Kaanapali Hillside Vacation Rentals from ￥21,643: Search Short-Term Rentals

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Vacation Rentals in Kaanapali Hillside

Enjoy ocean views from the large window in this serene bedroom with a comfortable bed and stylish decor.

"We had a great time at this VRBO! It was so clean and was the perfect lay out for our family. The beds were comfortable and the views were gorgeous! We will definitely be staying again. "

￥117,657 total

includes taxes & fees

Jul 13 - Jul 14

"We loved our stay! The place had everything the family needed for visiting the beach and the place was clean and comfortable. Would stay again! "

￥67,352 total

includes taxes & fees

Aug 2 - Aug 3

Enjoy breathtaking ocean views from this resort, surrounded by lush greenery and palm trees, with a pool and parking area on site.

"Clean, cozy and nicely designed. This condo has an amazing view and access to the beach and pool. Kitchen is well equipped, even has a milk warmer/frother which I appreciate so much as a lover of lattes. We'll happily stay here again on our next trip to Maui. "

￥107,131 total

includes taxes & fees

Jul 11 - Jul 12

Relax by the serene pool surrounded by lush tropical plants and a naturalistic rock formation.

￥84,234 total

includes taxes & fees

Jul 13 - Jul 14

Relax in a serene garden setting with a bench and a door leading to the laundry area.

"Place was great and would definitely stay again! There was a nice yard and a closet full of beach gear, chairs and coolers we made use of. Only thing that would have been better was if the hot tub was not on a timer that shuts off later at night. Great spot!!"

￥274,102 total

includes taxes & fees

Jul 15 - Jul 16

Experience the serene coastal landscape with turquoise sea, rugged coastline, and lush green vegetation.

"Quiet neighborhood setting. Nice backyard for relaxing. Well equipped with beach accessories including snorkel gear. Large whirlpool tub and comfortable bed. Be prepared for carrying luggage to second floor."

￥94,177 total

includes taxes & fees

Jul 28 - Jul 29

Relax in a serene garden setting with a bench and sheltered by a metal roof.

"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"

￥197,283 total

includes taxes & fees

Jul 15 - Jul 16

"We all loved it!"

￥102,014 total

includes taxes & fees

Aug 7 - Aug 8

￥80,392 total

includes taxes & fees

Aug 7 - Aug 8

Relax in a serene beach setting surrounded by lush greenery and palm trees, with access to the ocean.

￥102,466 total

includes taxes & fees

Aug 3 - Aug 4

Enjoy ocean views from the rooftop pool surrounded by palm trees and lush greenery.

￥91,583 total

includes taxes & fees

Aug 3 - Aug 4

Enjoy a serene beachside retreat with access to the ocean and lush surroundings.

"We greatly enjoyed our stay in this unit and on this property. The unit was exceptionally clean, well-maintained, and the kitchen was exceptional. The beds gave you the option of either a soft surface or a firm mattress. Excellent view from the lanai. And the snorkeling in Honokeana Bay was exceptional! Sea turtles galore! Will be back next year!"

￥73,514 total

includes taxes & fees

Jul 15 - Jul 16

￥102,817 total

includes taxes & fees

Aug 3 - Aug 4

￥127,760 total

includes taxes & fees

Aug 4 - Aug 5

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and coffee maker.

￥120,660 total

includes taxes & fees

Aug 3 - Aug 4

Relax by the tranquil pool surrounded by lush vegetation and palm trees, with a soothing waterfall feature and comfortable lounge seating.

"This resort is highly recommended, perfect location, perfect facilities for family with small kids and grandparents."

￥1,105,919 total

includes taxes & fees

Jul 27 - Jul 28

￥70,235 total

includes taxes & fees

Jul 16 - Jul 17

￥71,100 total

includes taxes & fees

Jul 16 - Jul 17

￥86,545 total

includes taxes & fees

Jul 17 - Jul 18

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Find out more about Kaanapali Hillside

Search for holiday rentals in Kaanapali Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Kaanapali Hillside using one of the methods below:

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Recent reviews of Kaanapali Hillside properties

5/5 Excellent

Little slice of paradise

"Great staff and great value."

A verified traveler stayed at Maui Seaside Hotel

Posted 22 hours ago

5/5 Excellent

"Had an amazing time at this resort. The staff was amazing, from front desk, restaurants, and valet. Beautiful, well manicured grounds and 24 hour pool. Appreciated that we could use the Hyatt Vacation Club next door as they too had an amazing pool and hot tubs. The towel distribution and return machines were very handy, wish all resorts had this system. While the beach right in front of the property is quite narrow, you can walk in either direction and the beach widens out. Great snorkeling right there, saw plenty of beautiful fish and turtles. Nice to have the laundry facilities on site. And lasty, the Swan breakfast buffet was delicious and a welcome addition! "

A verified traveler stayed at Hyatt Regency Maui Resort & Spa

Posted 2 days ago

5/5 Excellent

"We liked the quiet in the room. The workers were helpful and very pleasant to us. We enjoyed the morning breakfast with options that were similar to what we usually eat at home. I enjoyed the availability of the coffee next to the check in desk. The only thing that bothered us a little was the height of the bed. At our age and height, the bed was a little high to get in comfortably. We look forward to book this hotel the next time we go to Maui."

A verified traveler stayed at Hampton Inn & Suites Maui North Shore

Posted 2 days ago

5/5 Excellent

"Hotel is fantastic and pool and beach situation is hard to beat. Convenient to restaurants and shops at Whalers Village. Good service and room layout. Small downside is the outsourced towel operation at the pool - closes at 5 even though the pool is open until 8. And then the pool area isn’t cleaned up until the outsourced company comes back on duty in the AM. But that’s a fairly small complaint overall. Would definitely stay again. "

A verified traveler stayed at Sheraton Maui Resort & Spa

Posted 3 days ago

5/5 Excellent

"It’s all about Napili Bay it is so beautiful and stay at Napili Shores was simply wonderful. Stayed in a studio sized room with ocean view, definitely a bonus. All items for bathroom, kitchen or comfort are perfectly provided and well thought out. Pro tip, stop at Costco after landing at airport if they’re open for food, drinks and snacks. "

A verified traveler stayed at Napili Shores Maui by OUTRIGGER

Posted 3 days ago

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?

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool: Visitors like this Kaanapali Hillside vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Kaanapali Kai Course at Kaanapali Golf Resort 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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Kaanapali Hillside Vacation Rentals

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Vacation Rentals in Kaanapali Hillside

Charming Direct Oceanfront North Shore Beach House

Beautiful 3-bedroom townhome in Kihei

Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Menehune Shores 121: 2 BR, 2 BA Condominium in Kihei, Sleeps 4

Oceanfront Paradise in North Kihei

NB 210 Direct Ocean Views from this Napili Bay Studio Steps from the Sand Ocean

RK 616 Bright Blue Ocean Views and Sunsets from this Studio Condo in the heart of West Maui!

Oceanfront getaway with a furnished patio, views, pool, & high-speed WiFi

KS 826 Enjoy Ocean and Neighbor Island Views from this 1BD Kaanapali Shores Condo

KS 529 Oceanview 2BD Condo at Kaanapali Shores Steps to the Pools and Hot Tub!

KPL 34 North Kaanapali Hillside 2BD Condo with Ocean Views and Sunsets

Oceanfront - 2 Bedroom - Westin Kaanapali Ocean Resort Villas - Full Resort Access

Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N

Maui Ka’anapali Villas #C261: Studio garden view condo at Beach Front Resort on

Aston Maui Kaanapali Villas #260 - 2 Sleeping Areas, 2 Bathrooms, 4 Guests

Find out more about Kaanapali Hillside

Recent reviews of Kaanapali Hillside properties

Maui Seaside Hotel

Maui Beach Hotel

The Westin Maui Resort & Spa, Ka'anapali

Hyatt Regency Maui Resort & Spa

Hampton Inn & Suites Maui North Shore

Royal Lahaina Resort & Bungalows

Sheraton Maui Resort & Spa

Napili Shores Maui by OUTRIGGER

OUTRIGGER Kaanapali Beach Resort

Frequently asked questions