Holiday Homes in Upcountry Maui

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Upcountry Maui holiday homes

Property grounds
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (72)
"We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! "
United States
Kari L.
The price is AU$4,457
includes taxes & fees
6 Jan - 7 Jan 2026
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Fridge, microwave, oven, stovetop
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!

PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!

PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
Makawao
10.0 out of 10, Exceptional, (50)
"Eve and her family were incredibly kind and welcoming. The property was better than we hoped with ample space for the kids to explore. We loved our stay and would come back!"
United States
Jessica S.
The price is AU$3,945
includes taxes & fees
27 Dec - 28 Dec
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
Property grounds
Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (4)
"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$1,852
includes taxes & fees
4 Jan - 5 Jan 2026
Haiku Hale - 3 Bedroom Maui Getaway!
Beach towels
Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (409)
"Great location for a Hana to Ka'anapali trip. "
United States
Anonymous traveller
The price is AU$599
includes taxes & fees
20 Jan - 21 Jan 2026
Fisher's Hana Bay Hale, Across from Hana Bay
Beach towels
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

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (414)
"Great stay. "
United States
Anthony A.
The price is AU$529
includes taxes & fees
24 Jan - 25 Jan 2026
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Garden
Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (12)
"Loved having the hot tub to come home to!!"
United States
Pedro
The price is AU$418
includes taxes & fees
5 Jan - 6 Jan 2026
Yonegan Maui Getaways - Haiku
Property grounds
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Kaʻeleku
9.8 out of 10, Exceptional, (77)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
The price is AU$1,524
includes taxes & fees
12 Jan - 13 Jan 2026
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Sun-loungers, beach towels
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.4 out of 10, Exceptional, (147)
"Great space. Centrally located with easy proximity to food & groceries. Perfect for our needs. Comfy bed too. "
United States
Tracy A.
The price is AU$949
includes taxes & fees
8 Jan - 9 Jan 2026
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Outdoor dining
Hinano Suite | Historic Maui Hideaway

Hinano Suite | Historic Maui Hideaway

Hinano Suite | Historic Maui Hideaway
Wailuku
10.0 out of 10, Exceptional, (3)
"Thank you for a wonderful stay. Our suite was great and comfortable. We well truly be back."
United States
JoAnn H.
The price is AU$746
includes taxes & fees
4 Jan - 5 Jan 2026
Hinano Suite | Historic Maui Hideaway
Sun-loungers, beach towels
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

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (109)
"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$812
includes taxes & fees
28 Dec - 29 Dec
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Outdoor dining
Experience luxury at The Ulu Suite | Garden patio

Experience luxury at The Ulu Suite | Garden patio

Experience luxury at The Ulu Suite | Garden patio
Wailuku
10.0 out of 10, Exceptional, (4)
"Parking and check in was easy and just as described. The interior was simple, yet felt upscale. Lovely original art on the walls, comforts bed, and bathroom and shower were wonderful. Would stay here again. "
United States
e o.
The price is AU$753
includes taxes & fees
7 Jan - 8 Jan 2026
Experience luxury at The Ulu Suite | Garden patio
Fridge, microwave, oven, stovetop
Hana Homestead by the Beach

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (138)
"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "
United States
Christopher
The price is AU$2,114
includes taxes & fees
21 Jan - 22 Jan 2026
Hana Homestead by the Beach
Pool
New! The Aloha Cottage in Puamana, Maui Hawaii

New! The Aloha Cottage in Puamana, Maui Hawaii

New! The Aloha Cottage in Puamana, Maui Hawaii
Lahaina
9.8 out of 10, Exceptional, (86)
"Cottage was clean and well kept. Location is convenient to shopping, dining, and many beaches including a small beach just a short walk from the property. Stay was very enjoyable."
United States
Robert B.
The price is AU$1,523
includes taxes & fees
13 Jan - 14 Jan 2026
New! The Aloha Cottage in Puamana, Maui Hawaii
Pool
Oceanview Retreat in Puamana – Steps from the Beach & Surf

Oceanview Retreat in Puamana – Steps from the Beach & Surf

Oceanview Retreat in Puamana – Steps from the Beach & Surf
Lahaina
10.0 out of 10, Exceptional, (2)
"This property had everything you would want in a vacation home. Great location. We enjoyed the beach, community pool and grounds. The photos were exactly as pictured. We had a great time in your home. Thank you for hosting us."
United States
Joey M.
The price is AU$1,891
includes taxes & fees
5 Jan - 6 Jan 2026
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Property grounds
OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS

OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS

OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS
Lahaina
10.0 out of 10, Exceptional, (26)
"Fantastic location and great communication from Kevin! We thoroughly enjoyed our stay!!"
United States
Janelle G.
The price is AU$3,179
includes taxes & fees
29 Dec - 30 Dec
OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS
Outdoor pool
★ - Rainbow Lookout! Private Hot Tub + Pool Access + New Central Conditioning

★ - Rainbow Lookout! Private Hot Tub + Pool Access + New Central Conditioning

★ - Rainbow Lookout! Private Hot Tub + Pool Access + New Central Conditioning
Haiku
10.0 out of 10, Exceptional, (24)
"Amazing!!! Great location, amazing hosts, great hospitality! We absolutely loved our stay!!"
United States
Anonymous traveller
The price is AU$1,443
includes taxes & fees
28 Dec - 29 Dec
★ - Rainbow Lookout! Private Hot Tub + Pool Access + New Central Conditioning
Terrace/patio
Villas By The Cove, Penthouse I · Modern Oceanview Townhome Steps to the Beach!

Villas By The Cove, Penthouse I · Modern Oceanview Townhome Steps to the Beach!

Villas By The Cove, Penthouse I · Modern Oceanview Townhome Steps to the Beach!
South Kihei
10.0 out of 10, Exceptional, (18)
"This spot is amazing. You cant find a better spot on the island. "
United States
Jon L.
The price is AU$2,762
includes taxes & fees
7 Jan - 8 Jan 2026
Villas By The Cove, Penthouse I · Modern Oceanview Townhome Steps to the Beach!
2 bedrooms, desk, iron/ironing board, travel cot
NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!
Lahaina
10.0 out of 10, Exceptional, (27)
"This was a wonderful stay with awesome hosts! Great location and perfect for families"
United States
Carter F.
The price is AU$2,328
includes taxes & fees
31 Dec - 1 Jan 2026
NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!
Terrace/patio
Villas By The Cove, Plantation House · Dreamy Indoor-Outdoor Living Opposite a Sandy Beach

Villas By The Cove, Plantation House · Dreamy Indoor-Outdoor Living Opposite a Sandy Beach

Villas By The Cove, Plantation House · Dreamy Indoor-Outdoor Living Opposite a Sandy Beach
South Kihei
10.0 out of 10, Exceptional, (55)
"Well managed, clean, good location"
United States
Andrew P.
The price is AU$2,705
includes taxes & fees
4 Jan - 5 Jan 2026
Villas By The Cove, Plantation House · Dreamy Indoor-Outdoor Living Opposite a Sandy Beach
Fridge, microwave, oven, stovetop
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC
Lahaina
10.0 out of 10, Exceptional, (4)
"Wonderful experience. Loved the house... bathtub was excellent!"
United States
Marcy M.
The price is AU$2,490
includes taxes & fees
22 Jan - 23 Jan 2026
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upcountry Maui Hotel Reviews

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"The hotel was clean and in a great location. Hotel staff were all great. Rooms were spacious and clean."
Christian Jordan 5-night trip
Posted 2 days ago
Royal Lahaina Resort & Bungalows

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
1,455
Accommodation
186 Holiday Homes
Lowest Price
AU$418
Highest Price
AU$4,457

Explore a world of travel with Expedia