Holiday Rentals in Upcountry Maui

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Our top choices for Upcountry Maui holiday 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 €454
includes taxes & fees
10 Jun - 11 Jun
Aston Kaanapali Shores

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 €195
includes taxes & fees
9 Jun - 10 Jun
Napili Village Hotel

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 €430
includes taxes & fees
7 Jun - 8 Jun
Aston Maui Kaanapali Villas

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 €333
includes taxes & fees
7 Jul - 8 Jul
Napili Shores Maui by OUTRIGGER

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 €627
includes taxes & fees
23 Jun - 24 Jun
The Whaler Resort Kaanapali Beach

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 €588
includes taxes & fees
12 Jun - 13 Jun
The Westin Ka'anapali Ocean Resort Villas

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 €287
includes taxes & fees
14 Jun - 15 Jun
Napili Sunset on the Beach

Kuleana Club - 509

Kuleana Club - 509
3.5 star property
Lahaina
Kuleana Club - 509

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 €604
includes taxes & fees
20 Jun - 21 Jun
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (37 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is €457
includes taxes & fees
9 Jun - 10 Jun
Kihei Ali'i Kai Condos with Free Parking

Kuleana Club - 715

Kuleana Club - 715
3.5 star property
Lahaina
The price is €437
includes taxes & fees
13 Jun - 14 Jun
Kuleana Club - 715

Whaler 518 Oceanview Studio Condo Condo by RedAwning

Whaler 518 Oceanview Studio Condo Condo by RedAwning
3.5 star property
Lahaina
The price is €1,261
includes taxes & fees
7 Jun - 8 Jun
Whaler 518 Oceanview Studio Condo Condo by RedAwning

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 €404
includes taxes & fees
29 Jun - 30 Jun
Aston Maui Hill

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 €850
includes taxes & fees
7 Jul - 8 Jul
OUTRIGGER Honua Kai Resort & Spa

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 €276
includes taxes & fees
14 Jun - 15 Jun
Yonegan Maui Getaways - Haiku

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 €588
includes taxes & fees
12 Jun - 13 Jun
The Westin Ka'anapali Ocean Resort Villas North

Napili Point Resort by KBM

Napili Point Resort by KBM
4.0 star property
Napili-Honokowai
8.8 out of 10, Excellent, (20 reviews)
"Good place and location! Room has everything and host is responsive! Very close to the pool and steps away from snorkeling with plenty of turtles!"
United States
Vitaly
The price is €2,307
includes taxes & fees
7 Jun - 8 Jun
Napili Point Resort by KBM

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (2 reviews)
"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 €475
includes taxes & fees
7 Jun - 8 Jun
The Residences at Kamaole Sands Resort

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 €588
includes taxes & fees
18 Jun - 19 Jun
Marriott's Maui Ocean Club - Lahaina & Napili Towers

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 €478
includes taxes & fees
7 Jun - 8 Jun
Signature Residences at Maui Banyan
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

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 €333 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. 

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