Upcountry Maui Vacation Rentals from $193: Search Short-Term Rentals

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Our top choices for Upcountry Maui vacation rentals

A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

1. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku

$1,049 nightly

Oct 31 - Nov 1

Total with taxes and fees

A resort with a swimming pool, palm trees, and ocean views.

2. Aston Maui Hill

South Kihei

Michael

$300 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

3. Yonegan Maui Getaways - Haiku

Haiku

Matt

$283 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with a large island, a dining area with a view, and a living room with a sofa and chairs.

4. Kihei Ali'i Kai Condos with Free Parking

South Kihei

Angeline

$425 nightly

Oct 11 - Oct 12

Total with taxes and fees

A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

5. Signature Residences at Maui Banyan

South Kihei

Mai

$482 nightly

Oct 11 - Oct 12

Total with taxes and fees

A beach with clear turquoise water, a sandy shore, and a distant mountain.

6. Wonderful South Maui Beach Condos

South Kihei

John

$437 nightly

Nov 1 - Nov 2

Total with taxes and fees

A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

7. Grand Champions by KBM

Wailea

Sean

$945 nightly

Oct 11 - Oct 12

Total with taxes and fees

A dining area with a table set for breakfast, including bread, fruit, and orange juice.

8. The Ocean View Residence

South Kihei

John

$575 nightly

Oct 12 - Oct 13

Total with taxes and fees

9. South Maui Beach Suites

South Kihei

$406 nightly

Nov 1 - Nov 2

Total with taxes and fees

A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

10. The Residences at Kamaole Sands Resort

South Kihei

George Lucas

$519 nightly

Oct 13 - Oct 14

Total with taxes and fees

A beach with clear blue water, a sandy shore, and palm trees.

11. The Kalama Residence

South Kihei

Rosalba

$707 nightly

Oct 11 - Oct 12

Total with taxes and fees

A beach with clear blue water, rocky shore, and palm trees.

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

Paia

$353 nightly

Oct 18 - Oct 19

Total with taxes and fees

A beach with palm trees, rocks, and the ocean.

13. Awesome Maui Vista Beach Suite

South Kihei

Laura

$437 nightly

Nov 1 - Nov 2

Total with taxes and fees

A tropical beach scene with palm trees, a clear blue sky, and a view of the ocean.

14. Waiohuli Beach Hale Ocean View Condos with Parking

Central Kihei

Phillip J

$460 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

Kannapali Beach Area

Joseph

$292 nightly

Nov 6 - Nov 7

Total with taxes and fees

A tropical garden with a waterfall, lush greenery, and a gazebo.

16. Aston Kaanapali Shores

Lahaina

Roopa Rani

$256 nightly

Oct 28 - Oct 29

Total with taxes and fees

A resort pool area with a hot tub, lounge chairs, and palm trees.

17. Villa, Garden View, 2-bedroom

Wailea

$1,401 nightly

Oct 12 - Oct 13

Total with taxes and fees

A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

18. Napili Shores Maui by OUTRIGGER

Lahaina

Shawn

$224 nightly

Oct 25 - Oct 26

Total with taxes and fees

A resort with multiple bungalow-style buildings, a swimming pool, and a beach.

19. Royal Lahaina Bungalows & Spa

Lahaina

AURA MARINA

$431 nightly

Nov 7 - Nov 8

Total with taxes and fees

A beach with clear blue water, palm trees, and a resort in the background.

20. Napili Village Hotel

Lahaina

Thomas

$163 nightly

Nov 3 - Nov 4

Total with taxes and fees

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Top Upcountry Maui Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent

"Great location beach and pool. Would stay again."

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"Good staff. Beware of pricing - a lot of hidden fees. Your total at expedia is not the actual total. Mandatory $45 dollar fee per day for I don't know what. $35 / day parking fee. Some other stuff. No chairs or umbrellas on the beach (another $90/day to rent those - separate vendor). Very good restaurant on premises. Our room had a good view (we upgraded), but as far as cleanliness it was mid. Smelled like someone smoked in it previously."

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent

"The swimming pools are very large. They have a kids pool that is like a foot and a half or two feet deep all around and barriers. To the other deeper pools. Has a slide for smaller kids ans a larger tube slide for 3 ft kids or taller. Good for adults too. Alot of pool space. Another more secluded pool by the beach. The rooms are great for my family of 5. All slept well and only had one neighbor since we stayed 9 night they were all great. We got the breakfast included. It was a made to order sandwich with egg and cheese and either ham sausage or bacon. But cant substitute also comes with juice. Was a good deal as it was for all my 5 members of the family. The beach was a bit washed out due to storms but overall we walked south from the more secluded beach to make sand castles and spend a day in the beach we liked it more than baby beach. There is also another beach just a couple more feet south where they have a whale exhibit and that beach has calms water usually but the storms knocked some rocks that stop the waves but still was better than baby beach in my opinion they have great beaches at the resort just a couple feet from there. And the sunsets are wow."

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 $193 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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Check prices for these dates

Our top choices for Upcountry Maui vacation rentals

1. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2. Aston Maui Hill

3. Yonegan Maui Getaways - Haiku

4. Kihei Ali'i Kai Condos with Free Parking

5. Signature Residences at Maui Banyan

6. Wonderful South Maui Beach Condos

7. Grand Champions by KBM

8. The Ocean View Residence

9. South Maui Beach Suites

10. The Residences at Kamaole Sands Resort

11. The Kalama Residence

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

13. Awesome Maui Vista Beach Suite

14. Waiohuli Beach Hale Ocean View Condos with Parking

15. Aston Maui Kaanapali Villas

16. Aston Kaanapali Shores

17. Villa, Garden View, 2-bedroom

18. Napili Shores Maui by OUTRIGGER

19. Royal Lahaina Bungalows & Spa

20. Napili Village Hotel

Find vacation rentals that suit your style

Top Upcountry Maui Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Find out more about Upcountry Maui

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