped garden.

18. Aston at The Whaler on Kaanapali Beach

Kannapali Beach Area

Stewart

฿11,786

฿20,923 total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a table set for dining, overlooking a pool and palm trees, with a view of the ocean and mountains in the distance.

A balcony with a view of the ocean and palm trees.

A high-rise hotel with a green roof, located near a beach with a view of the ocean and a sunset.

A resort with multiple swimming pools, palm trees, and a view of the ocean at sunset.

19. Honua Kai Konea Resort by KBM

Kaanapali

Jane

฿15,936

฿35,372 total

includes taxes & fees

10 Oct - 11 Oct

A resort with a pool, palm trees, a waterfall, and a view of the ocean.

A balcony with a view of the ocean and palm trees, a dining area with chairs, and a small table with a vase of flowers.

A hotel lobby with a central seating area, a large chandelier, and a view of the pool and palm trees.

A resort with a large pool, palm trees, and a view of the ocean at sunset.

20. The Westin Ka'anapali Ocean Resort Villas

Kannapali Beach Area

James

฿16,612

฿19,720 total

includes taxes & fees

13 Oct - 14 Oct

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Top Kaanapali Hillside Hotel Reviews

Aston Kaanapali Shores

10/10 Excellent

"Very beautiful property, friendly staff. We had a wonderful experience and we will return to the property on our next Maui visit"

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"My FIRST time ever to Hawaii! I had to see this place not just for its location on Kaanapali Beach, but that it was recommended by Great Value Vacations. Quite the drive from the airport, and it was tricky to park as the garage has narrow spaces, but I loved my first hotel in the Aloha State! The food, the beach, the staff, the sunsets, and the rooms lived up to all my expectations."

Napili Shores Maui by OUTRIGGER

10/10 Excellent

"Clean room"

Royal Lahaina Resort & Bungalows

10/10 Excellent

"The room was clean, and I loved the mature, relaxing atmosphere of the property. The bell desk and restaurant staff were excellent. They were all friendly, attentive, and welcoming. The morning yoga class was amazing, with a wonderful instructor who made the experience really enjoyable. I also loved the live music every evening. It added such a nice touch to the atmosphere. The only small negative was the check in and check out experience at the front desk. One of the staff members didn’t seem particularly enthusiastic about her job, which felt a little different from the otherwise warm and welcoming service throughout the hotel. Overall, we really enjoyed our stay and especially appreciated the beautiful atmosphere, yoga, live music, and excellent service from most of the staff."

Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent

"We loved our 10 day stay at the Hilton Vacation Club. Would highly recommend! We especially enjoyed the location and the excellent nearby beaches for snorkeling, the pool area, the room with a lovely bathroom, comfy bed, kitchen supplies, the friendly, helpful staff, mini golf course on site, supermarket across the road, and a nice church and restaurants within walking distance. Just a great spot!"

AEI at Maui Kaanapali Villas Resort

10/10 Excellent

"Room was clean and spacious. Staff was very helpful. Rain at the front desk is amazing!"

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent

"Our week here was top tier! Staff were friendly and helpful, our room was stunning, and the property was in the perfect location. Will definitely stay here again in the future."

Sheraton Maui Resort & Spa

10/10 Excellent

"Clean"

Aston at Papakea Resort

10/10 Excellent

"Great resort and we'd definitely stay again!"

More cheap stays in Kaanapali Hillside

Hotel Lanai

828 Lanai Ave Lanai City HI

฿12,987

฿15,418 total

4 Oct - 5 Oct

includes taxes & fees

The Historic Wailuku Inn

2199 Kahookele St Wailuku HI

฿6,416

฿15,533 total

4 Oct - 5 Oct

includes taxes & fees

8.6/10 Excellent! (42 reviews)

Maui Beach Vacation Club

515 S. Kihei Road Kihei HI

Get rates

8.4/10 Very good! (962 reviews)

Kaanapali Ocean Inn

2780-A Kekaa Dr Lahaina HI

Get rates

Petite Retreat at Kahana Falls

4260 Lower Honoapiilani Rd Lahaina HI

Get rates

7.8/10 Good! (17 reviews)

The Plantation Inn

174 Lahainaluna Road Lahaina HI

Get rates

9.6/10 Exceptional! (61 reviews)

Frequently asked questions

What's the best place for a stay in Kaanapali Hillside?

Royal Lahaina Resort & Bungalows, located 0.8 mi (1.3 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 The Westin Maui Resort & Spa, Ka'anapali and Aston Kaanapali Shores. See all available top hotels, or 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?

Royal Lahaina Resort & Bungalows: Hotel, 8-minute walk from Kaanapali Beach. Features a full-service spa, 2 outdoor swimming pools and 2 bars. The Westin Maui Resort & Spa, Ka'anapali and Aston Kaanapali Shores 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. Top sights around the area include Kaanapali Beach and Whalers Village. 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?

Notable places to visit in the surrounding area include Kaanapali Beach and Whalers Village. You'll also find Kahekili Beach and Kaanapali Kai Course at Kaanapali Golf Resort 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.

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Find hotels in Kaanapali Hillside, HI from ฿8,617

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Kaanapali Hillside

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Kaanapali Hillside hotels

1. The Westin Maui Resort & Spa, Ka'anapali

2. Sheraton Maui Resort & Spa

3. Hyatt Regency Maui Resort & Spa

4. Hilton Vacation Club Ka'anapali Beach Maui

5. OUTRIGGER Kaanapali Beach Resort

6. Royal Lahaina Resort & Bungalows

7. Aston Maui Kaanapali Villas

8. Aston Kaanapali Shores

9. The Whaler Resort Kaanapali Beach

10. The Westin Nanea Ocean Villas, Ka'anapali

11. Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

12. The Ritz-Carlton Maui, Kapalua

13. Hyatt Vacation Club at Ka'anapali Beach, Maui

14. Napili Shores Maui by OUTRIGGER

15. OUTRIGGER Honua Kai Resort & Spa

16. The Mauian - Boutique Beach Studios on Napili Bay

17. Aston Mahana at Kaanapali

18. Aston at The Whaler on Kaanapali Beach

19. Honua Kai Konea Resort by KBM

20. The Westin Ka'anapali Ocean Resort Villas

Top Kaanapali Hillside Hotel Reviews

Aston Kaanapali Shores

OUTRIGGER Kaanapali Beach Resort

Napili Shores Maui by OUTRIGGER

Royal Lahaina Resort & Bungalows

Hilton Vacation Club Ka'anapali Beach Maui

AEI at Maui Kaanapali Villas Resort

Hilton Grand Vacations Club Maui Bay Villas

Sheraton Maui Resort & Spa

Aston at Papakea Resort

More cheap stays in Kaanapali Hillside

Hotel Lanai

The Historic Wailuku Inn

Maui Beach Vacation Club

Kaanapali Ocean Inn

Petite Retreat at Kahana Falls

The Plantation Inn

Frequently asked questions

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