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Top Holiday Rentals in Upcountry Maui

Exterior
The Whaler Resort Kaanapali Beach
4.0 star property
9.4 out of 10, Exceptional, (24)
"Direct access to the beach and the beach walk. Location with great views. Well Maintained. Front desk and employees friendly and helpful. We’ll be back. "
The Whaler Resort Kaanapali Beach
3 outdoor pools, pool loungers
Kaanapali Alii
4.0 star property
9.4 out of 10, Exceptional, (782)
"The staff were wonderful. They always helped us. "
Kaanapali Alii
View from room
Aston at The Whaler on Kaanapali Beach
4.0 star property
9.2 out of 10, Wonderful, (1393)
"We had a great stay. Only complaint was our room was right by Whalers Village side which was very noisy in the early am. Other than that the amenities were great, people were friendly and we really enjoyed our stay. "
The price is £618
includes taxes & fees
7 May - 8 May
Aston at The Whaler on Kaanapali Beach
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Outdoor pool, pool umbrellas
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (340)
"Place was nice. Staff are friendly. Highly recommend!"
Maui Schooner Resort
Sun deck
Napili Sunset on the Beach
2.5 star property
9.2 out of 10, Wonderful, (553)
"Close to the beach "
The price is £245
includes taxes & fees
5 May - 6 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, (417)
"Beautiful grounds, friendly staff, accommodation are accessible, clean, family friendly, everything you need for a family vacation"
The price is £548
includes taxes & fees
27 May - 28 May
The Westin Nanea Ocean Villas, Ka'anapali
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, (1462)
"Wonderful place 😊"
The price is £427
includes taxes & fees
6 May - 7 May
Aston Mahana at Kaanapali
Outdoor pool, pool loungers
Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (687)
"Very nice hotel!"
Aston Maui Hill
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2529)
"I loved everything about this resort. "
The price is £740
includes taxes & fees
24 May - 25 May
OUTRIGGER Honua Kai Resort & Spa
On the beach
Napili Shores Maui by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, (1464)
"Close to beach"
Napili Shores Maui by OUTRIGGER
Exterior
Maui Kamaole
3.5 star property
8.8 out of 10, Excellent, (789)
"Very nice place with a view. Clean with nice patio to relax on and have morning coffee. Staff in the office were very nice and helpful. They saved our trip because we booked a place that misrepresented their property and was very run down. We left and book here and it made a world of difference."
Maui Kamaole
View from property
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (305)
"Perfect place,Great location.Clean.Very good maintanance"
Maui Sunset
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, (2985)
"Great people And cleanliness "
The price is £279
includes taxes & fees
7 May - 8 May
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2138)
"Stuff was helpfhl and friendly, love coffee bar in the mornings"
The price is £284
includes taxes & fees
7 May - 8 May
Aston Maui Kaanapali Villas
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (975)
"ri9ght on the beach and had a pool too "
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 £488
includes taxes & fees
11 May - 12 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, (888)
"The view was amazing, very big showers the area was very quiet not noise at all, the privacy was unique! All the property was in excellent conditions we would recommend this for a very good time. "
Kapalua Villas Maui
View from property
Hono Koa Vacation Club
3.0 star property
8.6 out of 10, Excellent, (133)
"Donna greeted us when we arrived and from that moment on, it made for the greatest vacation we have ever had. Truly the most amazing vacation stay ever!!"
Hono Koa Vacation Club
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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.

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, pool umbrellas, pool loungers
Maui Coast Hotel
3.5 star property
9.2 out of 10, Wonderful, (1006)
"Nice older hotel. New one coming soon. Good bed and good a/c"
The price is £280
includes taxes & fees
5 May - 6 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, (1002)
"Potentially the most beautiful (semi all inclusive) resort in Maui. It was a treat and a delight to stay here. M"
The price is £758
includes taxes & fees
10 May - 11 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, (453)
"Our stay at Maui resort was exceptional and we would love to come back soon. Mahalo "
The price is £529
includes taxes & fees
11 May - 12 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 £245 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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