Search Holiday Rentals in Upcountry Maui

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upcountry Maui holiday rentals

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (5 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 £652
includes taxes & fees
31 May - 1 Jun
Haiku Hale - 3 Bedroom Maui Getaway!

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, (77 reviews)
"What a great place for our extended family of 12! Plenty of room, and the kids really enjoyed the ping pong table, pool, and hot tub! Helaina was great and left us multiple treats including avocados from her tree!"
United States
Laura K.
The price is £2,348
includes taxes & fees
28 Jun - 29 Jun
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (57 reviews)
"Clean and quiet spot in Hana! A great base for exploring the road to Hana without having to do it all in a day."
United States
Paul John Van de
The price is £261
includes taxes & fees
2 Jun - 3 Jun
Stay in Hana #2

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (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 £386
includes taxes & fees
31 May - 1 Jun
Signature Residences at Maui Banyan

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (36 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is £315
includes taxes & fees
6 Jun - 7 Jun
Kihei Ali'i Kai Condos with Free Parking

Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana Town Center
9.8 out of 10, Exceptional, (238 reviews)
"Great location in Hana. Cozy and private. "
United States
Heather F.
The price is £394
includes taxes & fees
26 Jun - 27 Jun
Great location between Hana Town and Hamoa Beach, private, family-friendly

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.4 out of 10, Exceptional, (433 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
The price is £301
includes taxes & fees
22 Jun - 23 Jun
Fisher's Hana Bay Hale, Across from Hana Bay

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 £168
includes taxes & fees
31 May - 1 Jun
Napili Village Hotel

Relaxing home away from home- honeymoon friendly

Relaxing home away from home- honeymoon friendly
Hana
10.0 out of 10, Exceptional, (285 reviews)
"It was such a cute little place. Quite and charming with a spectacular view. Loved our stay here."
Canada
Marjorie
The price is £396
includes taxes & fees
1 Jun - 2 Jun
Relaxing home away from home- honeymoon friendly

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,804 reviews)
"Perfect place to stay, good location"
United States
Aurelia
The price is £209
includes taxes & fees
10 Jun - 11 Jun
Napili Shores Maui by OUTRIGGER

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, (208 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 £333
includes taxes & fees
31 May - 1 Jun
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (916 reviews)
"Front desk personal was friendly and helpful."
United States
hector
The price is £273
includes taxes & fees
25 Jun - 26 Jun
Aston Maui Hill

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Hana
10.0 out of 10, Exceptional, (256 reviews)
"Beautiful place."
United States
Jessica R.
The price is £443
includes taxes & fees
28 Jun - 29 Jun
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (411 reviews)
"We love staying at The Whaler Resort! I like that it’s right next to all the shops and restaurants at Whaler Village. It’s a really nice combination of hotel amenities and condo living. The staff is super friendly and the property is very well maintained. We’ll definitely be staying here again."
United States
Dustin
The price is £541
includes taxes & fees
30 May - 31 May
The Whaler Resort Kaanapali Beach

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"I love spending time here. This is such a wonderful place to stay if you want to get away. It was our 2nd time, and we loved every minute of it. Including the rain. Manager was very helpful. The house was stocked with everything you need. "
United States
Anonymous traveller
The price is £408
includes taxes & fees
11 Jun - 12 Jun
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (37 reviews)
"Everything was great."
United States
Bryan
The price is £239
includes taxes & fees
31 May - 1 Jun
Yonegan Maui Getaways - Haiku - Unit 6

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Kaʻeleku
9.8 out of 10, Exceptional, (246 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is £445
includes taxes & fees
31 May - 1 Jun
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (78 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is £379
includes taxes & fees
31 May - 1 Jun
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (118 reviews)
"Beautiful place to stay in Hana and super nice people. "
United States
Tanya L.
The price is £384
includes taxes & fees
31 May - 1 Jun
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (40 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is £328
includes taxes & fees
3 Jun - 4 Jun
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
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.
Save an average of 15% on thousands of hotels when you're signed in

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 £209 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.