Search Holiday Rentals in Upcountry Maui

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Top Holiday Rentals in Upcountry Maui

On the beach, white sand
Castle Napili Surf Beach Resort
3.5 star property
10.0 out of 10, Exceptional, (9)
"The bathroom and kitchen were generously stacked with everything we needed. The grounds were lovely and the unit very clean and comfortable. We had use of beach chairs and plenty of towels for the pool or beautiful beach. I highly recommend Castle Nāpili Surf Beach resort."
Castle Napili Surf Beach Resort
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
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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 £738
per night
27 May - 28 May
Aston at The Whaler on Kaanapali Beach
Sun deck
Napili Sunset on the Beach
2.5 star property
9.2 out of 10, Wonderful, (555)
"We have stayed at Napili Sunset before, it has been a great experience both times. Really enjoyed our time, and highly recommend. "
The price is £212
per night
17 May - 18 May
Napili Sunset on the 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)
"nice ,clean and roomy"
The price is £565
per night
5 Jun - 6 Jun
The Westin Nanea Ocean Villas, Ka'anapali
Outdoor pool, pool umbrellas
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (347)
"Absolutely thrilled with the cleanliness and quality of the room we stayed in. Would love to revisit if we get the chance to go to Maui again in the future. All staff was helpful and pleasant. Grounds and pool were kept immaculate. We thoroughly enjoyed our time here. "
Maui Schooner Resort
Exterior
Wailea Ekahi - CoralTree Residence Collection
3.0 star property
9.2 out of 10, Wonderful, (466)
"I would definitely recommend this property to other and would happily stay there again on a future trip to Maui"
Wailea Ekahi - CoralTree Residence Collection
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 £593
per night
4 Jun - 5 Jun
Aston Mahana at Kaanapali
Outdoor pool, pool loungers
Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (691)
"Great location, able to walk to the beach. Clean, peaceful, comfortable place to wind down after long day exploring. Would definitely stay there again if i return to Maui. "
Aston Maui Hill
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
On the beach
Napili Shores Maui by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, (1467)
"Absolutely wonderful! It’s not a fancy resort, but beautiful garden areas, we had a wonderful view from our room, and it is clean and quiet. Awesome beach access, great for swimming. Property is kid-friendly and I would absolutely come here again! "
Napili Shores Maui by OUTRIGGER
View from property
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (307)
"Beautiful grounds, right on the ocean, very centrally located to other places on the island "
Maui Sunset
Exterior
Maui Kamaole
3.5 star property
8.8 out of 10, Excellent, (789)
"We have a wonderful time at Maui Kamaole and would recommend to all our friends. We will defiantly be back! "
Maui Kamaole
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
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 £268
per night
3 Jun - 4 Jun
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2145)
"Beautiful grounds. Close o the pool and beach.! Castaway s great bar and restaurant. "
The price is £297
per night
21 May - 22 May
Aston Maui Kaanapali Villas
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (979)
"Great view of the ocean and a well appointed condo. Snack bar is not for everyone but the food was good. Centrally located to the bigger areas and the harbor. A good price point for a nice quiet vacation. We will return"
Sugar Beach Resort
2 outdoor pools, pool umbrellas
The Westin Ka'anapali Ocean Resort Villas
4.0 star property
8.6 out of 10, Excellent, (1048)
"As always an incredible experience We love this property"
The price is £483
per night
22 May - 23 May
The Westin Ka'anapali Ocean Resort Villas
Villa, 2 Bedrooms, Oceanfront (Bay 19G2 Gold 2.5 Bath) | View from room
Kapalua Villas Maui
4.0 star property
8.6 out of 10, Excellent, (891)
"The views and location are amazing! "
Kapalua Villas Maui
Don't see what you're looking for?
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.

Upcountry Maui Holiday Rental Travel Info

Holiday rentals
10
Popular accommodation
Upcountry Maui private holiday homes
International airport
Kahului, HI (OGG)

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, (1008)
"Staff were all nice and very friendly! Rooms clean and a lot of towels available. We all like it there."
The price is £276
per night
26 May - 27 May
Maui Coast Hotel
2 bars/lounges, 2 poolside bars, swim-up bar
Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
9.0 out of 10, Wonderful, (1001)
"Great place "
The price is £741
per night
23 May - 24 May
Grand Wailea Maui, A Waldorf Astoria Resort
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 £704
per night
26 May - 27 May
The Westin Maui Resort & Spa, Ka'anapali
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.

Everything you need to know about Upcountry Maui holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upcountry Maui holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Upcountry Maui holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upcountry Maui. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upcountry Maui holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upcountry Maui holiday rentals we have selected for you start as low as £268 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upcountry Maui rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upcountry Maui holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upcountry Maui. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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