Search Vacation Homes in Upcountry Maui

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Upcountry Maui

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

Makawao
10.0 out of 10, Exceptional, (70)
"There is absolutely nothing we could think of that was missing from our week at Banyon Tree! The property is beautiful, lovingly maintained, and made this our best trip to Hawaii ever!! Actually, our best-ever family vacation! Plenty of room for swimming, playing Capture the Flag, enjoying family dinners, playing card and table games, and just hanging out. We enjoyed seeing the turtles at Ho’okepa Beach, playing in the river at Íao State Park, and shopping local markets. Comfortable island...
United States
Sheridan B.
The price is AED 5,273
AED 10,268 total
includes taxes & fees
19 Nov - 20 Nov
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

Haiku
The price is AED 1,947
AED 4,740 total
includes taxes & fees
23 Nov - 24 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku
10.0 out of 10, Exceptional, (4)
"The neighborhood is a nice quiet area, with shops & places to eat within a minute walk. The driveway is a bit tricky, but opens up to a beautiful property with plenty of outdoor space. The house itself was very clean & neat, and the rooms all fit our needs. We only stayed one night but wish we could have stayed a week! I would highly recommend this property to anyone looking to stay off the beaten path but still be able to see everything you want!"
United States
Nate G.
The price is AED 1,815
AED 3,632 total
includes taxes & fees
18 Nov - 19 Nov
Haiku Hale - 3 Bedroom Maui Getaway!

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

Hana
9.6 out of 10, Exceptional, (408)
"Nice space with a good location. Comfy beds. "
United States
Dannielle P.
The price is AED 639
AED 1,308 total
includes taxes & fees
5 Dec - 6 Dec
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

Kahului
9.6 out of 10, Exceptional, (408)
"We only stayed one night but it was fantastic, clean and cozy! Check in was super simple and we were able to get in and out quickly to enjoy the rest of our trip."
United States
Jarah A.
The price is AED 716
AED 1,465 total
includes taxes & fees
17 Dec - 18 Dec
Fisher's Hana Bay Hale, Across from Hana Bay

Yonegan Maui Getaways - Haiku

3.0 star property
Haiku
9.2 out of 10, Wonderful, (9)
"Loved having the hot tub to come home to!!"
United States
Pedro
The price is AED 450
AED 894 total
includes taxes & fees
18 Nov - 19 Nov
Yonegan Maui Getaways - Haiku

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

Hana
9.2 out of 10, Wonderful, (145)
"We liked the flat very much. Clean, cosy, like described."
Germany
Petra W.
The price is AED 790
AED 1,821 total
includes taxes & fees
23 Nov - 24 Nov
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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

Hana
9.8 out of 10, Exceptional, (235)
"Great place to stay if you are looking to get away from it all. "
United States
Jacques C.
The price is AED 1,074
AED 2,268 total
includes taxes & fees
18 Nov - 19 Nov
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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

Hana
9.8 out of 10, Exceptional, (76)
"We had a very relaxing time at this property! Such a beautiful place. We will definitely stay again. "
United States
Elizabeth C.
The price is AED 2,016
AED 3,634 total
includes taxes & fees
18 Nov - 19 Nov
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Hana Homestead by the Beach

Hana
9.8 out of 10, Exceptional, (136)
"The view from this house is absolutely amazing!! It overlooks Hana bay and the lighthouse. You can literally sit in the hot tub on the front porch and watch the sunset over the bay!"
United States
Sarah B.
The price is AED 1,851
AED 4,639 total
includes taxes & fees
15 Dec - 16 Dec
Hana Homestead by the Beach

New! The Aloha Cottage in Puamana, Maui Hawaii

Lahaina
9.8 out of 10, Exceptional, (86)
"Loved our stay at the Aloha Cottage. Property was clean and neat. Kitchen was well stocked which made cooking for the kids easy. Loved the outdoor lanai. Great spot for families and kids. Easy close beach access, but also easy drive to stores and restaurants in Lahaina. Nearby beaches were also great. Would definitely stay again. "
United States
Alexandra M.
The price is AED 971
AED 3,201 total
includes taxes & fees
18 Nov - 19 Nov
New! The Aloha Cottage in Puamana, Maui Hawaii

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

North Kihei
9.8 out of 10, Exceptional, (109)
"The property was clean, well maintained, and in a sweet, quiet neighborhood-a perfect home base for lots of day trips around Maui with tons of toys for beach-going. We hope to visit again! And a beautiful backyard and amenities!"
United States
Rachel C.
The price is AED 422
AED 1,905 total
includes taxes & fees
30 Nov - 1 Dec
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In

Paia
10.0 out of 10, Exceptional, (176)
"Was pleasant and quiet."
United States
Donovan W.
The price is AED 1,392
AED 3,517 total
includes taxes & fees
28 Nov - 29 Nov
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In

Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

South Kihei
9.2 out of 10, Wonderful, (60)
"Everything you need in the condo and enough beaches to try one every day!"
United States
Marco D.
The price is AED 547
AED 2,166 total
includes taxes & fees
18 Nov - 19 Nov
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

Oceanview Retreat in Puamana – Steps from the Beach & Surf

Lahaina
10.0 out of 10, Exceptional, (2)
"The condo was beautifully updated, very clean, and the furniture was comfortable. We loved the outdoor living space as well. We had everything we needed in the kitchen. The outdoor shower was a great extra! "
United States
Lauren F.
The price is AED 1,102
AED 4,158 total
includes taxes & fees
18 Nov - 19 Nov
Oceanview Retreat in Puamana – Steps from the Beach & Surf

NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

Lahaina
10.0 out of 10, Exceptional, (27)
"The house was perfect for our family of 5. We loved having beach items like chairs, umbrella, cooler, etc to use. Easy walk to the beach. The house had everything we needed! "
United States
Jen B.
The price is AED 915
AED 3,127 total
includes taxes & fees
18 Nov - 19 Nov
NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

Lahaina
10.0 out of 10, Exceptional, (3)
"This place was exactly what our family (3 adults and 2 toddlers) needed. It was immaculately clean, walkable to a very private beach, and had everything needed for our stay to be perfect (toys, beach gear, towels, kitchen necessities, etc). We would 100% rebook "
United States
Michael T.
The price is AED 1,314
AED 4,906 total
includes taxes & fees
18 Nov - 19 Nov
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

North Kihei
9.6 out of 10, Exceptional, (107)
"Overall, this house was in a great location, clean and beautiful accommodations and superb customer service. From the moment we arrived, I was impressed by the cleanliness. The host made a note to greet us when we got there. He then showed us throughout the house to make sure we knew where everything was and answer any questions we had. Throughout the week, he was available to offer suggestions, and we saw a lot of great local sights based on his recommendations. This was one of the best houses...
United States
Kristin S.
The price is AED 926
AED 3,670 total
includes taxes & fees
18 Nov - 19 Nov
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS

Lahaina
10.0 out of 10, Exceptional, (26)
"I looked around quite a bit and this property is everything they said it would be. Ocean right out the back door! I’m sure we will be back."
United States
Carl C.
The price is AED 1,653
AED 5,135 total
includes taxes & fees
24 Nov - 25 Nov
OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS

3BD WALK TO SANDY BEACH | Gated | LUXURY SPA FEEL

Lahaina
10.0 out of 10, Exceptional, (176)
"We had an amazing time in Maui. The house was clean, well stocked and in a great location. Communication was extremely easy and quick! Highly recommend!"
United States
Tina E.
The price is AED 1,646
AED 4,085 total
includes taxes & fees
7 Dec - 8 Dec
3BD WALK TO SANDY BEACH | Gated | LUXURY SPA FEEL
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