A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Upcountry Maui vacation rentals

A residential street lined with palm trees and houses.

1. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (8 reviews)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
United States
Linda S.
$668 nightly
The price is $787
Sep 27 - Sep 28
Total with taxes and fees
Haiku Hale - 3 Bedroom Maui Getaway!
A paved pathway leading to a gate with red pillars, surrounded by lush greenery and palm trees, with a view of the ocean in the background.

2. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (531 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
$315 nightly
The price is $371
Sep 29 - Sep 30
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A living room with a sofa, coffee table, and a large mirror. There is a sliding glass door leading to an outdoor area with a table and chairs.

3. Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (47 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
$336 nightly
The price is $396
Sep 29 - Sep 30
Total with taxes and fees
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
A balcony with a table set for two, featuring a bottle of wine and two glasses.

4. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (308 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
$322 nightly
The price is $378
Sep 27 - Sep 28
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
An aerial view of a coastal area with a clear pathway leading to a beach, surrounded by lush greenery and rocky coastline.

5. Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (110 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
$403 nightly
The price is $474
Sep 30 - Oct 1
Total with taxes and fees
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
A coastal resort with beachfront properties, a clear view of the ocean, and a mountainous backdrop.

6. Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access

Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access
South Kihei
9.6 out of 10, Exceptional, (135 reviews)
"Location; proximity to beach and stores/restaurants"
United States
Sharon O.
$420 nightly
The price is $495
Oct 13 - Oct 14
Total with taxes and fees
Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

7. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (42 reviews)
"Everything was great."
United States
Bryan
$293 nightly
The price is $294
Sep 29 - Sep 30
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 6
A pathway leading to a beach with dense green foliage on either side.

8. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
South Kihei
9.8 out of 10, Exceptional, (97 reviews)
"Kitchen was fully equipped. Condo was very clean and host was promt with replys. Loved our stay "
Canada
Lori D.
$451 nightly
The price is $531
Sep 27 - Sep 28
Total with taxes and fees
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A beach with clear blue water, a sandy shore, and a distant mountain.

9. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.6 out of 10, Exceptional, (87 reviews)
"We loved our stay! Great location"
United States
Madison
$278 nightly
The price is $327
Oct 2 - Oct 3
Total with taxes and fees
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

10. Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
South Kihei
9.2 out of 10, Wonderful, (91 reviews)
"Location was perfect. We were there right after all of the flooding and the road was damaged but did not affect our stay at all. Our host was always responsive and made sure we were comfortable! Would surely stay again.:)"
United States
Melissa P.
$339 nightly
The price is $399
Sep 27 - Sep 28
Total with taxes and fees
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
A table with a bottle and glasses on a red mat, surrounded by red chairs on a balcony with a view of palm trees and a tennis court.

11. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (280 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
$322 nightly
The price is $378
Sep 27 - Sep 28
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

12. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (63 reviews)
"The condo property was beautiful and in a great location. We had to book last minute due to storms affecting our initial booking and host was very responsive. "
United States
Kathryn R.
$303 nightly
The price is $356
Oct 4 - Oct 5
Total with taxes and fees
Romantic 1 BR Condo with King Tempurpedic
A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

13. 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (317 reviews)
"Kevin was a great host! Communication was prompt and he gave wonderful suggestions on places to eat, things to do.The condo was beautiful, very cozy and clean.We would definitely stay here again"
United States
Janet M.
$323 nightly
The price is $381
Sep 28 - Sep 29
Total with taxes and fees
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

14. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
$377 nightly
The price is $444
Sep 27 - Sep 28
Total with taxes and fees
Hale Nihi - Paia, Maui
A sandy beach with footprints, a few people, and a boat.

15. 1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
South Kihei
9.4 out of 10, Exceptional, (61 reviews)
"great place for walking to the beach"
United States
Kim & Tom C.
$329 nightly
The price is $388
Oct 1 - Oct 2
Total with taxes and fees
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone
A beach with palm trees and a clear sky.

16. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
Wailea
10.0 out of 10, Exceptional, (164 reviews)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
$446 nightly
The price is $525
Sep 27 - Sep 28
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A beach with people swimming and sunbathing, palm trees, and a building in the background.

17. Across from Kamaole 2 Beach, concrete building, well maintained.

Across from Kamaole 2 Beach, concrete building, well maintained.
South Kihei
10.0 out of 10, Exceptional, (167 reviews)
"Great location!"
United States
Tyler B.
$300 nightly
The price is $353
Sep 27 - Sep 28
Total with taxes and fees
Across from Kamaole 2 Beach, concrete building, well maintained.
A resort with a swimming pool, palm trees, and ocean views.

18. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (977 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
$298 nightly
The price is $353
Oct 26 - Oct 27
Total with taxes and fees
Aston Maui Hill
A beach with red sand, scattered rocks, and a distant rocky island.

19. Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (467 reviews)
"When can we go back? What an amazing place to stay in and a great house/host."
United States
Jeffrey F.
$346 nightly
The price is $408
Sep 27 - Sep 28
Total with taxes and fees
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
A beach with clear blue water, rocky shore, and palm trees.

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

Condo w/ Lanai at Beginning of Road to Hana!
Paia
9.2 out of 10, Wonderful, (45 reviews)
"This was the perfect stay to start the Road to Hana and the town of Paia is so lovely and had a lot of food options. The beaches around this area were some of our favorite. If you can, make a reservation at Mamas Fishhouse or try and walk in around lunch time-it’s worth every penny! "
United States
Kiana C.
$338 nightly
The price is $398
Oct 5 - Oct 6
Total with taxes and fees
Condo w/ Lanai at Beginning of Road to Hana!
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 Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"All people are nice and helpful!"
Ameneh 4-night trip
Posted less than an hour ago
Maui Seaside 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 $213 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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