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Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

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.
The price is AU$1,169
includes taxes & fees
7 Oct - 8 Oct
Haiku Hale - 3 Bedroom Maui Getaway!

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
The price is AU$557
includes taxes & fees
29 Sept - 30 Sept
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

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.
The price is AU$590
includes taxes & fees
29 Sept - 30 Sept
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

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
The price is AU$563
includes taxes & fees
29 Sept - 30 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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.
The price is AU$707
includes taxes & fees
30 Sept - 1 Oct
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

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.
The price is AU$731
includes taxes & fees
13 Oct - 14 Oct
Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access

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
The price is AU$443
includes taxes & fees
29 Sept - 30 Sept
Yonegan Maui Getaways - Haiku - Unit 6

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.
The price is AU$800
includes taxes & fees
30 Sept - 1 Oct
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

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
The price is AU$487
includes taxes & fees
3 Oct - 4 Oct
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

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.
The price is AU$585
includes taxes & fees
27 Sept - 28 Sept
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

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
The price is AU$563
includes taxes & fees
29 Sept - 30 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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.
The price is AU$527
includes taxes & fees
7 Oct - 8 Oct
Romantic 1 BR Condo with King Tempurpedic

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.
The price is AU$565
includes taxes & fees
28 Sept - 29 Sept
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

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.
The price is AU$662
includes taxes & fees
3 Oct - 4 Oct
Hale Nihi - Paia, Maui

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.
The price is AU$578
includes taxes & fees
3 Oct - 4 Oct
1 B/R Sleeps 4 Condo across from Kamaole II Beach - KKN252 - HOTEL Zone

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.
The price is AU$785
includes taxes & fees
27 Sept - 28 Sept
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

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.
The price is AU$523
includes taxes & fees
27 Sept - 28 Sept
Across from Kamaole 2 Beach, concrete building, well maintained.

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
The price is AU$488
includes taxes & fees
26 Oct - 27 Oct
Aston Maui Hill

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)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$603
includes taxes & fees
27 Sept - 28 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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.
The price is AU$588
includes taxes & fees
9 Oct - 10 Oct
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

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, 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 favourite 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 depend 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 AU$298 per night. Entering your travel dates in the search wizard might find you 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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