Holiday Rentals in Upcountry Maui

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • 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, (4 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 €743
includes taxes & fees
20 Jan - 21 Jan
Haiku Hale - 3 Bedroom Maui Getaway!

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (192 reviews)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is €449
includes taxes & fees
1 Feb - 2 Feb
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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, (412 reviews)
"Great location"
United States
peter
Fisher's Hana Bay Hale, Across from Hana Bay

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Hana
10.0 out of 10, Exceptional, (188 reviews)
"Beautiful peaceful home. "
United States
Rebecca
The price is €517
includes taxes & fees
8 Feb - 9 Feb
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Hana
10.0 out of 10, Exceptional, (249 reviews)
"We loved staying here! It had all the amenities, was so comfortable and very easy for check in and check out. Perfect place for a quiet and relaxing stay in Hana. Also, SO close to the most gorgeous beach, only a two minute drive!"
United States
Kristi O.
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

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, (196 reviews)
"Very quiet safe place. "
Canada
Monica
The price is €381
includes taxes & fees
24 Jan - 25 Jan
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.4 out of 10, Exceptional, (147 reviews)
"Great space. Centrally located with easy proximity to food & groceries. Perfect for our needs. Comfy bed too. "
United States
Tracy A.
The price is €489
includes taxes & fees
26 Jan - 27 Jan
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hana
10.0 out of 10, Exceptional, (92 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is €489
includes taxes & fees
31 Jan - 1 Feb
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (111 reviews)
"Everything Good "
United States
Marc
The price is €518
includes taxes & fees
2 Feb - 3 Feb
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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, (75 reviews)
"We absolutely loved Hana and this location! It was peaceful and calm"
United States
Rebecca Z.
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (282 reviews)
"This was a great location, comfortable cute little cottage."
United States
Briana B.
Secluded cottage on Tropical flower farm

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, (122 reviews)
"A good place to stay "
United States
Xiaohong
The price is €403
includes taxes & fees
1 Feb - 2 Feb
Oceanview Condo in Hana-Let the ocean lull you to sleep

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647 reviews)
"Location was excellent"
United States
Polly
The price is €288
includes taxes & fees
20 Jan - 21 Jan
Napili Sunset on the Beach

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Kaʻeleku
9.8 out of 10, Exceptional, (77 reviews)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (3,953 reviews)
"Good resort"
United States
Sumit
The price is €329
includes taxes & fees
20 Jan - 21 Jan
Aston Kaanapali Shores

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (152 reviews)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is €216
includes taxes & fees
26 Jan - 27 Jan
Napili Village Hotel

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (141 reviews)
"We loved are quiet, peaceful stay in Hāna! So much fun! Beautiful property!"
United States
Justin
The price is €1,226
includes taxes & fees
29 Jan - 30 Jan
Hana Homestead by the Beach

Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (172 reviews)
"The house was perfect for us for the short time we stayed in Hana. The house was clean and the owner was friendly. The house is off the main road which made it quiet but still a short drive to Hana and the other wonderful sights on this side of the island."
United States
Steve &amp; Jamie T.
Beautiful Home in paradise!

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
North Kihei
10.0 out of 10, Exceptional, (131 reviews)
"Very nice condo Nice furniture Comfortable and friendly "
United States
John
The price is €319
includes taxes & fees
29 Jan - 30 Jan
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
North Kihei
10.0 out of 10, Exceptional, (34 reviews)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is €390
includes taxes & fees
23 Jan - 24 Jan
This remodeled condo earned "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 €327 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.