Kaanapali Hillside Holiday Rentals, Hawaii: Private House Rentals

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Our top choices for Kaanapali Hillside hotels

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

A covered outdoor area with a table and chairs, overlooking a lush garden and a view of the ocean.

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.

1. Aston Maui Kaanapali Villas

Kannapali Beach Area

Sabrina

5.697.666 ₫

9.077.711 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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.

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

2. OUTRIGGER Kaanapali Beach Resort

Kannapali Beach Area

Derick

6.992.117 ₫

9.689.029 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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

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

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

3. Royal Lahaina Resort & Bungalows

Kannapali Beach Area

Anthony

5.731.456 ₫

8.192.472 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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.

4. Aston Kaanapali Shores

Lahaina

Shad

4.653.820 ₫

6.296.116 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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

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 a swimming pool, palm trees, and a beach view.

5. Sheraton Maui Resort & Spa

Kannapali Beach Area

Eugene

10.787.095 ₫

14.307.971 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

6. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

Luis A

6.066.766 ₫

16.699.140 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

A beach with palm trees and a rainbow over the ocean.

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

Kannapali Beach Area

Matthew

15.647.786 ₫

20.078.196 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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

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

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

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

8. Hyatt Regency Maui Resort & Spa

Kannapali Beach Area

SHOHAG

11.832.014 ₫

15.558.033 ₫ total

includes taxes & fees

12 Sept - 13 Sept

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

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.

9. The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

Hassenat

14.535.286 ₫

17.255.130 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

10. Hilton Vacation Club Ka'anapali Beach Maui

Kaanapali

Lenie

5.942.000 ₫

7.979.478 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

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.

11. The Mauian - Boutique Beach Studios on Napili Bay

Lahaina

Daniel

5.671.654 ₫

6.732.934 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

A tropical resort with palm trees, thatched-roof structures, 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.

12. OUTRIGGER Honua Kai Resort & Spa

Lahaina

Diana

9.128.846 ₫

24.683.766 ₫ total

includes taxes & fees

10 Oct - 11 Oct

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

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

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

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

13. Napili Shores Maui by OUTRIGGER

Lahaina

Diana

6.413.773 ₫

7.613.918 ₫ total

includes taxes & fees

12 Sept - 13 Sept

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

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

An outdoor dining area with a stone table and benches, overlooking a body of water and a sailboat.

14. Aston at The Whaler on Kaanapali Beach

Kannapali Beach Area

Heidi

5.468.927 ₫

11.861.378 ₫ total

includes taxes & fees

30 Sept - 1 Oct

A beach with clear blue water, palm trees, and a resort in the background.

A building with a pool, surrounded by tropical vegetation and palm trees, overlooking a clear blue ocean.

A pool area with lounge chairs, a building with a balcony, and palm trees.

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

15. Napili Village Hotel

Lahaina

Alysson E

4.906.438 ₫

5.824.531 ₫ total

includes taxes & fees

15 Sept - 16 Sept

A beach view with lounge chairs and a clear sky.

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

A spacious living area with a dining table, chairs, a red sofa, a staircase, and a kitchen in the background.

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

16. Napili Sunset on the Beach

Lahaina

Chris

7.308.452 ₫

8.676.204 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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.

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

Kannapali Beach Area

Carroll M

13.282.423 ₫

15.767.830 ₫ total

includes taxes & fees

23 Sept - 24 Sept

A pool area with lounge chairs and a view of the ocean.

A hotel room with two beds, a small desk, and a large wall mural.

A modern living room with a grey sofa, a coffee table, and a dining table with chairs. There is a ceiling fan, a balcony with a view of palm trees, and a large window.

18. Maui Seaside Hotel

Kahului

Anthony

4.676.205 ₫

6.322.689 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

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

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.

19. The Westin Ka'anapali Ocean Resort Villas

Kannapali Beach Area

Brenda

12.866.535 ₫

15.274.123 ₫ total

includes taxes & fees

15 Sept - 16 Sept

A grassy area with white lounge chairs, palm trees, and a view of the ocean.

A kitchen with a view of the ocean, a ceiling fan, and a coffee maker.

A hotel room with two beds, a sofa, and a large window offering a view of the sea.

An aerial view of a beach with clear turquoise water, a sandy shore, and patches of green vegetation.

20. Maui Beach Hotel

Kahului

Wilfredo

4.112.807 ₫

5.499.470 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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Top Kaanapali Hillside Hotel Reviews

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 👍🙏🙏🙏🌺🌺"

The Whaler Resort Kaanapali Beach

10/10 Excellent

"Great location. Loved hearing the waves crashing and watching the sunset from our balcony. Lots of shops and restaurants in walking distance. We will stay again."

Napili Shores Maui by OUTRIGGER

8/10 Good

"A no frills stay but excellent location. Grounds are pretty, rooms and buildings don’t do much for aesthetics but they’re clean (when you arrive...) I really hated that they only clean rooms in between guests. We needed to go to the front desk for towels regularly, and wished our sheets were changed within our 5 day stay. The staff on deck for activities was friendly and knowledgeable, which was super convenient. The location is FANTASTIC. The beach is calm, very relaxing. Great for snorkeling, easy to walk to a nicer resort for dinner. We visited lots of different beaches but nothing beat our little walk from the hotel at sunset."

Sheraton Maui Resort & Spa

10/10 Excellent

"Muy buen hotel"

Royal Lahaina Resort & Bungalows

10/10 Excellent

"I loved this stay"

Napili Kai Beach Resort

8/10 Good

"We stayed in Unit 202 from August 29 through September 5. While the property is approximately 65 years old, the furniture in the unit appeared just as dated. I understand that this is a timeshare, but at nearly $1,000 per night, the owner should seriously consider updating the furnishings. At that price, guests should expect a more modern and comfortable interior. On a positive note, the bed was very comfortable, the property’s location was excellent, and the staff was wonderful. A special thank-you to Kim, the concierge, who was absolutely incredible and made our experience much better. Would I stay here again? Probably not, mainly because the price does not reflect the condition and age of the furnishings."

The Ritz-Carlton Maui, Kapalua

10/10 Excellent

"Stay was comfortable staff very attentive & accomodating, We stayed in the fire lanai deluxe room (ocen-view) it was amazing. Be prepared to get your steps in going from your room to the main lobby if you’re staying over there, but you will have easy access to the pool and the exclusion will be very much appreciated. Def worth it!!"

More cheap stays in Kaanapali Hillside

The Historic Wailuku Inn

2199 Kahookele St Wailuku HI

3.465.487 ₫

10.073.664 ₫ total

23 Sept - 24 Sept

includes taxes & fees

8.6/10 Excellent! (41 reviews)

Hotel Lanai

828 Lanai Ave Lanai City HI

10.059.291 ₫

11.941.586 ₫ total

12 Sept - 13 Sept

includes taxes & fees

9.4/10 Exceptional! (19 reviews)

Maui Beach Vacation Club

515 S. Kihei Road Kihei HI

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Kaanapali Ocean Inn

2780-A Kekaa Dr Lahaina HI

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The Plantation Inn

174 Lahainaluna Road Lahaina HI

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9.6/10 Exceptional! (61 reviews)

Suite Maui Paradise Condo

Wailuku HI

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Frequently asked questions

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 5.824.531 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Kaanapali Hillside

Check prices for these dates

Filter by

Star rating

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Our top choices for Kaanapali Hillside hotels

1. Aston Maui Kaanapali Villas

2. OUTRIGGER Kaanapali Beach Resort

3. Royal Lahaina Resort & Bungalows

4. Aston Kaanapali Shores

5. Sheraton Maui Resort & Spa

6. The Whaler Resort Kaanapali Beach

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

8. Hyatt Regency Maui Resort & Spa

9. The Westin Nanea Ocean Villas, Ka'anapali

10. Hilton Vacation Club Ka'anapali Beach Maui

11. The Mauian - Boutique Beach Studios on Napili Bay

12. OUTRIGGER Honua Kai Resort & Spa

13. Napili Shores Maui by OUTRIGGER

14. Aston at The Whaler on Kaanapali Beach

15. Napili Village Hotel

16. Napili Sunset on the Beach

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

18. Maui Seaside Hotel

19. The Westin Ka'anapali Ocean Resort Villas

20. Maui Beach Hotel

Top Kaanapali Hillside Hotel Reviews

Maui Beach Hotel

Aston Maui Kaanapali Villas

Courtyard Maui Kahului Airport

The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

Sheraton Maui Resort & Spa

Royal Lahaina Resort & Bungalows

Napili Kai Beach Resort

The Ritz-Carlton Maui, Kapalua

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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