Kaanapali Holiday Rentals

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Holiday Rentals in Kaanapali

Pool
TOP FLOOR - STUNNING OCEAN VIEWS - RENOVATED UNIT - KAANAPALI WELCOMES YOU!!!
10.0 out of 10, Exceptional, (104)
"This property is exactly what was described. Lisa is amazing to communicate with. We’ve been to the resort multiple times, but this condo was by far the best. "
The price is NZ$1,005
includes taxes & fees
10 Jun - 11 Jun
TOP FLOOR - STUNNING OCEAN VIEWS - RENOVATED UNIT - KAANAPALI WELCOMES YOU!!!
Outdoor pool, a heated pool
Awesome Ocean View-Upgraded Penthouse Jr Suite at Kaanapali Shores-Unit 934
10.0 out of 10, Exceptional, (36)
"Lived my stay. Great room, the resort is very nice and well kept. Not as busy as the bigger resorts which was exactly what I was looking for. Would recommend it to anyone."
Awesome Ocean View-Upgraded Penthouse Jr Suite at Kaanapali Shores-Unit 934
A heated pool
Maui Resort Rentals: Honua Kai Konea 613 - Upgraded 6th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan
10.0 out of 10, Exceptional, (49)
"The unit was exactly as pictured. Amazing ocean views and lanai. Very clean. The Honua Kai was everything we needed. Great pool for the kids with a little water slide. Easy beach access. Duke’s poolside service for food and drinks. Would definitely stay here again."
The price is NZ$2,415
includes taxes & fees
8 Jun - 9 Jun
Maui Resort Rentals: Honua Kai Konea 613 - Upgraded 6th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan
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On the beach, sun-loungers, beach towels
DIRECT OCEANFRONT UNIT May 19-23 $395 Special 3Bedrm 3Bathrm Updates Equipped
9.8 out of 10, Exceptional, (156)
"Beautiful location and accommodations sum up our experience! The lanai view of whales, dolphins, and sea turtles was just amazing- we spent a lot of time enjoying the wildlife. The condo was comfortable and the layout worked well for our group --everyone had their own space and we appreciated the convenience of having a washer and dryer. Janet was very responsive to a slight issue we had and it was fixed without any problems the next day. We would love to stay here again in the future!"
DIRECT OCEANFRONT UNIT May 19-23 $395 Special 3Bedrm 3Bathrm Updates Equipped
Pool
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
9.8 out of 10, Exceptional, (128)
"The house and location were perfect for our family of 10. The neighborhood was quiet and a very short drive or 10 min walk to the beach. There was ample public parking next to the beach which was excellent for snorkelling. The pool was ideal for our 4 grandchildren and the house was beautiful and exactly as shown in the VRBO web site. Daniel was an excellent host and very responsive. We shall definitely return there"
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Property grounds
Direct Ocean Front~Kaanapali Beach~West Maui Paradise is Open and Welcomes You!
9.8 out of 10, Exceptional, (117)
"This was the perfect place to stay. Great views from the 6th floor, so much whale watching and turtle watching from the balcony. Beautiful starry skies at night and sunset views were breathtaking. So close to great food options and this building felt much less touristy and busy than others nearby. A great relaxing place with wonderfully thought out tools and accessories in the room! Highly recommend."
The price is NZ$773
includes taxes & fees
23 May - 24 May
Direct Ocean Front~Kaanapali Beach~West Maui Paradise is Open and Welcomes You!
Flat-screen TV
MK 308 Kaanapali OceanFront Condo w AC Pool
9.8 out of 10, Exceptional, (24)
"This was our 10th trip to Maui, but first at the Maui Kai. Beautiful condo, excellent location. We'll be back."
MK 308 Kaanapali OceanFront Condo w AC Pool
Outdoor dining
EL K203 2BD Condo w AC Pool Beach Cabana
9.6 out of 10, Exceptional, (49)
"Everything we needed for a great stay + snorkel gear was clutch!"
EL K203 2BD Condo w AC Pool Beach Cabana
Beach/ocean view
Relax and Enjoy Spectacular Oceanfront Views!
9.6 out of 10, Exceptional, (126)
"We loved our stay here, the condo is so nice and comfortable and the views are absolutely beautiful. Neal was very kind and helpful throughout the booking process and I would definitely stay here again!"
Relax and Enjoy Spectacular Oceanfront Views!
Exterior
The Whaler Resort Kaanapali Beach
4.0 star property
9.4 out of 10, Exceptional, (27)
"Great 2 bedroom condo. Spacious and very clean. Walkable to many restaurants including Whalers village which is right next door. 2 drawbacks : shower temperature was off and hard to adjust, shower was cold for at least 5 min before becoming warm and a very loud noise was always present coming from the generators in whalers village. Our balcony was on that side and it took away from the experience of just sitting outside. Recommend u get condo unit on the opposite side. But otherwise truly a...
The Whaler Resort Kaanapali Beach
3 outdoor pools, pool loungers
Kaanapali Alii
4.0 star property
9.4 out of 10, Exceptional, (786)
"The beach in front of the complex is beautiful. I would be cautious of expectations when it comes to the rooms. We were originally placed in a unit that hadn’t been updated in a long time. It looked nothing like the photos. A lot of carpet and heavy curtains (think 80’s). It is not great for someone that has allergies. We called to ask if we could be moved and they did accommodate us. The second unit was much better. The tennis courts were fun but very hot. "
Kaanapali Alii
View from room
Aston at The Whaler on Kaanapali Beach
4.0 star property
9.2 out of 10, Wonderful, (1398)
"The property is kept immaculate, just beautiful to walk around. Safe and quiet."
The price is NZ$1,517
includes taxes & fees
28 May - 29 May
Aston at The Whaler on Kaanapali Beach
2 outdoor pools, pool cabanas (surcharge), pool umbrellas
The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
9.2 out of 10, Wonderful, (420)
"Great place to stay with or without kids. Wonderful pool, awesome beach and professional staff. Of property food and grocery options too. Thos Westin is definitely on our revisit list if we come back to Kaanapali. "
The price is NZ$1,170
includes taxes & fees
4 Jun - 5 Jun
The Westin Nanea Ocean Villas, Ka'anapali
Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1469)
"Very nice and very well taking care of "
The price is NZ$1,229
includes taxes & fees
4 Jun - 5 Jun
Aston Mahana at Kaanapali
Basic Room, 1 Bedroom (Corner, Specific Unit May Vary) | Balcony view
Maui Kai
3.0 star property
9.0 out of 10, Wonderful, (391)
"Love love love this property. They have thought of everything. Why did I even need to pack anything?Room was excellent. Right on the beach. Staff was always friendly and willing to go out of their way to help. Check in after hours was a breeze. Cool pool area we never used. Parking was always available no matter when we got back and free. Nice convenient area. Food truck courtyard looked interesting but never could find the entrance will definitely stay here again"
Maui Kai
Beach/ocean view
Waterfront Resort Escape with Shared Pool, Hot Tub, Putting Green & Tennis
9.0 out of 10, Wonderful, (55)
"We enjoy the location of the Papakea Resort and have stayed there a few times. We enjoyed our stay. The living area was comfortable and clean. There were several beach items (chairs, umbrellas etc) available for our use. The bathroom, specifically the shower area, was a bit dingy and in need of an update. Overall, we were happy with the condo and our stay was a good one."
Waterfront Resort Escape with Shared Pool, Hot Tub, Putting Green & Tennis
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2531)
"I loved everything about this resort. "
OUTRIGGER Honua Kai Resort & Spa
Outdoor pool, pool umbrellas, pool loungers
AEI at The Mahana Kaanapali Resort
4.0 star property
8.8 out of 10, Excellent, (206)
"Honeymooners first time in Maui, we loved this hotel. In the touristy North-west section of Maui but right on the beach (beautiful sunsets), facility amenities were exactly what we were hoping for. Clean site and rooms, spacious room with full kitchen and living room and a washer/dryer in-unit. Concierge service was excellent at helping us book the tours/events we wanted despite short notice. Could have benefitted from more information about the facility at check-in, did not realize we had...
AEI at The Mahana Kaanapali Resort
Pool
OCEANVIEW Studio Condo at Kaanapali Shores Resort - Unit 742
8.8 out of 10, Excellent, (86)
"Great property over all! Only a few issues we had, the shower water only works at certain points and you must turn it a few times before it will come out hot. There’s lots of dead spots. The AC kicks in really hard during the day and then during the night shuts off so you wake up really hot. Over all tho we would stay again. The pools are great and you can walk to the beach. The room it’s self met our needs so we were happy "
OCEANVIEW Studio Condo at Kaanapali Shores Resort - Unit 742
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2998)
"Amazing views and right on the beach and pools were never packed "
The price is NZ$555
includes taxes & fees
27 May - 28 May
Aston Kaanapali Shores
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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.

Other types of properties in Kaanapali you may be interested in

Terrace/patio
The Westin Maui Resort & Spa, Ka'anapali
4.0 star property
8.8 out of 10, Excellent, (456)
"Great Hotel "
The price is NZ$1,458
includes taxes & fees
26 May - 27 May
The Westin Maui Resort & Spa, Ka'anapali
Outdoor pool
Hilton Vacation Club Ka'anapali Beach Maui
4.0 star property
8.8 out of 10, Excellent, (1007)
"We had a great time in Maii"
The price is NZ$474
includes taxes & fees
24 May - 25 May
Hilton Vacation Club Ka'anapali Beach Maui
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2998)
"Amazing views and right on the beach and pools were never packed "
The price is NZ$555
includes taxes & fees
27 May - 28 May
Aston Kaanapali Shores
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kaanapali holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kaanapali. 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 Kaanapali. Seeing all the best attractions is bound to make you fall in love with Kaanapali. Who knows, you may even be tempted to extend your 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 holiday 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 Kaanapali short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Kaanapali?

Yes, there are holiday rentals in Kaanapali close to West Maui Parasail, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Kaanapali speak highly of the array of shops and relaxing spas. Make sure to also enjoy the scenic seaside and top-notch restaurants during your holiday.

What are some of the best holiday rentals that Kaanapali has to offer?

Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach: This highly rated holiday home rental in Kaanapali is located in the city centre, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Kaanapali?

With 133 Expedia holiday rentals, you're guaranteed to find just the right place for your Kaanapali stay.

What can I see and do in Kaanapali?

Cultural attractions include Drums of the Pacific Lū‘au and Whalers Village Museum, whereas Kaanapali Beach and Kahekili Beach are a couple of picturesque spots to enjoy the outdoors. Black Rock and Whalers Village are other places to visit while you're in town.

What are holiday rentals like in Kaanapali?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kaanapali. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.

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