Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (30 reviews)
"The location was great, especially if you plan to see the whole island! Easy check in and check out. Clean place."
United States
Weronika
The price is NZ$593
includes taxes & fees
26 May - 27 May
Yonegan Maui Getaways - Haiku

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
8.6 out of 10, Excellent, (15 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
The price is NZ$806
includes taxes & fees
21 May - 22 May
Royal Lahaina Bungalows & Spa

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.4 out of 10, Very good, (25 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
The price is NZ$909
includes taxes & fees
21 May - 22 May
Signature Residences at Maui Banyan

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (2 reviews)
"Upscale and incredibly comfortable. This felt like a true upgrade from standard condos. The memory foam beds were heavenly, and the AC kept the place perfectly cool. We really appreciated the fast WiFi and having Netflix on the TV for relaxing evenings. Great gym onsite, too. We’ll definitely be back!"
United States
Sophie
The price is NZ$1,073
includes taxes & fees
10 June - 11 June
The Residences at Kamaole Sands Resort

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is NZ$929
includes taxes & fees
3 June - 4 June
The Ocean View Residence

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (909 reviews)
"Staff was amazing and nice! The GM is a huge Kansas City Chiefs fan. The property is beautiful and is a perfect walking distance for anything Kīhei/Wailea. Great TV channels as well. There are cute roosters, lizards and birds everywhere. Will be staying here again for sure! "
Canada
Ethan
The price is NZ$534
includes taxes & fees
28 May - 29 May
Aston Maui Hill

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NZ$1,228
includes taxes & fees
21 May - 22 May
Kuau Plaza Paia Condo with Parking

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,796 reviews)
"Everything was perfect! Will come back again"
United States
Alla
The price is NZ$482
includes taxes & fees
1 June - 2 June
Napili Shores Maui by OUTRIGGER

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (183 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is NZ$391
includes taxes & fees
19 May - 20 May
Napili Village Hotel

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is NZ$572
includes taxes & fees
20 May - 21 May
Napili Sunset on the Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (404 reviews)
"From check-in to check-out and all days in between the staff and property were wonderful.Clean, beautiful property located in the hub of Kaanapali Beach. Always a great place to stay."
United States
Ralph
The price is NZ$1,247
includes taxes & fees
19 May - 20 May
The Whaler Resort Kaanapali Beach

The Westin Ka'anapali Ocean Resort Villas North

The Westin Ka'anapali Ocean Resort Villas North
4.0 star property
Lahaina
8.2 out of 10, Very good, (47 reviews)
"Staff was great, rooms were clean, pools were warm. The ocean right outside the hotel is clean and allows you do do activities without leaving the area like snorkeling, swimming, boogie boarding, floating, etc)"
United States
Clinton
The price is NZ$925
includes taxes & fees
25 May - 26 May
The Westin Ka'anapali Ocean Resort Villas North

Kuleana Club - 210

Kuleana Club - 210
4.0 star property
Lahaina
8.0 out of 10, Very good, (2 reviews)
"We had an incredible stay at this beautiful property. The home was spacious and well-appointed, offering plenty of room for everyone to relax comfortably. Located in a gated community, we felt secure and appreciated the added sense of privacy and exclusivity. One of the absolute highlights was the private beach access—just a short walk away and never crowded. It felt like our own slice of paradise where we could unwind and enjoy the ocean without the usual tourist hustle. The landscaping and...
United States
Suresh
The price is NZ$1,156
includes taxes & fees
21 May - 22 May
Kuleana Club - 210

Napili Shores D229 Studio Bedroom Condo by RedAwning

Napili Shores D229 Studio Bedroom Condo by RedAwning
3.5 star property
Lahaina
8.0 out of 10, Very good, (1 review)
The price is NZ$2,123
includes taxes & fees
19 May - 20 May
Napili Shores D229 Studio Bedroom Condo by RedAwning

Kuleana Club - 701

Kuleana Club - 701
3.5 star property
Lahaina
Kuleana Club - 701

Kuleana Club - 712

Kuleana Club - 712
3.5 star property
Lahaina
The price is NZ$886
includes taxes & fees
22 May - 23 May
Kuleana Club - 712

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.2 out of 10, Wonderful, (32 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is NZ$810
includes taxes & fees
25 May - 26 May
Kihei Ali'i Kai Condos with Free Parking

Stunning South Maui Condo w/ Lanai by Beach!

Stunning South Maui Condo w/ Lanai by Beach!
3.5 star property
North Kihei
The price is NZ$658
includes taxes & fees
19 May - 20 May
Stunning South Maui Condo w/ Lanai by Beach!

The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
8.0 out of 10, Very good, (3 reviews)
"My stay was okay. "
United States
Rosalba
The price is NZ$1,458
includes taxes & fees
2 June - 3 June
The Kalama Residence

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Lahaina
8.4 out of 10, Very good, (248 reviews)
"Great hotel and perfect location"
United States
Sevelina Georgieva
The price is NZ$958
includes taxes & fees
31 May - 1 June
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
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.
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Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

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, 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 NZ$482 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.