Holiday Homes in Upcountry Maui

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Upcountry Maui

Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is NZ$433
includes taxes & fees
17 Aug - 18 Aug
Yonegan Maui Getaways - Haiku
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Beach towels

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

9.6 out of 10, Exceptional, (388)
"The property was excellent, highly recommend. "
The price is NZ$596
includes taxes & fees
20 Aug - 21 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Fisher's Hana Bay Hale, Across from Hana Bay
Beach towels

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (394)
"Property was in a great location, very clean. We enjoyed our stay!"
The price is NZ$667
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Outdoor pool, a heated pool

Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach

9.8 out of 10, Exceptional, (153)
"Everything was great: the house, the location. Everything was perfect."
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Beautiful 3-bedroom townhome in Kihei
Property grounds

Beautiful 3-bedroom townhome in Kihei

9.6 out of 10, Exceptional, (4)
"We loved our stay! The place had everything the family needed for visiting the beach and the place was clean and comfortable. Would stay again! "
Beautiful 3-bedroom townhome in Kihei
Stunning views! Exclusive pool, spa and big private yard.
Exterior

Stunning views! Exclusive pool, spa and big private yard.

10.0 out of 10, Exceptional, (141)
"Lovely home with everything we would ever need. Wonderful hosts"
Stunning views! Exclusive pool, spa and big private yard.
87-2 is an elegant, remodeled 2-bedroom, 2.5-bath townhome with AC.
Beach nearby

87-2 is an elegant, remodeled 2-bedroom, 2.5-bath townhome with AC.

9.4 out of 10, Exceptional, (8)
"Booked for 11 days although no reviews were present. Pleasantly suprised at condition and location of the property versus the photos. Condo was clean and well stocked including beach chairs, beach equipment, and cooler in patio storage room. Development is a gated community that is very quiet and has usable beach and pool. Encountered only minor issues with the kitchen faucet and ice maker. Would book again."
87-2 is an elegant, remodeled 2-bedroom, 2.5-bath townhome with AC.
Remodeled, Ground floor studio at The Mahana #102
Outdoor pool

Remodeled, Ground floor studio at The Mahana #102

9.8 out of 10, Exceptional, (53)
"Clean, quiet, as advertised. "
Remodeled, Ground floor studio at The Mahana #102
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Outdoor dining

Mountain to Ocean Views Pole House @ Maui Adventure Villa

10.0 out of 10, Exceptional, (223)
"Great location with a great view. Very relaxing. "
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
On the beach, sun-loungers, beach towels

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

10.0 out of 10, Exceptional, (19)
"Excellent all around property"
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
Privacy In Paradise - Top Rated Vacation Home in West Maui
Pool

Privacy In Paradise - Top Rated Vacation Home in West Maui

10.0 out of 10, Exceptional, (139)
"It was simply amazing"
Privacy In Paradise - Top Rated Vacation Home in West Maui
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
On the beach, sun-loungers, beach towels

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

9.8 out of 10, Exceptional, (20)
"We loved our four days at this home. It was beautiful and so close to a lovely beach. Just wish we could have stayed longer!!"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Kaiholo Hale
Beach nearby

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (199)
"We stayed here 4 nights, perfect location for our activities. We did sunrise bike ride down Haleakala and Road to Hana. "
Kaiholo Hale
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Outdoor pool, a heated pool

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

10.0 out of 10, Exceptional, (86)
"Great location, clean, comfortable and well maintained. The owner was easy to work with and truly provided everything that you need for a great vacation."
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Exterior

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (227)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Stunning Beach Front Townhouse
Interior

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (94)
"Great location to spend a week to enjoy Maui "
Stunning Beach Front Townhouse
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Beach nearby, sun-loungers, beach towels

Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In

10.0 out of 10, Exceptional, (172)
"We had a great time. The house was very well organized and equipped "
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Puamana Ocean Front Tropical Paradise 226-1
Outdoor pool

Puamana Ocean Front Tropical Paradise 226-1

9.2 out of 10, Wonderful, (119)
"We loved our location and all the neighbors were very friendly"
Puamana Ocean Front Tropical Paradise 226-1
Brand New Kitchen & Updated Living Space - Oceanfront #216-2
On the beach

Brand New Kitchen & Updated Living Space - Oceanfront #216-2

9.2 out of 10, Wonderful, (37)
"Comfortable condo in a great location. Water & beach access through well maintained grounds right out the door. The whale & monk seal sighting really added to the incredible experience."
Brand New Kitchen & Updated Living Space - Oceanfront #216-2
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
Exterior

Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

10.0 out of 10, Exceptional, (72)
"Incredible property. Great location. Great managers. So kind. Maui is the best."
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
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.
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

Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

10/10 Excellent
"Beautiful property and wonderful staff. Pools and rooms were very nice. Only complaint is the bed was too soft. "
Kevin 6-night trip
Posted 1 day ago
Hyatt Regency Maui Resort & Spa