A barren volcanic landscape with rugged terrain and distant mountains.

Holiday Rentals in Upcountry Maui

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Our top choices for Upcountry Maui holiday rentals

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is €906
includes taxes & fees
28 Jul - 29 Jul
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (6 reviews)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
United States
Linda S.
The price is €778
includes taxes & fees
25 Jul - 26 Jul
Haiku Hale - 3 Bedroom Maui Getaway!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Haiku
9.0 out of 10, Wonderful, (2 reviews)
"Very comfortable "
United States
Tanya N.
The price is €909
includes taxes & fees
28 Jul - 29 Jul
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (80 reviews)
"Great stay with Heleina and John! The property was spacious, very clean, and comfortable. Despite the terrible weather in Hawaii, they went above and beyond to accommodate us, even offering a complimentary extra night in case we got stuck. Truly thoughtful hosts. Would definitely stay again and I highly recommend! "
United States
Anna H.
The price is €2,572
includes taxes & fees
26 Jul - 27 Jul
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (946 reviews)
"Great stay. Grounds were nice and clean. Staff was friendly. I would stay there again."
United States
Douglas Paul Zwerner or Laura
The price is €309
includes taxes & fees
1 Aug - 2 Aug
Aston Maui Hill

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (520 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is €349
includes taxes & fees
24 Jul - 25 Jul
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Wailea Elua- CoralTree Residence Collection

Wailea Elua- CoralTree Residence Collection
3.5 star property
Wailea
9.6 out of 10, Exceptional, (257 reviews)
"Amazing trip"
United States
tammie
The price is €945
includes taxes & fees
16 Aug - 17 Aug
Wailea Elua- CoralTree Residence Collection

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,834 reviews)
"Perfect place to relax has everything you need you can stay in and cook for yourself or you can go to the restaurant plenty of options up the street perfect place to be in paradise"
United States
monica gene
The price is €216
includes taxes & fees
7 Aug - 8 Aug
Napili Shores Maui by OUTRIGGER

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (433 reviews)
"Great location! We enjoyed being right by Whaler’s Village with all the restaurants and shops. It’s also close to Black Rock which is great for snorkeling. We will be coming back for future Maui trips."
United States
Julie
The price is €605
includes taxes & fees
10 Aug - 11 Aug
The Whaler Resort Kaanapali Beach

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,193 reviews)
"We were very happy with our stay."
United States
Joni
The price is €252
includes taxes & fees
5 Aug - 6 Aug
Aston Kaanapali Shores

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (203 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is €293
includes taxes & fees
12 Aug - 13 Aug
Napili Village Hotel

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (460 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is €363
includes taxes & fees
24 Jul - 25 Jul
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (279 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
The price is €364
includes taxes & fees
31 Jul - 1 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (304 reviews)
The price is €365
includes taxes & fees
4 Aug - 5 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.2 out of 10, Wonderful, (147 reviews)
"Beautiful location. Quiet and relaxing."
United States
Frank A.
The price is €399
includes taxes & fees
27 Jul - 28 Jul
Oceanview Condo in Hana-Let the ocean lull you to sleep

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (213 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is €398
includes taxes & fees
31 Jul - 1 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection
4.0 star property
Wailea
9.4 out of 10, Exceptional, (116 reviews)
"Most beautiful view"
United States
Vesselina
The price is €1,058
includes taxes & fees
14 Aug - 15 Aug
Makena Surf - CoralTree Residence Collection

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (446 reviews)
"Great stay thanks! "
United States
Stephanie C.
Fisher's Hana Bay Hale, Across from Hana Bay

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (313 reviews)
"Kevin was a great host! Communication was prompt and he gave wonderful suggestions on places to eat, things to do.The condo was beautiful, very cozy and clean.We would definitely stay here again"
United States
Janet M.
The price is €369
includes taxes & fees
29 Jul - 30 Jul
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets

Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
Central Kihei
10.0 out of 10, Exceptional, (202 reviews)
"We loved this place! Was perfect for what we were needing:)"
United States
Alana C.
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
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, 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 €216 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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