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Compare 121 Vacation Homes in Upcountry Maui with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (356)
"We are grateful to the host for renting their beautiful home to us. The kitchen was well equipped with everything we needed to cook meals. The home is well ventilated with lots of windows and screens to prevent bugs from entering. Great location near the beach and the grocery store was a few minutes away. "
Fisher's Hana Bay Hale, Across from Hana Bay

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (93)
"Had a wonderful 7 days in Kihei - this place was great. Loved that you could walk the beautiful beach, the grounds were very well maintained, the pool was delightful and my husband was able to walk to the city park and play pickleball every morning. "
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

9.0 out of 10, Wonderful, (40)
"Pumana was a beautiful area. We arrived just before a huge storm and the 2nd night of our stay there was a leak in the ceiling from the heavy rain fall. We got in touch with the property manager and he helped us move to a different property. We were thankful for his help and kindness. We were extremely happy with our stay. "
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

10.0 out of 10, Exceptional, (127)
"Very spacious house with a delightful pool. Walk to a nice beach good for kids. Convenient location. Loved it!"
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (67)
"We had a fantastic time! Everything was even better than we expected. We only wish we’d had a little more sunshine"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

Stunning Beachfront Private Home! Perfect for Families, Great Location!

9.8 out of 10, Exceptional, (93)
"11 family members stayed at this property. Beautiful yard, view of ocean, access to beach, great location."
Stunning Beachfront Private Home! Perfect for Families, Great Location!

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"This was an amazing property! It’s in a great location, spacious rooms and awesome amenities. Our group loved playing pickleball and heading to the beach with all of the provided beach equipment. Host was attentive as well, we would definitely recommend to anyone looking for a luxurious and relaxing vacation. "
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

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

10.0 out of 10, Exceptional, (8)
"Beautiful"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

10.0 out of 10, Exceptional, (63)
"We stayed in Kahana with our children and their families. Six adults and three kids under 6 in this beautifully styled, waterfront property. The condo was beautifully and thoughtfully appointed with everything we needed. Clean, quiet and modern unit situated on a beautiful property. Pool and grounds are spotless and offer magnificent views of the islands, whale spouts and swimming sea turtles. Our hosts were helpful, considerate and easy to communicate with. Thank you Tracy and Steve for a...
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (171)
"Great quiet location. Listen to the ocean and the birds. "
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

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

10.0 out of 10, Exceptional, (89)
"We had a great stay! It started with a walkthrough of the house to understand how to work everything and learn where everything was. Any time we needed help the communication was prompt and very easy. Any small issues were immediately remedied. The beds were fairly comfortable and the house was very aesthetically pleasing. The view from the roof was nice and the pool was very clean. We would definitely rent from them again!"
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (192)
"We were a family of eight adults and six children ages seven and under. The pool and yard were amazing. We used all of the open areas inside and out but really loved the huge covered lanai. We also rented the Ohana unit for one of our little families. They appreciated the quiet down there. Note that you must go outside to reach it, but we didn’t mind. House was very well stocked with beach towels/regular towels and paper products. The beach is so convenient and undeveloped. We rented wagons and...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

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

10.0 out of 10, Exceptional, (6)
"A "great room" inside for a large group and lots of lovely outdoor space around the pool makes for a perfect spot to bring your family. I had 11 and the five grandkids - ages 25-16 in one big room and all the adults in nice rooms for each couple. Just a short walk to the beach and a great little coffee shop. Kids are asking to come again! Thanks for making a memory for all of us."
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

9.6 out of 10, Exceptional, (57)
"The stay was great. "
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (160)
"Very spacious! 10 min short trip from Hana and 5 min to waianapanapa state park"
Beautiful Home in paradise!

Secluded Ocean View Napili Home - Sleeps 14

10.0 out of 10, Exceptional, (57)
"House was great for extended family trip."
Secluded Ocean View Napili Home - Sleeps 14

Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

9.8 out of 10, Exceptional, (79)
"The front door was almost impossible to unlock. WE had to have the owner come twice to try to fix it. He decided that we should leave it unlocked when we were away since the key wouldn't work. It caused a lot of stress."
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

105-1 Puamana Spacious Townhome Near Ocean.

9.4 out of 10, Exceptional, (52)
"We checked out of this beautiful condo three days before the Maui fires. It was one of those places where we for sure will come back to. As far as I can tell, it is still standing, but the clubhouse and some surrounding buildings did burn. This is the most amazing location on the island. Will definitely be back hopefully to help rebuild, and for sure to enjoy the beauty."
105-1 Puamana Spacious Townhome Near Ocean.

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"Gem 45 min from airport hidden in cliffs with beautiful view of coast , sunrise and waterfall . It beats multiple destination sightseeing spots on the island !"
Waterfall House - Private House Overlooking the Ocean!

Private gated home with 300 Foot private beach front, beach toys and much more!

10.0 out of 10, Exceptional, (59)
"What a great place!! We had a mini-family reunion with our adult children(7) and toddler/baby grandchildren (3). Check-in was a breeze, Daniel kept in touch before, during and after. The house is right on the water, the beach is right there--sitting on the patio, even the whales cooperated by providing us with a show every day. The stairs down to the beach are steep, but our toddler had no problems navigating. We were generally the only people on the beach, the water is shallow and warm.In...
Private gated home with 300 Foot private beach front, beach toys and much more!
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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Other property types in Upcountry Maui

Hawaiian Dream Temple

4.0 star property
Hawaiian Dream Temple

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3464)
"Great views. Pleasant staff"
The price is AED 1,139
AED 1,451 total
includes taxes & fees
25 Feb - 26 Feb
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2349)
"Beautiful well kept grounds Two nice pools"
The price is AED 1,120
AED 1,646 total
includes taxes & fees
2 Mar - 3 Mar
Aston Maui Kaanapali Villas
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.