Kaanapali Hillside Vacation Rentals from AED 781: Search Short-Term Rentals

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Our top choices for Kaanapali Hillside vacation rentals

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

1. Aston Kaanapali Shores

Lahaina

Roopa Rani

AED 1,152 total

includes taxes & fees

10 Oct - 11 Oct

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

2. Aston Maui Kaanapali Villas

Kannapali Beach Area

Marie

AED 1,288 total

includes taxes & fees

1 Nov - 2 Nov

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

3. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

Alessio

AED 2,412 total

includes taxes & fees

7 Oct - 8 Oct

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

4. Napili Village Hotel

Lahaina

ASHLEY

AED 781 total

includes taxes & fees

1 Nov - 2 Nov

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

5. Napili Shores Maui by OUTRIGGER

Lahaina

Diana

AED 1,065 total

includes taxes & fees

17 Oct - 18 Oct

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

6. OUTRIGGER Honua Kai Resort & Spa

Lahaina

Aprille A

AED 3,601 total

includes taxes & fees

26 Oct - 27 Oct

A beach view with lounge chairs and a clear sky.

7. Napili Sunset on the Beach

Lahaina

Beverly

AED 1,226 total

includes taxes & fees

4 Oct - 5 Oct

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

8. The Westin Ka'anapali Ocean Resort Villas

Kannapali Beach Area

James

AED 2,158 total

includes taxes & fees

11 Oct - 12 Oct

A swimming pool with lounge chairs and palm trees in the background.

9. Summertime Special Prices!! Book Now!

Kannapali Beach Area

Karen K.

AED 2,216 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a central island, stainless steel appliances, and a view to a patio area.

10. Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

Kannapali Beach Area

Emily A.

AED 2,150 total

includes taxes & fees

4 Oct - 5 Oct

11. Aston at The Whaler on Kaanapali Beach

Kannapali Beach Area

Stewart

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

12. Aston Mahana at Kaanapali

Kaanapali

Amit

AED 1,187 total

includes taxes & fees

7 Oct - 8 Oct

A round table with a bottle, a glass, a loaf of bread, grapes, and a vase with flowers.

13. Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym

Kannapali Beach Area

Stephanie S.

AED 1,785 total

includes taxes & fees

28 Oct - 29 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.

14. Honua Kai Konea Resort by KBM

Kaanapali

Jane

AED 3,871 total

includes taxes & fees

10 Oct - 11 Oct

A round table with two chairs on a balcony overlooking a clear blue sea and a distant mountain.

15. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

Lahaina

Anthony P.

AED 1,790 total

includes taxes & fees

10 Oct - 11 Oct

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

16. Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

Kannapali Beach Area

Alaba G.

AED 3,309 total

includes taxes & fees

10 Oct - 11 Oct

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

17. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Lahaina

Michael

AED 2,772 total

includes taxes & fees

5 Oct - 6 Oct

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

18. The Westin Nanea Ocean Villas, Ka'anapali

Lahaina

Maria

AED 2,438 total

includes taxes & fees

19 Oct - 20 Oct

A beachfront hotel with clear turquoise waters, lush greenery, and palm trees.

19. Direct Oceanfront ground floor - Kuleana 706

Lahaina

Margarita R.

AED 3,124 total

includes taxes & fees

4 Oct - 5 Oct

A beach with clear blue water and a sandy shore.

20. Top Floor, Corner Unit, Pool View, Kaanapali Beach

Kannapali Beach Area

Terri B.

AED 1,785 total

includes taxes & fees

5 Oct - 6 Oct

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Top Kaanapali Hillside Hotel Reviews

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."

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!"

Frequently asked questions

Can I find a vacation rental in Kaanapali Hillside?

Yes, we have vacation rentals near well known sights in Kaanapali Hillside, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Kaanapali Hillside?

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!: Visitors like this Kaanapali Hillside vacation home rental. It is located on the beach and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

What’s there to see and do in Kaanapali Hillside?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kaanapali Beach. Whalers Village and Kahekili Beach are a couple of places you'll find in the larger area.

What’s a vacation rental in Kaanapali Hillside like?

A vacation rental is a private property you can book for a long or short time in Kaanapali Hillside. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.

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Check prices for these dates

Our top choices for Kaanapali Hillside vacation rentals

1. Aston Kaanapali Shores

2. Aston Maui Kaanapali Villas

3. The Whaler Resort Kaanapali Beach

4. Napili Village Hotel

5. Napili Shores Maui by OUTRIGGER

6. OUTRIGGER Honua Kai Resort & Spa

7. Napili Sunset on the Beach

8. The Westin Ka'anapali Ocean Resort Villas

9. Summertime Special Prices!! Book Now!

10. Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

11. Aston at The Whaler on Kaanapali Beach

12. Aston Mahana at Kaanapali

13. Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym

14. Honua Kai Konea Resort by KBM

15. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

16. Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

17. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

18. The Westin Nanea Ocean Villas, Ka'anapali

19. Direct Oceanfront ground floor - Kuleana 706

20. Top Floor, Corner Unit, Pool View, Kaanapali Beach

Find vacation rentals that suit your style

Top Kaanapali Hillside Hotel Reviews

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

The Whaler Resort Kaanapali Beach

Aston at Papakea Resort

Frequently asked questions

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