Search Vacation Homes in Upcountry Maui

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Vacation Homes in Upcountry Maui

Our top choices for Upcountry Maui vacation homes

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

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

10.0 out of 10, Exceptional, (68)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Haiku Hale - 3 Bedroom Maui Getaway!
Property grounds

Haiku Hale - 3 Bedroom Maui Getaway!

10.0 out of 10, Exceptional, (4)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
The price is SAR 1,854
SAR 3,674 total
includes taxes & fees
13 Sep - 14 Sep
Haiku Hale - 3 Bedroom Maui Getaway!
Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is SAR 423
SAR 870 total
includes taxes & fees
12 Oct - 13 Oct
Yonegan Maui Getaways - Haiku
Fisher's Hana Bay Hale, Across from Hana Bay
Beach towels

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (401)
"Wonderful property and a great place to stay in Hana"
The price is SAR 732
SAR 1,489 total
includes taxes & fees
8 Oct - 9 Oct
Fisher's Hana Bay Hale, Across from Hana Bay
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Beach towels

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

9.6 out of 10, Exceptional, (396)
"The property was excellent, highly recommend. "
The price is SAR 653
SAR 1,336 total
includes taxes & fees
8 Oct - 9 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Sun loungers, beach towels

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

9.4 out of 10, Exceptional, (143)
"We had a really nice stay at the Hana Bay View. The property had a really updated bathroom and good kitchen appliances. The covered deck was the best for winding down in the evening after all of our fun hiking and beach excursions! The AC in the bedrooms was a huge bonus. I highly recommend this place."
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!
Outdoor dining

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

9.8 out of 10, Exceptional, (229)
"Wonderful location!"
The price is SAR 1,126
SAR 2,354 total
includes taxes & fees
23 Sep - 24 Sep
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
Property grounds

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

9.8 out of 10, Exceptional, (76)
"Phenomenal property for your stay in Hana - especially for a large group "
The price is SAR 2,026
SAR 3,668 total
includes taxes & fees
15 Sep - 16 Sep
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Exterior

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

9.8 out of 10, Exceptional, (140)
"Wonderful property and so beautiful! "
The price is SAR 1,313
SAR 2,464 total
includes taxes & fees
14 Sep - 15 Sep
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood
Beach

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

The price is SAR 675
SAR 1,025 total
includes taxes & fees
21 Sep - 22 Sep
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood
Hana Homestead by the Beach
Fridge, microwave, oven, stovetop

Hana Homestead by the Beach

9.8 out of 10, Exceptional, (134)
"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "
The price is SAR 1,790
SAR 4,611 total
includes taxes & fees
21 Sep - 22 Sep
Hana Homestead by the Beach
Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach
A heated pool

Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach

Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach
Charming Direct Oceanfront North Shore Beach House
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Charming Direct Oceanfront North Shore Beach House

9.0 out of 10, Wonderful, (33)
"We had a great time at this VRBO! It was so clean and was the perfect lay out for our family. The beds were comfortable and the views were gorgeous! We will definitely be staying again. "
Charming Direct Oceanfront North Shore Beach House
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (173)
"We had a great time. The house was very well organized and equipped "
The price is SAR 1,572
SAR 3,836 total
includes taxes & fees
1 Oct - 2 Oct
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121
Pool

Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121

10.0 out of 10, Exceptional, (186)
"Our trip to Maui was enjoyable, but the condo really was ideal. We loved being on the ground floor and being able to walk off of the lanai to the beach. We were able to see sunsets and sunrises each day. Kihei beaches were close by and easy to access. There were plenty of fans and a great ocean breeze each evening that kept us cool. Will be back!!"
Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Property grounds

Oceanview Retreat in Puamana – Steps from the Beach & Surf

10.0 out of 10, Exceptional, (1)
"This property had everything you would want in a vacation home. Great location. We enjoyed the beach, community pool and grounds. The photos were exactly as pictured. We had a great time in your home. Thank you for hosting us."
The price is SAR 1,219
SAR 4,425 total
includes taxes & fees
13 Sep - 14 Sep
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home
Property grounds

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home
NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!
2 bedrooms, desk, iron/ironing board, travel crib

NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

10.0 out of 10, Exceptional, (26)
"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! "
NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach
Exterior

Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

10.0 out of 10, Exceptional, (7)
"Clean, cozy and nicely designed. This condo has an amazing view and access to the beach and pool. Kitchen is well equipped, even has a milk warmer/frother which I appreciate so much as a lover of lattes. We'll happily stay here again on our next trip to Maui. "
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach
Experience luxury in a spacious 900 sq ft condo in South Kihei, featuring 2 bedrooms with king beds
Interior

Experience luxury in a spacious 900 sq ft condo in South Kihei, featuring 2 bedrooms with king beds

Experience luxury in a spacious 900 sq ft condo in South Kihei, featuring 2 bedrooms with king beds
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
Sign in
Sign up, it's free

Top Upcountry Maui Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"everything clean professional upscale quiet close to shopping"
Theodore Aaron 5-night trip
Posted 16 hours ago
Aston Kaanapali Shores