Upcountry Maui Holiday Rentals, Hawaii: Private House Rentals

A barren volcanic landscape with rugged terrain and distant mountains.

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Our top choices for Upcountry Maui hotels

A pathway leading to a house with a speed limit sign of 5, surrounded by palm trees and a grassy area.

A wooden house with a balcony, surrounded by lush greenery and palm trees.

A compact kitchen with a dining area, a refrigerator, a stove, and a window with curtains.

An outdoor patio area with a covered seating area, tables, and a barbecue grill.

1. Gods Peace Of Maui

Makawao

Guest highlights

Near Makawao Park
Shower and hot tub
Beautiful mountain and ocean view

฿5,602

฿6,650 total

includes taxes & fees

9 Oct - 10 Oct

A swimming pool with lounge chairs and a hedge.

A spacious lobby with a large chandelier, wooden paneling, and a central rug.

A house with a green roof, surrounded by lush tropical plants and trees.

A spacious room with a high ceiling, skylights, and a large window at the far end.

2. Lumeria Maui Educational Retreat Center

Makawao

Guest highlights

Lovely swimming pool for guests
Delicious breakfast options served
On-site spa with various treatments

฿11,246

฿16,146 total

includes taxes & fees

7 Nov - 8 Nov

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

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

A bedroom with a large bed, a ceiling fan, wooden flooring, and artwork on the walls.

A view from a balcony overlooking a landscaped garden with various plants and a distant view of houses.

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

Haiku

฿19,279

฿41,892 total

includes taxes & fees

31 Oct - 1 Nov

A poolside lounge area with outdoor seating, a fire feature, and umbrellas providing shade.

A modern living area with a wooden bar, seating, and a large TV.

A restaurant with outdoor seating overlooking a scenic view, featuring modern furniture and a glass-enclosed dining area.

An outdoor lounge area with a thatched roof, fire pit, and multiple seating arrangements.

4. AC Hotel by Marriott Maui Wailea

Wailea

Guest highlights

Beautiful and clean pool area
Quality food at the on-site restaurant
Breathtaking ocean view from room

฿14,271

฿17,939 total

includes taxes & fees

23 Oct - 24 Oct

A modern bar area with a long counter, multiple stools, and a large TV screen displaying a scenic view.

An outdoor seating area with wicker chairs and orange cushions, a fire feature, and a view of the hotel building in the background.

A resort pool area with sun loungers and umbrellas, surrounded by lush greenery and overlooking a body of water with a sunset in the background.

A multi-story hotel with a central courtyard, balconies, and a view of the ocean.

5. Residence Inn by Marriott Maui Wailea

Wailea

Guest highlights

Beautiful ocean view from rooms
Huge pool with hot tub
Free breakfast with gluten-free options

฿15,409

฿18,293 total

includes taxes & fees

22 Oct - 23 Oct

A pool with a waterfall feature, surrounded by palm trees and a stone structure.

A spacious balcony with a view of a pool and palm trees, furnished with wicker chairs and a coffee table.

An aerial view of a beach resort with rows of sun loungers, palm trees, and a view of the ocean.

A resort with a pond, a wooden bridge, and lush greenery.

6. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Guest highlights

Ocean view from the property
Large pool with bar
Beach chairs and umbrella available

฿25,510

฿32,466 total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a view of the ocean and palm trees.

A resort with a swimming pool, solar panels, and a view of the ocean.

A modern restaurant with a bar area, seating arrangements, and large windows providing views of the outdoors.

A beach with palm trees, umbrellas, and people.

7. Maui Coast Hotel

South Kihei

Guest highlights

Ocean view room with balcony
Large pool area with cabanas
Relaxing atmosphere on the balcony

฿6,389

฿9,142 total

includes taxes & fees

12 Oct - 13 Oct

A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

A bar area with a curved counter, multiple bar stools, and a view of palm trees and the ocean at dusk.

An aerial view of a resort with multiple pools, palm trees, and lounge areas.

A balcony with wicker furniture, a view of the ocean, palm trees, and a mountain in the distance.

8. Four Seasons Resort Maui at Wailea

Wailea

Guest highlights

Memorable views from the rooms
Fantastic adult pool service
Responsive and attentive staff

฿34,486

฿43,136 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a wooden bed, white bedding, a beach-themed picture on the wall, and a ceiling fan.

A living room with a sofa, ottoman, and chairs, a table with a lamp, and a view of the beach through a sliding glass door.

A balcony with a view of a beach, outdoor furniture, and a clear sky.

A beach with a sunset, palm trees, and a rocky shoreline.

9. Days Inn by Wyndham Maui Oceanfront

South Kihei

Guest highlights

Spectacular ocean view from rooms
Free parking in back lot
Clean and friendly staff service

฿6,944

฿8,244 total

includes taxes & fees

12 Oct - 13 Oct

A spacious balcony with wicker furniture, a view of the ocean, and a mountain in the distance.

A spacious lobby with a wooden ceiling, large windows, and a seating area with sofas and a coffee table.

A multi-story hotel with balconies, a well-maintained lawn, and palm trees.

A resort pool area with a waterfall, palm trees, and a building with balconies.

10. Hilton Grand Vacations Club Maui Bay Villas

North Kihei

Guest highlights

Beautiful pool area with lounge chairs
Clean kitchen for self-catering
Easy and secure parking available

฿10,739

฿13,940 total

includes taxes & fees

17 Oct - 18 Oct

A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.

A serene outdoor seating area with two tables covered in white tablecloths and wooden stools, overlooking a coastal view with the ocean and a distant island.

A well-maintained golf course with a clear view of the ocean and a winding path.

A deck with two lounge chairs facing a scenic ocean view, a wooden floor, and a modern architectural design.

11. Wailea Beach Resort - Marriott, Maui

Wailea

Guest highlights

Breathtaking ocean view from rooms
Large pool with fun features
Delicious food and dining on offer

฿19,750

฿25,802 total

includes taxes & fees

21 Oct - 22 Oct

A staircase with a view of a garden, palm trees, and a bridge.

A resort pool area with lounge chairs, umbrellas, and palm trees.

A resort with a large swimming pool, palm trees, and a view of the ocean.

A spacious lobby with a curved wooden arch, seating areas, and a bar.

12. Fairmont Kea Lani Maui

Wailea

Guest highlights

Beautiful ocean view from balcony
Great clean pools with chairs
Good food at on-site restaurants

฿33,948

฿42,657 total

includes taxes & fees

12 Oct - 13 Oct

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

A pool area with palm trees, a beach view, and a building with a sign reading "Five Palms Beach Grill".

A hotel with a modern architectural design, featuring a prominent building with multiple floors and a flat roof.

A lobby with a stone wall, a large blue mural of a turtle, and seating areas with a stone floor.

13. Mana Kai Maui- Official Onsite Rental

South Kihei

Guest highlights

Beautiful beach view from room
Nice warm pool access on-site
Professional staff on hand each day

฿20,288

฿26,804 total

includes taxes & fees

9 Oct - 10 Oct

A resort with multiple swimming pools, palm trees, and a view of the ocean.

A spacious lobby with a high ceiling, wooden columns, and a marble floor.

A bar with a wooden sign, multiple bar stools, and a patterned wall.

A circular fire pit with seating around it, outdoor umbrellas, and a view of the ocean at dusk.

14. Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

Guest highlights

Breathtaking ocean views from rooms
Very nice selection of pools
Lovely breakfast to start the day

฿26,781

฿33,777 total

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with lounge chairs and palm trees.

A modern bar area with a marble countertop, green upholstered chairs, and a unique light fixture.

An outdoor seating area with a circular fire pit surrounded by wicker furniture.

A Courtyard Marriott hotel with a covered entrance, multiple balconies, and lush landscaping.

15. Courtyard Maui Kahului Airport

Kahului

Guest highlights

Nice pool area with hot tub
Great food options from food trucks
Convenient airport shuttle service

฿12,082

฿14,343 total

includes taxes & fees

19 Oct - 20 Oct

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

A hotel with a pool, outdoor seating, and a view of the ocean.

A spacious living room with a sofa, a coffee table, and a television. There are large windows and a balcony visible.

An aerial view of a resort with multiple buildings, a swimming pool, and a view of the ocean.

16. Aston Maui Hill

South Kihei

Guest highlights

Beautiful swimming pool and hot tub
Spacious and beautiful room units
Easy free parking on-site

฿11,078

฿13,150 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a sofa, a coffee table, a chair, a lamp, and a window with curtains.

A hotel entrance with a sign reading 'MAUI SEASIDE HOTEL,' a wooden walkway, and a stone wall.

A pool area with lounge chairs and a view of a body of water and mountains.

17. Maui Seaside Hotel

Kahului

Guest highlights

Pool area with lounge chairs
Free Airport Shuttle service available

฿6,276

฿8,448 total

includes taxes & fees

26 Oct - 27 Oct

A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

A pool with a waterfall feature, lounge chairs, and palm trees under a sunset sky.

A spacious kitchen with a large island, wooden cabinets, and a view of the ocean.

A multi-level hotel atrium with a central bar, outdoor seating, and multiple balconies.

18. Ho‘olei Villas at Grand Wailea

Wailea

Guest highlights

Steps from Wailea Beach
Attentive service from restaurant staff

฿59,261

฿72,533 total

includes taxes & fees

22 Oct - 23 Oct

A terrace with wicker furniture, potted plants, and a view of the ocean.

A kitchen with a large window, a dining area with chairs, and a view of palm trees.

A spacious living area with a kitchen, dining area, and a balcony with a view of palm trees.

A spacious living area with a wooden staircase, a dining table, and a sofa.

19. Kohea Kai Hotel Maui

North Kihei

Guest highlights

Beautiful ocean view from room
Spacious pool and garden patio
Friendly and responsive front desk staff

฿4,350

฿6,162 total

includes taxes & fees

1 Nov - 2 Nov

A pool area with lounge chairs and umbrellas, surrounded by palm trees and overlooking the ocean.

A spacious living area with a wooden ceiling, large windows, and a view of the ocean.

A spacious room with a large sliding glass door leading to a lush garden with palm trees and a view of the ocean.

An aerial view of a coastal golf resort with multiple buildings, a well-maintained golf course, and a rocky shoreline.

20. Hana-Maui Resort, a Destination by Hyatt Residence

Hana Town Center

Guest highlights

Large pool with activities
Beautiful location near bungalows
Very good Huli Huli Chicken

฿15,578

฿20,270 total

includes taxes & fees

7 Nov - 8 Nov

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Stay near popular Upcountry Maui attractions

Haleakala Crater

9.6/10 (547 reviews)

One of the best places in the U.S. to watch the sunrise is this impressive centerpiece of Haleakalā National Park, marking the birthplace of the island of Maui.

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Maui Spa Retreat

6.6/10 (4 reviews)

Enjoy a trip to Maui Spa Retreat and popular activities such as surfing in Makawao. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

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Haleakalā Visitor Center

9.0/10 (2 reviews)

Explore the lovely green spaces of Haleakalā Visitor Center and enjoy the golf courses in Kula. Wander through the beautiful beaches and seaside in this relaxing area.

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Makawao Park

8.0/10 (2 reviews)

Explore the great outdoors at Makawao Park, a lovely green space in Makawao. Stroll along the area's seaside or simply savour its top-notch restaurants.

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Hoʻomana Spa Maui

You can take time to visit Hoʻomana Spa Maui during your travels to Makawao. Wander the beautiful beaches and seaside in the area.

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Kula Botanical Garden

Enjoy the beautiful sunsets and explore Kula Botanical Garden, a lovely green space in Kula. Stroll along the area's seaside or experience its great live music.

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Polipoli Spring State Recreation Area

Enjoy the beautiful sunsets and explore Polipoli Spring State Recreation Area, a lovely green space in Kula. Stroll along the beautiful beaches in this romantic area or visit its top-notch restaurants.

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Hosmer Grove

Explore the great outdoors at Hosmer Grove, a lovely green space in Kula. Stroll along the seaside in this relaxing area or seek out the yoga studios.

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Learn more about Upcountry Maui

Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing city also notable for its island views.

See all hotels in Upcountry Maui

Top Upcountry Maui Hotel Reviews

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent

"Great resort"

Aston Kaanapali Shores

10/10 Excellent

"My wife and I were there for the first time, and we really enjoyed everything."

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent

"Best resort pool in Maui"

Maui Beach Hotel

10/10 Excellent

"Very nice hotel"

Maui Coast Hotel

10/10 Excellent

"Greta place and cheap"

Hilton Vacation Club Ka'anapali Beach Maui

8/10 Good

"The pool is the best part of the hotel. The rooms are somewhat dated. Bar and food are very average but yet expensive."

Gods Peace Of Maui

10/10 Excellent

"Tammi and Mika were super sweet and helpful. The property was comfortable and they supplied some amenities to help with our stay. Beautiful property and the view, WOW! I will be looking them up again when I return. :)"

Aston Maui Kaanapali Villas

8/10 Good

"Great place will stay again!"

Four Seasons Resort Maui at Wailea

10/10 Excellent

"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"

More cheap stays in Upcountry Maui

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

฿5,602

฿6,650 total

9 Oct - 10 Oct

includes taxes & fees

Days Inn by Wyndham Maui Oceanfront

2980 S Kihei Road Kihei HI

฿6,944

฿8,244 total

12 Oct - 13 Oct

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

Grand Champions

155 Wailea Ike Pl Kihei HI

฿1,349

฿16,863 total

9 Oct - 10 Oct

includes taxes & fees

9.2/10 Wonderful! (9 reviews)

Maui Beach Vacation Club

515 S. Kihei Road Kihei HI

Get rates

AEI at Maui Banyan

2575 S Kihei Road Kihei HI

Get rates

Petite Retreat at Kahana Falls

4260 Lower Honoapiilani Rd Lahaina HI

Get rates

7.8/10 Good! (17 reviews)

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Book Hotels in Upcountry Maui on Expedia.com

Find hotels in Upcountry Maui, HI from ฿6,162

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Upcountry Maui

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Upcountry Maui hotels

1. Gods Peace Of Maui

2. Lumeria Maui Educational Retreat Center

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

4. AC Hotel by Marriott Maui Wailea

5. Residence Inn by Marriott Maui Wailea

6. Grand Wailea Maui, A Waldorf Astoria Resort

7. Maui Coast Hotel

8. Four Seasons Resort Maui at Wailea

9. Days Inn by Wyndham Maui Oceanfront

10. Hilton Grand Vacations Club Maui Bay Villas

11. Wailea Beach Resort - Marriott, Maui

12. Fairmont Kea Lani Maui

13. Mana Kai Maui- Official Onsite Rental

14. Andaz Maui at Wailea Resort - a concept by Hyatt

15. Courtyard Maui Kahului Airport

16. Aston Maui Hill

17. Maui Seaside Hotel

18. Ho‘olei Villas at Grand Wailea

19. Kohea Kai Hotel Maui

20. Hana-Maui Resort, a Destination by Hyatt Residence

Stay near popular Upcountry Maui attractions

Haleakala Crater

Maui Spa Retreat

Haleakalā Visitor Center

Makawao Park

Hoʻomana Spa Maui

Kula Botanical Garden

Polipoli Spring State Recreation Area

Hosmer Grove

Learn more about Upcountry Maui

Top Upcountry Maui Hotel Reviews

Hilton Grand Vacations Club Maui Bay Villas

Aston Kaanapali Shores

The Westin Maui Resort & Spa, Ka'anapali

Maui Beach Hotel

Maui Coast Hotel

Hilton Vacation Club Ka'anapali Beach Maui

Gods Peace Of Maui

Aston Maui Kaanapali Villas

Four Seasons Resort Maui at Wailea

More cheap stays in Upcountry Maui

Gods Peace Of Maui

Days Inn by Wyndham Maui Oceanfront

Grand Champions

Maui Beach Vacation Club

AEI at Maui Banyan

Petite Retreat at Kahana Falls

Explore a world of travel with Expedia

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