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Kaanapali Hillside Vacation Rentals

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Our top choices for Kaanapali Hillside vacation rentals

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,143 reviews)
"Great Stay!!"
United States
Christopher
The price is CA $423
CA $544 total
includes taxes & fees
Jun 24 - Jun 25
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,582 reviews)
"The villa we stayed was new, beautiful and quiet. Perfect for a serene and private get away. Felt non touristy and accessible."
United States
Aylin
The price is CA $367
CA $561 total
includes taxes & fees
Jun 23 - Jun 24
Aston Maui Kaanapali Villas

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (192 reviews)
"Amazing location, great garden/ pool view. Comfortable and clean room, close to beach and snorkeling. Would definitely stay there again."
United States
Patrick James
The price is CA $280
CA $332 total
includes taxes & fees
Jul 5 - Jul 6
Napili Village Hotel

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (422 reviews)
"The location is simply outstanding with easy access to public transit, shopping food, and it’s literally on the beach. The views from our balcony were fabulous."
United States
Mackenzie
The price is CA $432
CA $1,030 total
includes taxes & fees
Jun 23 - Jun 24
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,823 reviews)
"Beautiful property, beach access was terrific."
United States
Alison
The price is CA $406
CA $482 total
includes taxes & fees
Jun 27 - Jun 28
Napili Shores Maui by OUTRIGGER

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is CA $398
CA $472 total
includes taxes & fees
Jun 24 - Jun 25
Napili Sunset on the Beach

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1,141 reviews)
"Never a bad stay here!! "
United States
Michele
The price is CA $814
CA $966 total
includes taxes & fees
Jun 30 - Jul 1
The Westin Ka'anapali Ocean Resort Villas

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

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Lahaina
8.4 out of 10, Very good, (248 reviews)
"Great hotel and perfect location"
United States
Sevelina Georgieva
The price is CA $836
CA $993 total
includes taxes & fees
Jul 5 - Jul 6
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Kuleana Club - 504

Kuleana Club - 504
3.5 star property
Lahaina
Kuleana Club - 504

Honua Kai Hokulani Resort by KBM

Honua Kai Hokulani Resort by KBM
4.0 star property
Kaanapali
8.8 out of 10, Excellent, (24 reviews)
"Great beach location. Friendly staff. Pool had a slide, waterfalls and multiple hot tubs."
United States
stephanie
The price is CA $838
CA $1,924 total
includes taxes & fees
Jul 7 - Jul 8
Honua Kai Hokulani Resort by KBM

Whaler 518 Oceanview Studio Condo Condo by RedAwning

Whaler 518 Oceanview Studio Condo Condo by RedAwning
3.5 star property
Lahaina
The price is CA $410
CA $2,053 total
includes taxes & fees
Jun 23 - Jun 24
Whaler 518 Oceanview Studio Condo Condo by RedAwning

Oceanfront Maui Condo

Oceanfront Maui Condo
2.0 star property
Lainaina
The price is CA $264
CA $800 total
includes taxes & fees
Jul 6 - Jul 7
Oceanfront Maui Condo

Hale Mahina B304

Hale Mahina B304
3.0 star property
Lahaina
The price is CA $1,414
CA $1,678 total
includes taxes & fees
Jun 23 - Jun 24
Hale Mahina B304

Lanai & Steps to Beach! Stunning South Maui Condo

Lanai & Steps to Beach! Stunning South Maui Condo
3.5 star property
North Kihei
Lanai & Steps to Beach! Stunning South Maui Condo

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,983 reviews)
"Everything about this place was great!"
United States
Jag
The price is CA $725
CA $1,513 total
includes taxes & fees
Jul 5 - Jul 6
OUTRIGGER Honua Kai Resort & Spa

Kuleana Club - 511

Kuleana Club - 511
3.5 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"Room was very clean and well equipped. Nice pool and helpful staff in premise. "
United States
Baron
Kuleana Club - 511

The Westin Ka'anapali Ocean Resort Villas North

The Westin Ka'anapali Ocean Resort Villas North
4.0 star property
Lahaina
8.2 out of 10, Very good, (49 reviews)
"just another resort"
United States
Santosh
The price is CA $814
CA $966 total
includes taxes & fees
Jul 4 - Jul 5
The Westin Ka'anapali Ocean Resort Villas North

Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
Lahaina
8.8 out of 10, Excellent, (212 reviews)
"Marriott always offers top notch accommodations. Lahaina was on the beach, near shopping and restaurants."
United States
Mary S
The price is CA $814
CA $966 total
includes taxes & fees
Jul 9 - Jul 10
Marriott's Maui Ocean Club - Lahaina & Napili Towers

Kaanapali Shores #159 2 Bedroom Condo by RedAwning

Kaanapali Shores #159 2 Bedroom Condo by RedAwning
3.5 star property
Lahaina
The price is CA $413
CA $1,533 total
includes taxes & fees
Jul 3 - Jul 4
Kaanapali Shores #159 2 Bedroom Condo by RedAwning

Napili Point Resort by KBM

Napili Point Resort by KBM
4.0 star property
Napili-Honokowai
8.8 out of 10, Excellent, (21 reviews)
"Beautiful view of the ocean. They provided coffee filters and and some coffee for us and that was so nice (upon arrival part of the room)."
United States
Robert
The price is CA $3,243
CA $4,544 total
includes taxes & fees
Jul 9 - Jul 10
Napili Point Resort by KBM
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?

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!: 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 6 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.