Upcountry Maui Vacation Rentals

  • 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 vacation rentals

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,123 reviews)
"Amazing views and very spacious for family. Nice beach and pools!"
United States
Nicole
The price is NT$13,196
NT$16,600 total
includes taxes & fees
Jun 9 - Jun 10
Aston Kaanapali Shores

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (918 reviews)
"This is an excellent location from which to explore Maui. We would take the quick walk to the beach in the morning, explore the island in the afternoon and walk or drive to Kihei or Wailea for dinner. Pros: location, size of unit, kitchenette, free and ample parking, laundry, housekeeping, availability of host, clean pool, family atmosphere. As things get updated, it will be even better. We will be staying here again."
United States
Isabelle
The price is NT$12,441
NT$14,768 total
includes taxes & fees
Jun 29 - Jun 30
Aston Maui Hill

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,812 reviews)
"very nice would love to stay again just beautful."
United States
Steven L
The price is NT$8,289
NT$9,841 total
includes taxes & fees
Jun 13 - Jun 14
Napili Shores Maui by OUTRIGGER

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1,139 reviews)
"Never a bad stay here!! "
United States
Michele
The price is NT$18,094
NT$21,479 total
includes taxes & fees
Jun 19 - Jun 20
The Westin Ka'anapali Ocean Resort Villas

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (414 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 NT$9,610
NT$22,905 total
includes taxes & fees
Jun 7 - Jun 8
The Whaler Resort Kaanapali Beach

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (184 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is NT$5,996
NT$7,118 total
includes taxes & fees
Jun 9 - Jun 10
Napili Village Hotel

Kapalua Golf Villas Resort by KBM

Kapalua Golf Villas Resort by KBM
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (15 reviews)
"The property was in exquisite shape and the unit was very well kept. Great location! Just a short walk down a hill to beach access. Many restaurants nearby. Easy to drive to the unit."
United States
Clark
The price is NT$72,684
NT$101,040 total
includes taxes & fees
Jun 12 - Jun 13
Kapalua Golf Villas Resort by KBM

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (31 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is NT$4,445
NT$10,001 total
includes taxes & fees
Jun 28 - Jun 29
Yonegan Maui Getaways - Haiku

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Lahaina
8.4 out of 10, Very Good, (248 reviews)
"Great hotel and perfect location"
United States
Sevelina Georgieva
The price is NT$18,614
NT$22,097 total
includes taxes & fees
Jun 20 - Jun 21
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
8.2 out of 10, Very Good, (16 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
The price is NT$11,127
NT$14,879 total
includes taxes & fees
Jun 24 - Jun 25
Royal Lahaina Bungalows & Spa

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
Kuau Plaza Paia Condo with Parking

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,576 reviews)
"Great location for beach lovers and family vacation. "
United States
meryem
The price is NT$10,875
NT$15,711 total
includes taxes & fees
Jun 14 - Jun 15
Aston Maui Kaanapali Villas

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,976 reviews)
"Everything about this place was great!"
United States
Jag
The price is NT$13,135
NT$30,127 total
includes taxes & fees
Jun 10 - Jun 11
OUTRIGGER Honua Kai Resort & Spa

The Westin Ka'anapali Ocean Resort Villas North

The Westin Ka'anapali Ocean Resort Villas North
4.0 star property
Lahaina
8.2 out of 10, Very Good, (47 reviews)
"Staff was great, rooms were clean, pools were warm. The ocean right outside the hotel is clean and allows you do do activities without leaving the area like snorkeling, swimming, boogie boarding, floating, etc)"
United States
Clinton
The price is NT$18,094
NT$21,479 total
includes taxes & fees
Jun 19 - Jun 20
The Westin Ka'anapali Ocean Resort Villas North

Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning

Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning
3.5 star property
Lahaina
The price is NT$17,908
NT$67,703 total
includes taxes & fees
Jun 8 - Jun 9
Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning

Kapalua Ridge Villas Resort by KBM

Kapalua Ridge Villas Resort by KBM
4.5 star property
Lahaina
9.8 out of 10, Exceptional, (8 reviews)
"Clean and spacious. Beautiful ocean view "
United States
Shiqi
The price is NT$53,042
NT$83,642 total
includes taxes & fees
Jun 7 - Jun 8
Kapalua Ridge Villas Resort by KBM

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (26 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 NT$2,056
NT$17,467 total
includes taxes & fees
Jun 7 - Jun 8
Signature Residences at Maui Banyan

Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
Lahaina
8.8 out of 10, Excellent, (212 reviews)
"Marriott always offers top notch accommodations. Lahaina was on the beach, near shopping and restaurants."
United States
Mary S
The price is NT$18,110
NT$21,498 total
includes taxes & fees
Jun 20 - Jun 21
Marriott's Maui Ocean Club - Lahaina & Napili Towers

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is NT$8,848
NT$10,503 total
includes taxes & fees
Jun 18 - Jun 19
Napili Sunset on the Beach

Hale Mahina B304

Hale Mahina B304
3.0 star property
Lahaina
The price is NT$31,436
NT$37,318 total
includes taxes & fees
Jun 12 - Jun 13
Hale Mahina B304
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

Search for holiday rentals in Upcountry Maui on Expedia! You can easily find your home rentals, villas, holiday apartments in Upcountry Maui using one of the methods below:

  • View our selection of featured holiday rentals in Upcountry Maui
  • Use the map to find apartments and other holiday homes in the Upcountry Maui neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upcountry Maui while they last

Look no further and take a look at our great range of rental properties in Upcountry Maui!

Explore a world of travel with Expedia