Upcountry Maui Holiday Rentals

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Holiday Rentals in Upcountry Maui

Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3012)
"Beautiful experience "
The price is NZ$536
per night
3 Jun - 4 Jun
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2162)
"The property is in a great location it’s just a little bit outdated , the place I mean. In spite of my opinion I would go for a second time. Maybe a different time of the year."
The price is NZ$536
per night
31 May - 1 Jun
Aston Maui Kaanapali Villas
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2535)
"We went to the Honua Kai with our 3-year-old daughter as a recommendation from a friend who had gone earlier in the year with their one-year-old. We went for the ability to have washer-dryer, kitchenette, pools that were family-friendly, and an on-site store and restaurant. It lived up to our requirements with regards to everything. I also used the gym which was adequate for what I used it for (primarily treadmill running - when I didn't run on the beach, that is). Would recommend!"
The price is NZ$1,334
per night
12 Jun - 13 Jun
OUTRIGGER Honua Kai Resort & Spa
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Standard Room, 1 Bedroom | Living area
Kahana Beach Vacation Club
3.0 star property
8.2 out of 10, Very good, (542)
"Probably one of the cleanest rooms I’ve stayed in. The balcony directly faced the ocean with Molokai in full view."
Kahana Beach Vacation Club
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
Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1477)
"The Aston Mahana at Kaanapali Shores was superb! Every room has an ocean view and ours did not disappoint. Aside from the minor snag with getting a rental vehicle on the first day of our trip, everything is within walking distance and we made it work with a few Ubers and public transportation. Hotel staff are super friendly and they were very accommodating with anything needed. Highly recommend! "
The price is NZ$1,008
per night
2 Jun - 3 Jun
Aston Mahana at Kaanapali
Suite, 2 Bedrooms | Living area
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very good, (619)
"Nice and clean. Great value for the price "
Maui Beach Vacation Club
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (982)
"I liked this place because it was centrally located on the island, on the beach, nice view, spacious and clean."
Sugar Beach Resort
Suite, 1 Bedroom
The Gardens at West Maui
3.0 star property
8.4 out of 10, Very good, (377)
"We loved staying here!!! The best location- walkable to Napili and Kapalua. Clean, nice pool and hot tub. We will definitely be back!!"
The Gardens at West Maui
On the beach
Napili Shores Maui by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, (1473)
"The staff was wonderful!! Clean and beautiful!!"
Napili Shores Maui by OUTRIGGER
Outdoor pool, pool loungers
Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (696)
"It was a safe area, it was central to our needs. Easy Parking"
Aston Maui Hill
Outdoor pool
Aston at Papakea Resort
3.0 star property
8.2 out of 10, Very good, (1330)
"nice "
Aston at Papakea Resort
3 outdoor pools, pool loungers
Kaanapali Alii
4.0 star property
9.4 out of 10, Exceptional, (788)
"Loved this property from beginning to end. So clean and spacious. Personnel was super friendly and helpful. We had one issue with a drain and it was fixed w/in the hour. You are near everything...beach, restaurants and Whalers shopping center. Loved the pool area as well. Lots of chairs and lots of tables if you want to eat near the pool while looking over at the ocean. I have stayed 6x at different resorts on Kaanapali and this is in my top 2. We were sad to leave, great experience. "
Kaanapali Alii
View from room
Aston at The Whaler on Kaanapali Beach
4.0 star property
9.2 out of 10, Wonderful, (1402)
"We really enjoyed staying at the Whaler! It's very convenient in terms of beach access, shopping, and a veriety of restaraunts. The concierge was very helpful in booking trips and the staff was very friendly! Our condo specifically could use new pillows as they were old and flat. Otherwise, we enjoyed staying at the Whaler and would recommend it to friends. "
The price is NZ$1,447
per night
30 May - 31 May
Aston at The Whaler on Kaanapali Beach
Aerial view
Maui Banyan Vacation Club
3.0 star property
8.0 out of 10, Very good, (288)
"Everything was close to us enjoyed our stay planning a second trip soon "
Maui Banyan Vacation Club
Outdoor pool
Sands of Kahana
3.0 star property
8.2 out of 10, Very good, (377)
"Very close to beach and clean. Kitchen had everything I needed. Safeway grocery store is about 10 minutes drive. Location is a bit remote to travel and see the other half of the island."
Sands of Kahana
2 outdoor pools, pool umbrellas
The Westin Ka'anapali Ocean Resort Villas
4.0 star property
8.6 out of 10, Excellent, (1050)
"Perfect stay!"
The price is NZ$1,041
per night
3 Jun - 4 Jun
The Westin Ka'anapali Ocean Resort Villas
View from property
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (313)
"The condo is clean and has an ocean view. It overlooks the pool and a beautiful lawn area. The location is just down the street from restaurants, shopping and beaches."
Maui Sunset
On the beach, white sand
Castle Napili Surf Beach Resort
3.5 star property
10.0 out of 10, Exceptional, (10)
"The location is far out from other sites on Maui so we spent more time driving than we would have liked, yet the condo was perfect, and Napili bay is wonderful."
Castle Napili Surf Beach Resort
Exterior
Maui Kamaole
3.5 star property
8.8 out of 10, Excellent, (793)
"We enjoyed our stay very pleasant , clean and everything we needed was available thank you would definetl"
Maui Kamaole
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See all available properties in Upcountry Maui
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 Upcountry Maui you may be interested in

Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers
Maui Coast Hotel
3.5 star property
9.2 out of 10, Wonderful, (1002)
"We went with our 2 children. The hotel was clean and close to beaches and shopping. The room was clean and we felt safe there. The view from the balcony was beautiful. The room was cool and quiet. We really enjoyed our stay there and I highly recommend it! "
The price is NZ$508
per night
1 Jun - 2 Jun
Maui Coast Hotel
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3012)
"Beautiful experience "
The price is NZ$536
per night
3 Jun - 4 Jun
Aston Kaanapali Shores
Outdoor pool
Hilton Vacation Club Ka'anapali Beach Maui
4.0 star property
8.8 out of 10, Excellent, (1004)
"Overall good although a bit difficult as far as direction to the place. "
The price is NZ$535
per night
29 May - 30 May
Hilton Vacation Club Ka'anapali Beach Maui
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 Upcountry Maui 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 Upcountry Maui. 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 Upcountry Maui. Seeing all the best attractions is bound to make you fall in love with Upcountry Maui. 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 Upcountry Maui short-term rentals, that won’t be hard to do.

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