Upcountry Maui Holiday Rentals, Hawaii: Private House Rentals

A barren volcanic landscape with rugged terrain and distant mountains.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Upcountry Maui

Waterpark

Condo

Hot tub

Apartment

Pet friendly

Resort

Spa

Apart hotel

Family friendly

Pool

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

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 modern living room with a sofa set, a coffee table, and a wall-mounted TV.

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

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

1. Gods Peace Of Maui

Makawao

akiko

Rp2.977.353

Rp3.534.474 total

includes taxes & fees

6 Oct - 7 Oct

A swimming pool with lounge chairs and a hedge.

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

A wooden structure with a balcony overlooking a garden with palm trees and red flowers.

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

2. Lumeria Maui Educational Retreat Center

Makawao

Dean

Rp6.283.251

Rp8.944.938 total

includes taxes & fees

3 Nov - 4 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

Rp10.246.386

Rp22.265.415 total

includes taxes & fees

31 Oct - 1 Nov

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

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.

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

4. Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Mary Ann

Rp13.558.132

Rp17.255.313 total

includes taxes & fees

25 Oct - 26 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 multi-story hotel with a central courtyard, balconies, and a view of the ocean.

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.

5. Residence Inn by Marriott Maui Wailea

Wailea

Keala

Rp8.189.956

Rp9.722.460 total

includes taxes & fees

22 Oct - 23 Oct

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

A balcony with a view of the ocean and sunset.

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.

6. Fairmont Kea Lani Maui

Wailea

Blanca Veronica

Rp18.937.038

Rp23.732.991 total

includes taxes & fees

24 Oct - 25 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.

7. Wailea Beach Resort - Marriott, Maui

Wailea

Christina

Rp10.496.734

Rp13.713.348 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern hotel with a large entrance, palm trees, and a sign indicating it is the Maui Coast Hotel.

A beach with palm trees, umbrellas, and people.

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

8. Maui Coast Hotel

South Kihei

Rachel

Rp3.395.792

Rp4.858.897 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A resort with a pool, beach, and mountain view.

9. Four Seasons Resort Maui at Wailea

Wailea

Quinn

Rp18.329.050

Rp22.926.297 total

includes taxes & fees

19 Oct - 20 Oct

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

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

A hotel with a sign for Days Inn by Wyndham, surrounded by palm trees and a well-maintained lawn.

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

10. Days Inn by Wyndham Maui Oceanfront

South Kihei

Mary

Rp3.690.845

Rp4.381.475 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

A spacious lounge area with a modern design, featuring a large sofa, a coffee table, and a seating area with thatched umbrellas.

11. AC Hotel by Marriott Maui Wailea

Wailea

Janice

Rp8.029.018

Rp10.062.145 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

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

Wailea

Ma Gabriella

Rp13.161.152

Rp16.678.547 total

includes taxes & fees

5 Nov - 6 Nov

A poolside area with a fire pit, lounge chairs, and umbrellas.

A bar area with a view of palm trees and the ocean at sunset.

A resort with a pool, a covered outdoor area, and a stone wall.

A spacious indoor area with a high ceiling, large windows, and a view of the ocean.

13. Hotel Wailea Maui

Wailea

Rashonner

Rp15.181.818

Rp19.084.117 total

includes taxes & fees

31 Oct - 1 Nov

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

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

14. Hilton Grand Vacations Club Maui Bay Villas

North Kihei

Ana

Rp5.707.934

Rp7.408.847 total

includes taxes & fees

17 Oct - 18 Oct

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

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

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

15. Aston Maui Hill

South Kihei

Lisa

Rp5.485.303

Rp6.511.714 total

includes taxes & fees

3 Nov - 4 Nov

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

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.

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

16. Ho‘olei Villas at Grand Wailea

Wailea

Justin Robert

Rp30.807.467

Rp37.732.345 total

includes taxes & fees

17 Oct - 18 Oct

A hotel lobby with a large arched window overlooking a beach, several wooden chairs, and ambient lighting.

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

17. Fairmont Kea Lani Maui Villa Experience

Wailea

Sze Wai

Rp47.190.598

Rp57.273.364 total

includes taxes & fees

28 Oct - 29 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.

18. Mana Kai Maui- Official Onsite Rental

South Kihei

Baijumon

Rp10.782.846

Rp14.245.951 total

includes taxes & fees

6 Oct - 7 Oct

A beach with clear turquoise water, a sandy shore, and a backdrop of a resort area with buildings and trees.

A balcony with a view of a landscaped area, palm trees, and a building with multiple floors.

A modern hotel with a central pathway, surrounded by lush greenery and palm trees.

A resort with a pool, lush greenery, and a view of the ocean.

19. Aston at the Maui Banyan

South Kihei

Perla

Rp3.071.233

Rp4.176.661 total

includes taxes & fees

4 Nov - 5 Nov

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

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

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

20. Maui Seaside Hotel

Kahului

Anthony

Rp3.335.422

Rp4.490.286 total

includes taxes & fees

26 Oct - 27 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"Clean room, friendly staff. Pool area was small but relaxing. Our partial ocean view was great. Wish power had not been out during our stay, it was due to high winds."

Maui Seaside Hotel

10/10 Excellent

"Super friendly staff. Old facility but rooms had a lot of extras and were spotless. Booked via Travelocity, 1/2 the price."

Napili Shores Maui by OUTRIGGER

10/10 Excellent

"FABULOUS! Clean, roomy, best bed"

Aston Maui Kaanapali Villas

8/10 Good

"Great place will stay again!"

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent

"Beautiful grounds, the M floor had great snacks all day and the staff was great. My favorite place to stay in Ka’anapali."

Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"If you’re thinking of going to Maui for your honeymoon- think the Wailea Beach Resort by Marriott. You’ll be happy you did. Truly an amazing resort with unbeatable sunset and ocean views. Shay at the Adult Pool is absolutely amazing!!"

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!"

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent

"We had a wonderful visit"

Andaz Maui at Wailea Resort - a concept by Hyatt

10/10 Excellent

"We really enjoyed our stay. We booked 2 weeks but ended up leaving a couple days early because of the potential hurricane threat. Staff was amazing!! Everyone was so very friendly! Loved the walking path to other hotels, shops, restaurants! Rooms were nice, loved the coffee, chips, cookies, cute reusable bag provided. Wished it had another mirror somewhere to get ready while another was showering and wished there was more space for clothes. Though again we were there for 2 weeks so had a lot. They had full sized shampoo, conditioner, body wash, ironing board and cloths steamer, nice hair dryer and robes. Small reusable water bottles with ice and water available on each floor. Food by the pool was good. We rented a car for part of our stay, so super close to Kīhei for food, other beaches, shops but $60/day to park and had to use valet. Pools were beautiful! Reef safe sunscreen 30 & 50 were provided at every pool. We were a little disappointed that 2 pools were being worked on and we didn’t know it beforehand. Very noisy at one pool M-F for hours. And limited shady spots, and if windy, shade umbrellas had to come down. You could purchase cabanas in the shade for an extra $250 I believe but many sat empty at all pools. Beach was rough after the storm (can’t be helped because of weather) but no one was working on steps, path to get down to the beach. Other hotels were on it days after it happened… just something to be prepared, aware of. We were able to snorkel."

More cheap stays in Upcountry Maui

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI

Rp2.977.353

Rp3.534.474 total

6 Oct - 7 Oct

includes taxes & fees

Days Inn by Wyndham Maui Oceanfront

2980 S Kihei Road Kihei HI

Rp3.690.845

Rp4.381.475 total

27 Oct - 28 Oct

includes taxes & fees

Grand Champions

155 Wailea Ike Pl Kihei HI

Rp753.985

Rp9.040.956 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

8.6/10 Excellent! (126 reviews)

Petite Retreat at Kahana Falls

4260 Lower Honoapiilani Rd Lahaina HI

Get rates

7.8/10 Good! (17 reviews)

Explore a world of travel with Expedia

More ways to book

Book Hotels in Upcountry Maui on Expedia.com

Find hotels in Upcountry Maui, HI from Rp3.534.474

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. Grand Wailea Maui, A Waldorf Astoria Resort

5. Residence Inn by Marriott Maui Wailea

6. Fairmont Kea Lani Maui

7. Wailea Beach Resort - Marriott, Maui

8. Maui Coast Hotel

9. Four Seasons Resort Maui at Wailea

10. Days Inn by Wyndham Maui Oceanfront

11. AC Hotel by Marriott Maui Wailea

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

13. Hotel Wailea Maui

14. Hilton Grand Vacations Club Maui Bay Villas

15. Aston Maui Hill

16. Ho‘olei Villas at Grand Wailea

17. Fairmont Kea Lani Maui Villa Experience

18. Mana Kai Maui- Official Onsite Rental

19. Aston at the Maui Banyan

20. Maui Seaside Hotel

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

OUTRIGGER Kaanapali Beach Resort

Maui Seaside Hotel

Napili Shores Maui by OUTRIGGER

Aston Maui Kaanapali Villas

The Westin Maui Resort & Spa, Ka'anapali

Wailea Beach Resort - Marriott, Maui

Four Seasons Resort Maui at Wailea

Grand Wailea Maui, A Waldorf Astoria Resort

Andaz Maui at Wailea Resort - a concept by Hyatt

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

Go further with the Expedia app