Upcountry Maui Vacation Rentals

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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, (3,988 reviews)
"Our room was great and the staff were always so friendly. Perfect place to stay for a good value. "
United States
Emily
The price is CA $518
CA $656 total
includes taxes & fees
Feb 21 - Feb 22
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,913 reviews)
"Wonderful vacation apot Everyone was amazing. "
United States
Michael
The price is CA $501
CA $1,225 total
includes taxes & fees
Feb 10 - Feb 11
OUTRIGGER Honua Kai Resort & Spa

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, (1,131 reviews)
"Staff friendly, great room and cleanliness. Amenties were excellent. "
United States
WILLIAM
The price is CA $677
CA $804 total
includes taxes & fees
Feb 22 - Feb 23
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, (353 reviews)
"We loved the location. Very clean & the staff was very nice "
United States
Pamela
The price is CA $491
CA $1,083 total
includes taxes & fees
Mar 9 - Mar 10
The Whaler Resort Kaanapali Beach

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,540 reviews)
"Nice clean room, nice staff and very quiet. "
United States
Marjie
The price is CA $499
CA $714 total
includes taxes & fees
Mar 1 - Mar 2
Aston Maui Kaanapali Villas

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (650 reviews)
"Great Hotel! Super clean! Has everything you need for perfect vacation!"
United States
Sergii
The price is CA $385
CA $456 total
includes taxes & fees
Feb 10 - Feb 11
Napili Sunset on the Beach

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
4.5 star property
South Kihei
8.0 out of 10, Very good, (11 reviews)
"Perfect location, clean room, and friendly staff! "
United States
Krystel
The price is CA $120
CA $825 total
includes taxes & fees
Feb 11 - Feb 12
Signature Residences at Maui Banyan

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (163 reviews)
"Amazing place to stay, loved it. "
United States
Jacqueline
The price is CA $332
CA $394 total
includes taxes & fees
Mar 3 - Mar 4
Napili Village Hotel

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is CA $209
CA $383 total
includes taxes & fees
Feb 15 - Feb 16
Yonegan Maui Getaways - Haiku

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
8.8 out of 10, Excellent, (23 reviews)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
The price is CA $284
CA $710 total
includes taxes & fees
Feb 17 - Feb 18
Kihei Ali'i Kai Condos with Free Parking

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, (238 reviews)
"Super clean room, staff was amazing will be back "
Canada
Carter Johannes
The price is CA $688
CA $817 total
includes taxes & fees
Feb 22 - Feb 23
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,750 reviews)
"Beautiful location, nice, clean rooms, friendly staff, and eating facilities on site!"
Canada
Larry Henry
The price is CA $475
CA $564 total
includes taxes & fees
Feb 10 - Feb 11
Napili Shores Maui by OUTRIGGER

The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (482 reviews)
"Wonderful place to stay. "
United States
Sharon Lynn
The price is CA $852
CA $1,012 total
includes taxes & fees
Feb 27 - Feb 28
The Westin Nanea Ocean Villas, Ka'anapali

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Upscale and incredibly comfortable. This felt like a true upgrade from standard condos. The memory foam beds were heavenly, and the AC kept the place perfectly cool. We really appreciated the fast WiFi and having Netflix on the TV for relaxing evenings. Great gym onsite, too. We’ll definitely be back!"
United States
Sophie
The price is CA $299
CA $1,207 total
includes taxes & fees
Mar 4 - Mar 5
The Residences at Kamaole Sands Resort

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (876 reviews)
"The location was great, staff provided clean towels and bedding daily. "
United States
Christine
The price is CA $628
CA $745 total
includes taxes & fees
Mar 8 - Mar 9
Aston Maui Hill

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.4 out of 10, Exceptional, (3 reviews)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is CA $566
CA $745 total
includes taxes & fees
Mar 2 - Mar 3
Royal Lahaina Bungalows & Spa

Kuleana Club - 504

Kuleana Club - 504
3.0 star property
Lahaina
The price is CA $474
CA $847 total
includes taxes & fees
Feb 20 - Feb 21
Kuleana Club - 504

Napili Shores D229 Studio Bedroom Condo by RedAwning

Napili Shores D229 Studio Bedroom Condo by RedAwning
3.5 star property
Lahaina
8.0 out of 10, Very good, (1 review)
The price is CA $398
CA $2,064 total
includes taxes & fees
Mar 8 - Mar 9
Napili Shores D229 Studio Bedroom Condo by RedAwning

Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.6 out of 10, Exceptional, (81 reviews)
"Amazing stayThis was our honeymoon. I would definitely come back again"
United States
Annette
The price is CA $2,563
CA $3,655 total
includes taxes & fees
Feb 26 - Feb 27
Honua Kai Konea Resort by KBM

Owner-Managed One Bedroom Condo

Owner-Managed One Bedroom Condo
2.5 star property
Lahaina
The price is CA $520
CA $726 total
includes taxes & fees
Feb 11 - Feb 12
Owner-Managed One Bedroom Condo
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.
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Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upcountry Maui. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.