Holiday Homes in Upcountry Maui

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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Holiday Homes in Upcountry Maui

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Enjoy the serene ocean views and scenic beach with waves gently lapping at the shore.

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

9.6 out of 10, Exceptional, (385)
"The property was excellent, highly recommend. "
The price is NZ$593
includes taxes & fees
11 Aug - 12 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Remodeled, Ground floor studio at The Mahana #102
Relax by the pool with ocean views and lounge in style.

Remodeled, Ground floor studio at The Mahana #102

9.8 out of 10, Exceptional, (51)
"Clean, quiet, as advertised. "
Remodeled, Ground floor studio at The Mahana #102
Fisher's Hana Bay Hale, Across from Hana Bay
Enjoy a serene beach setting with a rocky outcrop in the distance, where waves gently lap against the shore.

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (389)
"Loved the location, there was even a peek-a-boo view of Hāna Bay. Lovely garden. "
The price is NZ$661
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
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! "
The price is NZ$767
includes taxes & fees
2 Aug - 3 Aug
Beautiful 3-bedroom townhome in Kihei
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Relax by the pool surrounded by lush tropical vegetation and enjoy a refreshing swim in the clear water.

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"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
Privacy In Paradise - Top Rated Vacation Home in West Maui
Enjoy a spacious outdoor living area with a well-maintained lawn, pool, and patio featuring outdoor furniture and a barbecue grill.

Privacy In Paradise - Top Rated Vacation Home in West Maui

10.0 out of 10, Exceptional, (137)
"The house is lovely with a great view to watch whales, sun, play and enjoy family time! "
Privacy In Paradise - Top Rated Vacation Home in West Maui
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Relax in this open-plan living area with expansive views of the surrounding landscape, featuring a hammock and comfortable seating.

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
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Exterior

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

9.8 out of 10, Exceptional, (139)
"This house is beautiful and we loved everything about our stay. It's in a great location to spend time exploring the Road to Hana. We can't wait to come back!"
The price is NZ$1,093
includes taxes & fees
31 July - 1 Aug
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Enjoy ocean views from the comfort of your room, with access to the beach and its sun loungers.

Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

9.4 out of 10, Exceptional, (58)
"Everything you need in the condo and enough beaches to try one every day!"
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Relax on the soft, sandy beach surrounded by lush greenery and palm trees.

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

10.0 out of 10, Exceptional, (18)
"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!
Location, Location.... Just Steps Away from the Ocean!
Guests can enjoy a refreshing swim in the pool overlooking the ocean and surrounding mountains.

Location, Location.... Just Steps Away from the Ocean!

9.6 out of 10, Exceptional, (142)
"Was a great property. Would stay again."
Location, Location.... Just Steps Away from the Ocean!
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Experience a serene beach setting with smooth sand and gentle waves.

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (179)
"Located a few miles beyond Hana, this is a well-equipped and very comfortable rental. "
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Set amidst lush greenery, this two-story building offers a serene retreat with a garage and attached structure.

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

10.0 out of 10, Exceptional, (225)
"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
272-6 Puamana 2 Bedroom Oceanfront Remodeled!!
Enjoy a refreshing swim with a view of the ocean from this pool surrounded by palm trees and beach umbrellas.

272-6 Puamana 2 Bedroom Oceanfront Remodeled!!

9.6 out of 10, Exceptional, (67)
"The house was perfect for our needs. Space to spread out our things in the second bedroom and a great kitchen set up. We saw whales every day from our lanai and breakfast table. Loved being able to run and walk in a low speed traffic area. Great centralized location for lots of snorkeling spots. "
272-6 Puamana 2 Bedroom Oceanfront Remodeled!!
Stunning Beach Front Townhouse
Enjoy the ocean view from this balcony with two chairs and a small table.

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (93)
"Firstly, Susan was so wonderful to deal with- thank you for being so welcoming and accommodating- we really appreciated the late checkout- with a 3 year old toddler with us…he was able to nap and that made such a wonderful difference to our last day in paradise. The view is amazing! Would love to stay there again someday soon. "
Stunning Beach Front Townhouse
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.
Enjoy breathtaking ocean views from this balcony with two lounge chairs.

Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.

9.8 out of 10, Exceptional, (35)
"We loved this place will be back again, was great for multiple generations and can’t beat the beach access"
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
Enjoy ocean views from the gazebo, staircase, and deck, surrounded by lush gardens and palm trees.

Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)

9.6 out of 10, Exceptional, (23)
"Here with our family fir a 30th bday"
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
Kihei Maui Beach house - On the water
Enjoy breathtaking views of the ocean from this serene coastal retreat.

Kihei Maui Beach house - On the water

9.8 out of 10, Exceptional, (57)
"Fantastic location. Wonderful pool. Lots of gear to use. It met our expectations. Comfortable space for all 9 of us. Very close to the ocean. We would stay there again. "
Kihei Maui Beach house - On the water
Kaiholo Hale
Enjoy a serene beach experience with turquoise waters and a sandy shore lined with palm trees.

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
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Enjoy a serene retreat with a balcony overlooking the pool and lush surroundings.

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

10.0 out of 10, Exceptional, (16)
"Property was in great location and very clean. Property manager was very nice and very accommodating."
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
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

Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

10/10 Excellent
"Pros- Great place for families. Fun activities for the kids. Short walk to shopping center. Great pool atmosphere for families. Great friendly staff all around. Cons- you will have to walk a bit to get to beach area ideal for laying out. Beach access closest to hotel has a short sand porch. It’s a short walk but keep that in mind. Self parking filled up multiple nights. "
Wendy Erika 5-night trip
Posted 9 hours ago
Hyatt Regency Maui Resort & Spa