Holiday Homes in Upcountry Maui

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Featured Holiday Homes in Upcountry Maui and around

Our top choices for Upcountry Maui holiday homes

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 €197
includes taxes & fees
5 Oct - 6 Oct
Yonegan Maui Getaways - Haiku

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

9.6 out of 10, Exceptional, (398)
"The property was excellent, highly recommend. "
The price is €310
includes taxes & fees
8 Oct - 9 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (402)
"Wonderful property and a great place to stay in Hana"
The price is €348
includes taxes & fees
27 Sept - 28 Sept
Fisher's Hana Bay Hale, Across from Hana Bay

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

9.6 out of 10, Exceptional, (20)
"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

10.0 out of 10, Exceptional, (143)
"It was simply amazing"
Privacy In Paradise - Top Rated Vacation Home in West Maui

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (128)
"Plenty of room. Great kitchen for lots of cooks."
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

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

9.8 out of 10, Exceptional, (154)
"A great family destination. The grand kids spent hours in the pool. "
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach

The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!

9.8 out of 10, Exceptional, (100)
"This home is absolutely beautiful and accommodated our family of 25 well! It’s a block from the beach and has a great pool for kids of all ages! We loved our stay! "
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!

OCEANFRONT PUAMANA 136-1 - FUN IN THE SUN!

10.0 out of 10, Exceptional, (74)
"The location was stunning as well as the property itself. The owner was quick to respond to questions and was flexible with my schedule. Very clean and absolutely gorgeous! "
OCEANFRONT PUAMANA 136-1 - FUN IN THE SUN!

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

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

9.8 out of 10, Exceptional, (103)
"Beautiful property"
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views

Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2.0 star property
10.0 out of 10, Exceptional, (11)
"We had an amazing vacation with our kids and grandkids. We have already booked again for next year"
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

Kihei Maui Beach house - On the water

9.8 out of 10, Exceptional, (58)
"Mark was wonderful to work with. Some things could use some updates but overall it was a great location and we had a great stay."
Kihei Maui Beach house - On the water

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (200)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
Kaiholo Hale

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (78)
"Really enjoyed this home! "
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

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

9.8 out of 10, Exceptional, (23)
"Great location next to the beach! Kids loved the slide, pool, and bunkhouse. Beds were comfortable and the hosts were quick to respond for questions or issues. We had a great time! "
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

9.8 out of 10, Exceptional, (204)
"Perfect home for a large group. Beach is across the street the back to the pool when the waves got to be to much for our little ones. Great property manager! Great location! "
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

HALE NUI Luxury Retreat 5BD w Private Pool Hot Tub

10.0 out of 10, Exceptional, (84)
"The house was amazing and the location perfect! The view was unforgettable!! "
HALE NUI Luxury Retreat 5BD w Private Pool Hot Tub

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. "
Exceptional Upcountry Villa with breathtaking views
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.
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Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
2,272
Accommodation
183 Holiday Homes
Lowest Price
€197
Highest Price
€348