Kaanapali Hillside Holiday Rentals, Hawaii: Private House Rentals

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Our top choices for Kaanapali Hillside hotels

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

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

An aerial view of a resort with a swimming pool, palm trees, and a beach.

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

1. OUTRIGGER Kaanapali Beach Resort

Kannapali Beach Area

Derick

฿9,180

฿12,656 total

includes taxes & fees

16 Sept - 17 Sept

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

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

A spacious indoor area with a large wooden table, comfortable seating, and large windows offering a view of the ocean.

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

2. Sheraton Maui Resort & Spa

Kannapali Beach Area

Eugene

฿13,655

฿18,112 total

includes taxes & fees

13 Sept - 14 Sept

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

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

A dining area with a wooden table set for four, two chairs, and a view of the ocean.

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

3. Royal Lahaina Resort & Bungalows

Kannapali Beach Area

Anthony

฿7,255

฿10,371 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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.

4. Aston Maui Kaanapali Villas

Kannapali Beach Area

Sabrina

฿7,213

฿11,491 total

includes taxes & fees

11 Sept - 12 Sept

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

A beach with palm trees and a rainbow over 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.

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

Kannapali Beach Area

Matthew

฿19,808

฿25,417 total

includes taxes & fees

11 Sept - 12 Sept

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

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.

A room with two beds, a bathtub, and a large window with a view of the sea.

6. Hyatt Regency Maui Resort & Spa

Kannapali Beach Area

SHOHAG

฿14,978

฿19,695 total

includes taxes & fees

12 Sept - 13 Sept

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

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

7. Hilton Vacation Club Ka'anapali Beach Maui

Kaanapali

Lenie

฿7,522

฿10,101 total

includes taxes & fees

25 Sept - 26 Sept

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.

8. The Westin Ka'anapali Ocean Resort Villas

Kannapali Beach Area

Brenda

฿16,287

฿19,335 total

includes taxes & fees

17 Sept - 18 Sept

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

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

9. Aston Kaanapali Shores

Lahaina

Shad

฿5,891

฿7,970 total

includes taxes & fees

19 Sept - 20 Sept

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

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

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.

10. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

Luis A

฿7,680

฿21,139 total

includes taxes & fees

5 Oct - 6 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 tropical resort with thatched-roof structures, palm trees, and a sign indicating breakfast, lunch, dinner, and cocktails.

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

11. OUTRIGGER Honua Kai Resort & Spa

Lahaina

Diana

฿11,719

฿31,440 total

includes taxes & fees

12 Sept - 13 Sept

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

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.

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

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

Kannapali Beach Area

Russell John Kilkenny

฿18,882

฿24,328 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

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

Kannapali Beach Area

Carroll M

฿16,814

฿19,960 total

includes taxes & fees

23 Sept - 24 Sept

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

A grassy area with palm trees and a building with a thatched roof.

14. Napili Shores Maui by OUTRIGGER

Lahaina

Diana

฿9,106

฿10,810 total

includes taxes & fees

19 Sept - 20 Sept

A tropical resort with a view of the ocean, palm trees, and a pathway leading to a beach.

A dining table set with wicker chairs, a floral centerpiece, and drinks on a balcony overlooking a beach with palm trees and a mountain in the background.

A spacious kitchen with a central island, a dining area with a view of the ocean, and a living room with a large window overlooking the sea.

15. Honua Kai Hokulani Resort by KBM

Kaanapali

Lance

฿17,531

฿42,412 total

includes taxes & fees

19 Sept - 20 Sept

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

A courtyard with a long reflective pool, surrounded by lush greenery and palm trees.

16. The Mauian - Boutique Beach Studios on Napili Bay

Lahaina

Daniel

฿7,180

฿8,523 total

includes taxes & fees

21 Sept - 22 Sept

A beach view with lounge chairs and a clear sky.

A glass table with chairs in a tropical setting, overlooking a swimming pool and surrounded by lush greenery.

A beachside resort with palm trees, lounge chairs, and a view of the ocean.

A modern kitchen with white appliances, wooden cabinets, and a central island.

17. Napili Sunset on the Beach

Lahaina

Chris

฿9,252

฿10,983 total

includes taxes & fees

11 Sept - 12 Sept

An aerial view of a resort with a beach, a swimming pool, and palm trees.

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

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

18. The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

Hassenat

฿18,400

฿21,843 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

19. Aston at The Whaler on Kaanapali Beach

Kannapali Beach Area

Heidi

฿6,923

฿15,015 total

includes taxes & fees

30 Sept - 1 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.

A covered outdoor seating area with a fire pit, overlooking a pool and lush greenery.

20. The Ritz-Carlton Maui, Kapalua

Kapalua

TAMIKA

฿26,290

฿33,514 total

includes taxes & fees

11 Sept - 12 Sept

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Top Kaanapali Hillside Hotel Reviews

Aston Kaanapali Shores

10/10 Excellent

"Clean room, fully equipped, laundry set with complimentary laundry detergent, ice maker, and spacious. Only thing is the salon restroom could be more equipped for those with late flights, such as lotion, toiletries to use, hair dryers, and a sturdy shower curtain. Mine fell on me a few times while soaking wet."

Maui Beach Hotel

8/10 Good

"Great staff"

Aston Maui Kaanapali Villas

10/10 Excellent

"Beautiful beachfront property with lush gardens!"

Courtyard Maui Kahului Airport

10/10 Excellent

"Todo estuvo perfecto gracias voy a regresar 👍🙏🙏🙏🌺🌺"

Maui Seaside Hotel

10/10 Excellent

"Very friendly staff"

Napili Shores Maui by OUTRIGGER

8/10 Good

"Not a bad view, but no direct access to ocean. Has a cliff with rocks. Beach access is further away to the right. Room had ants coming in n out of back sliding door and also small tiny bugs/lice. Which are probably harmless but kinda gross cuz they were even inside the microwave and were resistant to the microwave when on. Overall a good place to stay with two pools and not a bad view, even though we were here during three hurricanes being around, but we were not affected other than big waves and wind/clouds."

OUTRIGGER Honua Kai Resort & Spa

10/10 Excellent

"Loved the oceanview from our room! Room was spacious and clean. Full kitchen was a plus and stores were close by. Even had a general store on site. Loved this place!"

Sheraton Maui Resort & Spa

10/10 Excellent

"Muy buen hotel"

Royal Lahaina Resort & Bungalows

10/10 Excellent

"I loved this stay"

More cheap stays in Kaanapali Hillside

The Historic Wailuku Inn

2199 Kahookele St Wailuku HI

฿5,472

฿14,145 total

14 Sept - 15 Sept

includes taxes & fees

8.6/10 Excellent! (41 reviews)

Hotel Lanai

828 Lanai Ave Lanai City HI

฿12,734

฿15,117 total

12 Sept - 13 Sept

includes taxes & fees

9.4/10 Exceptional! (19 reviews)

Maui Beach Vacation Club

515 S. Kihei Road Kihei HI

Get rates

8.4/10 Very good! (945 reviews)

Kaanapali Ocean Inn

2780-A Kekaa Dr Lahaina HI

Get rates

The Plantation Inn

174 Lahainaluna Road Lahaina HI

Get rates

9.6/10 Exceptional! (61 reviews)

Suite Maui Paradise Condo

Wailuku HI

Get rates

Frequently asked questions

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

Hyatt Regency Maui Resort & Spa, located 1.2 mi (1.9 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 Ritz-Carlton Maui, Kapalua and Aston Kaanapali Shores. 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?

Kapalua Golf Villas Resort by KBM: 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. Kitchen amenities include a fridge, an oven and a microwave. Kick off your shoes and enjoy yourself with a terrace and 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?

Hyatt Regency Maui Resort & Spa: Resort, 4-minute walk from Kaanapali Beach. Features 6 outdoor swimming pools, a children's pool and 4 restaurants. The Ritz-Carlton Maui, Kapalua 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 ฿7,373

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Kaanapali Hillside

Check prices for these dates

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Our top choices for Kaanapali Hillside hotels

1. OUTRIGGER Kaanapali Beach Resort

2. Sheraton Maui Resort & Spa

3. Royal Lahaina Resort & Bungalows

4. Aston Maui Kaanapali Villas

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

6. Hyatt Regency Maui Resort & Spa

7. Hilton Vacation Club Ka'anapali Beach Maui

8. The Westin Ka'anapali Ocean Resort Villas

9. Aston Kaanapali Shores

10. The Whaler Resort Kaanapali Beach

11. OUTRIGGER Honua Kai Resort & Spa

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

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

14. Napili Shores Maui by OUTRIGGER

15. Honua Kai Hokulani Resort by KBM

16. The Mauian - Boutique Beach Studios on Napili Bay

17. Napili Sunset on the Beach

18. The Westin Nanea Ocean Villas, Ka'anapali

19. Aston at The Whaler on Kaanapali Beach

20. The Ritz-Carlton Maui, Kapalua

Top Kaanapali Hillside Hotel Reviews

Aston Kaanapali Shores

Maui Beach Hotel

Aston Maui Kaanapali Villas

Courtyard Maui Kahului Airport

Maui Seaside Hotel

Napili Shores Maui by OUTRIGGER

OUTRIGGER Honua Kai Resort & Spa

Sheraton Maui Resort & Spa

Royal Lahaina Resort & Bungalows

More cheap stays in Kaanapali Hillside

The Historic Wailuku Inn

Hotel Lanai

Maui Beach Vacation Club

Kaanapali Ocean Inn

The Plantation Inn

Suite Maui Paradise Condo

Frequently asked questions

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