Upcountry Maui Holiday Homes from €271: Search Top House Rentals

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Our top choices for Upcountry Maui holiday homes

A swimming pool with a wooden deck, surrounded by palm trees and tropical plants.

1. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Makawao

Lisa B.

includes taxes & fees

17 Nov - 18 Nov

A residential street lined with palm trees and houses.

2. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku

Will W.

includes taxes & fees

15 Nov - 16 Nov

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

3. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku

Amy C.

includes taxes & fees

30 Nov - 1 Dec

A house with a well-maintained lawn, a wooden deck, and a staircase leading to a balcony.

4. Yonegan Maui Getaways - Haiku

Haiku

Nancy

includes taxes & fees

17 Nov - 18 Nov

A beach with red sand, waves, and a rocky outcrop in the distance.

5. Fisher's Hana Bay Hale, Across from Hana Bay

Hana Town Center

Val S.

includes taxes & fees

18 Nov - 19 Nov

A beach with palm trees and a clear sky.

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

North Kihei

" Kīhei Casita House Stay (above the Main House): just lovely - would stay there again - reasonably priced - fully functioning everything - and easy outside access - we actually stayed in the Main House for one week and then one week in the Casita - while in the Main House the Casita was occupied and no noise issues at all. Fairly easy access to beaches and beach shopping. Excellent communication with host."

Michael C.

includes taxes & fees

16 Nov - 17 Nov

A beach with red sand, scattered rocks, and a distant rocky island.

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

Hana Town Center

Jennifer

includes taxes & fees

21 Nov - 22 Nov

A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

8. Hale Nihi - Paia, Maui

Paia

Chameil H.

includes taxes & fees

25 Nov - 26 Nov

A bed with a patterned bedspread, two pillows with text, a green pillow with 'beach is my happy place' text, and a wooden headboard.

9. HALE NIHI, Paia, Maui

Paia

Peter M.

includes taxes & fees

13 Dec - 14 Dec

A beach with a wooden walkway, palm trees, and a clear blue sky.

10. Kamaole Sands 3104-Bright and Fresh!

South Kihei

Koree L.

includes taxes & fees

6 Dec - 7 Dec

A lush bamboo forest with a pathway leading to a building.

11. Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Kaʻeleku

Mary B.

includes taxes & fees

17 Nov - 18 Nov

A beach with a silhouette of a tree and a distant island during sunset.

12. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Kaʻeleku

Nancy

includes taxes & fees

14 Nov - 15 Nov

A beach with dark volcanic rocks in the foreground and a forested cliff in the background.

13. Beautiful Home in paradise!

Kaʻeleku

Monafou M.

includes taxes & fees

14 Nov - 15 Nov

A house with a covered porch, a staircase leading to the entrance, and a well-maintained garden.

14. The Pikake Suite at The Historic Wailuku Inn

Wailuku

Quinten M.

includes taxes & fees

14 Nov - 15 Nov

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

15. Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

South Kihei

Elizabeth M.

includes taxes & fees

18 Nov - 19 Nov

A modern house entrance with a stone wall, a wooden bench, and potted plants.

16. Featured on Staycation TV Stunning Modern Home Surrounded by Nature

Haiku-Pauwela

Greg B.

includes taxes & fees

11 Dec - 12 Dec

A swimming pool surrounded by lush tropical vegetation and lounge chairs.

17. Private Hot Tub + Pool Access + AC - Star Lookout

Haiku

Bob E.

includes taxes & fees

14 Nov - 15 Nov

An outdoor lounge area with wooden furniture and green cushions, a pool, and a view of the surrounding greenery.

18. Villa 8

South Kihei

Taylor M.

includes taxes & fees

1 Dec - 2 Dec

A living room with a sofa, bench, and a view of a garden through a glass door.

19. Tropical Vacation Rental Near Hana Bay & Waianapanapa State Park, Hawaii

Hana Town Center

includes taxes & fees

16 Nov - 17 Nov

A wooden fence with a sign reading "WOODSTOCK" and a peace sign.

20. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

North Kihei

Kristin P.

includes taxes & fees

16 Nov - 17 Nov

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Top Upcountry Maui Hotel Reviews

Maui Seaside Hotel

8/10 Good

"We were unable to charge our mobile devices. The room did not have any usb outlets. Fortunately we could charge our devices in our rented auto."

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent

"I loved the spacious rooms at the Hokupa a. The staff was very friendly and helpful. I like the concept of the lanai, however there are a few things that could be improved. The ceiling over the bedding and pool area is piped. Birds enjoy hanging out there and pooping right on the bed. It is difficult to relax where pigeons are hanging over your head going to the bathroom, My recommendation is to place a nice netting on the ceiling to cover the pipe. It will prevent the birds from hanging there. Additionally at the Hale restaurant and the lanai, birds are flying all over. A few jumped up on the tables in the lanai where the food was being served. This is very unsanitary. In the restaurant a woman screamed when a pigeon jumped onto her plate. I have been to many open restaurants and I do enjoy them, however something needs to be done to reduce the birds. Valerie, Leroy, Chris, Jenoveeve and the woman at the front desk were very friendly. The young ladies who worked the Lanai front desk were awesome and the bartenders were amazing and a lot of fun. Also a shout out to the young lady in charge of Karaoke, she made the party a lot of fun. Recommendation: Clean the lanai heated pool, the Adult heated pool and the adult pool. I own a pool and take pride in keeping it sanitary. I didnt see anyone during my stay skim or clean these pools. I noticed quite a bit of degree in each, Last comment but an important one, housekeeping is great and the hospitality room is greatly appreciated."

Aston Mahana at Kaanapali

10/10 Excellent

"This is my first time going to Hawaii. This hotel is somewhat difficult to find but it is the best hotel I ever stayed. My room was very cozy with perfect ocean view. I felt like enough to just stay in the room for the whole vacation because it was so nice. Thanks to the staff they very helpful and friendly. Number one recommendation!"

Fairmont Kea Lani Maui

8/10 Good

"Our first night we were notified that there would be an electricity outage for a couple of hours but had no idea or expectation we would be having direct service over our room. The noise woke both of us and kept us up for the entire two hours. The next day we were able to change our room but certainly did not expect to start our first night in paradise without any sleep !!"

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews	2,252
Accommodation	189 Holiday Homes
Lowest Price	€271
Highest Price	€2,816

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Check prices for these dates

Our top choices for Upcountry Maui holiday homes

1. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

2. Haiku Hale - 3 Bedroom Maui Getaway!

3. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

4. Yonegan Maui Getaways - Haiku

5. Fisher's Hana Bay Hale, Across from Hana Bay

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

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

8. Hale Nihi - Paia, Maui

9. HALE NIHI, Paia, Maui

10. Kamaole Sands 3104-Bright and Fresh!

11. Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

12. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

13. Beautiful Home in paradise!

14. The Pikake Suite at The Historic Wailuku Inn

15. Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

16. Featured on Staycation TV Stunning Modern Home Surrounded by Nature

17. Private Hot Tub + Pool Access + AC - Star Lookout

18. Villa 8

19. Tropical Vacation Rental Near Hana Bay & Waianapanapa State Park, Hawaii

20. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Find holiday rentals that suit your style

Top Upcountry Maui Hotel Reviews

Maui Seaside Hotel

The Westin Maui Resort & Spa, Ka'anapali

OUTRIGGER Kaanapali Beach Resort

Maui Coast Hotel

Sheraton Maui Resort & Spa

Aston Maui Kaanapali Villas

Aston Mahana at Kaanapali

Hilton Vacation Club Ka'anapali Beach Maui

Fairmont Kea Lani Maui

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Upcountry Maui

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upcountry Maui holiday homes

1. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

2. Haiku Hale - 3 Bedroom Maui Getaway!

3. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

4. Yonegan Maui Getaways - Haiku

5. Fisher's Hana Bay Hale, Across from Hana Bay

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

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

8. Hale Nihi - Paia, Maui

9. HALE NIHI, Paia, Maui

10. Kamaole Sands 3104-Bright and Fresh!

11. Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

12. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

13. Beautiful Home in paradise!

14. The Pikake Suite at The Historic Wailuku Inn

15. Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

16. Featured on Staycation TV Stunning Modern Home Surrounded by Nature

17. Private Hot Tub + Pool Access + AC - Star Lookout

18. Villa 8

19. Tropical Vacation Rental Near Hana Bay & Waianapanapa State Park, Hawaii

20. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Find holiday rentals that suit your style

Top Upcountry Maui Hotel Reviews

Maui Seaside Hotel

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Explore a world of travel with Expedia