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Kaanapali Hillside Vacation Rentals

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Our top choices for Kaanapali Hillside vacation rentals

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,658 reviews)
"Amazing and relaxing resort"
United States
Mariano
The price is CA $257
CA $430 total
includes taxes & fees
Nov 21 - Nov 22
Aston Maui Kaanapali Villas

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,432 reviews)
"Great stay at a great price"
United States
Dina
The price is CA $238
CA $324 total
includes taxes & fees
Nov 11 - Nov 12
Aston Kaanapali Shores

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (518 reviews)
"Amazing stay!"
United States
zachary
The price is CA $296
CA $867 total
includes taxes & fees
Dec 1 - Dec 2
The Whaler Resort Kaanapali Beach

4. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (259 reviews)
"amazing location"
United States
Adrian
The price is CA $265
CA $314 total
includes taxes & fees
Nov 9 - Nov 10
Napili Village Hotel

5. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,093 reviews)
"Nice and clean resort, staff was very friendly and accommodating"
United States
Trung
The price is CA $480
CA $1,222 total
includes taxes & fees
Dec 9 - Dec 10
OUTRIGGER Honua Kai Resort & Spa

6. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (1,170 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is CA $485
CA $575 total
includes taxes & fees
Nov 20 - Nov 21
The Westin Ka'anapali Ocean Resort Villas

7. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,913 reviews)
"Very nice location and grounds. Throughly enjoyed our stay!"
United States
Steve
The price is CA $348
CA $411 total
includes taxes & fees
Nov 11 - Nov 12
Napili Shores Maui by OUTRIGGER

8. Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (234 reviews)
"Best resort for kids"
United States
Mai Ka
The price is CA $506
CA $600 total
includes taxes & fees
Dec 7 - Dec 8
Marriott's Maui Ocean Club - Lahaina & Napili Towers

9. The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach
Kannapali Beach Area
9.6 out of 10, Exceptional, (82 reviews)
"Good view, good location!"
United States
Nate M.
The price is CA $325
CA $1,376 total
includes taxes & fees
Nov 21 - Nov 22
The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

10. Kuleana Club - 316

Kuleana Club - 316
3.5 star property
Lahaina
10.0 out of 10, Exceptional, (3 reviews)
"Excellent place! Great views of the beach and the sunset."
United States
Howie
The price is CA $220
CA $555 total
includes taxes & fees
Nov 12 - Nov 13
Kuleana Club - 316

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

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (111 reviews)
"Everything was great !"
United States
Michael
The price is CA $151
CA $1,131 total
includes taxes & fees
Nov 9 - Nov 10
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

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

Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Kannapali Beach Area
10.0 out of 10, Exceptional, (206 reviews)
"Loved this place. Perfect! Grounds and room very clean and well equipped kitchen with even Tupperware. Great lay out with plenty of space. Lovely lanai and walking distance to the beach or golf cart ride. Covered building cabana with outdoor shower and bathrooms with use of beach chairs. Close to shops and pickleball."
United States
Robert C.
The price is CA $286
CA $911 total
includes taxes & fees
Nov 14 - Nov 15
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

13. Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views

Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views
Lahaina
10.0 out of 10, Exceptional, (325 reviews)
"We loved our stay. Beautiful patio view & very walkable to many restaurants, bakeries & coffee spots. "
United States
Richard H.
The price is CA $326
CA $767 total
includes taxes & fees
Dec 3 - Dec 4
Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views

14. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Kannapali Beach Area
10.0 out of 10, Exceptional, (177 reviews)
"Great location. Place had all the facilities for a wonderful stay and close to the golf courses."
United States
Brent T.
The price is CA $242
CA $811 total
includes taxes & fees
Nov 12 - Nov 13
Summertime Special Prices!! Book Now!

15. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
The price is CA $344
CA $409 total
includes taxes & fees
Dec 9 - Dec 10
Napili Sunset on the Beach

16. The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (546 reviews)
"great family stay"
United States
Justin
The price is CA $565
CA $671 total
includes taxes & fees
Dec 2 - Dec 3
The Westin Nanea Ocean Villas, Ka'anapali

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

Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!
Lahaina
9.8 out of 10, Exceptional, (179 reviews)
"Condo had a great view of turtles playing in the water right off the beach. Snorkeling in front of the condo was pretty good but better just north of the property."
United States
joseph s.
The price is CA $233
CA $639 total
includes taxes & fees
Nov 12 - Nov 13
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

18. Spacious Studio Close to Ocean Heated Pool - Kaleialoha 402

Spacious Studio Close to Ocean Heated Pool - Kaleialoha 402
Lahaina
9.6 out of 10, Exceptional, (47 reviews)
"We loved this property and would stay here again."
United States
Barry K.
The price is CA $126
CA $1,003 total
includes taxes & fees
Nov 11 - Nov 12
Spacious Studio Close to Ocean Heated Pool - Kaleialoha 402

19. Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
Lahaina
8.8 out of 10, Excellent, (114 reviews)
"Great location and wonderful resort to stay at."
United States
Daniel S.
The price is CA $150
CA $1,130 total
includes taxes & fees
Nov 9 - Nov 10
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

20. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
Lahaina
9.8 out of 10, Exceptional, (280 reviews)
"We had a great time in Maui! We were there to rest and relax and celebrate our anniversary."
United States
Traci B.
The price is CA $235
CA $705 total
includes taxes & fees
Nov 15 - Nov 16
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
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.
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Top Kaanapali Hillside Hotel Reviews

Find out more about Kaanapali Hillside

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kaanapali Hillside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.