A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Upcountry Maui vacation rentals

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
$283 nightly
The price is $308
Oct 6 - Oct 7
Total with taxes and fees
Yonegan Maui Getaways - Haiku
A resort with a swimming pool, palm trees, and ocean views.

2. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (983 reviews)
"The property was very welcoming and respectful. Love the swimming pool . We went in it every day. We meet a lot of people who has timeshares and respect their surroundings. Mahalo 🌺"
United States
Lisa
$276 nightly
The price is $328
Nov 4 - Nov 5
Total with taxes and fees
Aston Maui Hill
A modern kitchen with a large island, a dining area with a view, and a living room with a sofa and chairs.

3. Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (54 reviews)
"Absolutely an amazing place. Very nice, clean, comfortable. We stayed in B104 and it is a perfect spot to get in and out. Definitely come back again."
United States
Angeline
$423 nightly
The price is $502
Oct 17 - Oct 18
Total with taxes and fees
Kihei Ali'i Kai Condos with Free Parking
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

4. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (39 reviews)
"It was as good as a motel 6 bed was comfortable and my beach front condo as it was described was a room facing a mountain that you couldn’t see passed the forest of plants in front of back patio and the ac unit was very old and loud but served its purpose"
United States
Roark
$447 nightly
The price is $531
Oct 12 - Oct 13
Total with taxes and fees
Signature Residences at Maui Banyan
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

5. The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas"
United States
George Lucas
$500 nightly
The price is $593
Oct 7 - Oct 8
Total with taxes and fees
The Residences at Kamaole Sands Resort
A beach with clear blue water, rocky shore, and palm trees.

6. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
3.0 star property
Paia
$353 nightly
The price is $418
Oct 8 - Oct 9
Total with taxes and fees
Condo w/ Lanai at Beginning of Road to Hana!
A beach with clear blue water, a sandy shore, and palm trees.

7. The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
8.0 out of 10, Very good, (3 reviews)
"My stay was okay. "
United States
Rosalba
$711 nightly
The price is $845
Oct 6 - Oct 7
Total with taxes and fees
The Kalama Residence
A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

8. Grand Champions by KBM

Grand Champions by KBM
3.5 star property
Wailea
10.0 out of 10, Exceptional, (5 reviews)
"Clean everything great time great location! "
United States
Sean
$714 nightly
The price is $847
Oct 7 - Oct 8
Total with taxes and fees
Grand Champions by KBM
A beach with clear blue water, palm trees, and a resort in the background.

9. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (241 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
$192 nightly
The price is $228
Nov 3 - Nov 4
Total with taxes and fees
Napili Village Hotel
A tropical garden with a waterfall, lush greenery, and a gazebo.

10. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,356 reviews)
"Great Stay"
United States
Roopa Rani
$264 nightly
The price is $314
Oct 7 - Oct 8
Total with taxes and fees
Aston Kaanapali Shores
A view of a beach with palm trees and a sailboat on the water.

11. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (485 reviews)
"Great place"
United States
Alessio
$561 nightly
The price is $666
Oct 7 - Oct 8
Total with taxes and fees
The Whaler Resort Kaanapali Beach
A resort with multiple bungalow-style buildings, a swimming pool, and a beach.

12. Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
7.8 out of 10, Good, (27 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
$370 nightly
The price is $439
Nov 3 - Nov 4
Total with taxes and fees
Royal Lahaina Bungalows & Spa
A tropical beach scene with palm trees, a clear blue sky, and a view of the ocean.

13. Waiohuli Beach Hale Ocean View Condos with Parking

Waiohuli Beach Hale Ocean View Condos with Parking
3.0 star property
Central Kihei
9.8 out of 10, Exceptional, (6 reviews)
"Easy access to the beach, nice kitchen, view of the water"
United States
Phillip J
$460 nightly
The price is $546
Oct 6 - Oct 7
Total with taxes and fees
Waiohuli Beach Hale Ocean View Condos with Parking
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

14. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,891 reviews)
"Great property"
United States
Shawn
$224 nightly
The price is $266
Oct 25 - Oct 26
Total with taxes and fees
Napili Shores Maui by OUTRIGGER
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

15. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,643 reviews)
"Great place will stay again!"
United States
Joseph
$295 nightly
The price is $351
Nov 1 - Nov 2
Total with taxes and fees
Aston Maui Kaanapali Villas
A beach with a building on the left, a rocky breakwater, and a clear blue sky.

16. Lanai & Steps to Beach! Stunning South Maui Condo

Lanai & Steps to Beach! Stunning South Maui Condo
3.5 star property
North Kihei
$420 nightly
The price is $498
Oct 15 - Oct 16
Total with taxes and fees
Lanai & Steps to Beach! Stunning South Maui Condo
A beach view with lounge chairs and a clear sky.

17. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
$300 nightly
The price is $356
Nov 3 - Nov 4
Total with taxes and fees
Napili Sunset on the Beach
A resort pool area with a hot tub, lounge chairs, and palm trees.

18. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
$1,336 nightly
The price is $1,586
Oct 7 - Oct 8
Total with taxes and fees
Villa, Garden View, 2-bedroom
A patio with a round table and two chairs, overlooking a grassy area with a view of the ocean and a clear sky.

19. Kuleana Club - 608

Kuleana Club - 608
3.5 star property
Lahaina
Kuleana Club - 608
A resort with a pool, palm trees, and a night scene with fire torches.

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

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (254 reviews)
"Great property very close to everything"
United States
Carroll M
$511 nightly
The price is $607
Oct 18 - Oct 19
Total with taxes and fees
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
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

Maui Beach Hotel

Maui Beach Hotel

10/10 Excellent
"Great spot to recover from the long flight. Food at nearby restaurant was very good."
Lillian 1-night trip
Posted 5 hours ago
Maui Beach Hotel

Find out more about Upcountry Maui

Everything you need to know about Upcountry Maui vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upcountry Maui vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upcountry Maui in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $228 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui vacation 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 vacation.

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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