Search Vacation Homes in Upcountry Maui

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Compare 92 Vacation Homes in Upcountry Maui with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, (335)
"Well first off Hana is absolutely beautiful and a shame most people just drive out for the day. Staying in this lovely VRBO rental was really a charm. Cute place in a very quiet secluded area. Just a wonderful stay. Next time book for longer. "
The price is SAR 732
SAR 1,490 total
includes taxes & fees
27 Nov - 28 Nov
Fisher's Hana Bay Hale, Across from Hana Bay
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, (328)
"Short walk to Hāna Bay. Cottage is roomy, well appointed, and matches photos and description. Have stayed there twice and would definitely stay there again. There are few options for dinner in Hāna, so bringing your own food is recommended. "
STHA-2017/0002 Across from Hana Bay
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (58)
"After staying here for a 3rd time, I decided to leave a review. This is such a fantastic home in the best location on Maui. We LOVE having the private beach in our own backyard, plenty of space to gather as a family with privacy in the bedrooms if we want it. The teens work out in the fitness center, the kids play in the pool and the adults lay out on the beach, all without leaving! Thank you so much"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
9.2 out of 10, Wonderful, (135)
"Hana is a sleepy town ...but friendly ...everything is in walking distance...need more vacation time!"
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
10.0 out of 10, Exceptional, (124)
"This place was amazing! The view and pool were spectacular as advertised . Close to all the great beaches. We had an amazing stay and will be back!"
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
10.0 out of 10, Exceptional, (77)
"We had a wonderful time staying at the Umalu location. It was conveniently located right next to the highway so it was easy access to get around the island. And it was only a 5 minute drive down the street from the beach. The hosts, Kelly and Dan were so nice and made us home made banana bread to welcome us and also shared some great dining locations for us to visit during our stay. "
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Beautiful Home in paradise!
9.6 out of 10, Exceptional, (156)
"Beautiful view, great front deck for breakfast! Appreciated the Kona coffee provided. Could use a few more mugs as we are all coffee drinkers! Nice to have beach towels, chairs and boogie boards. The master bath was roomy and beautiful. Price was very reasonable. Thank you for the wonderful stay "
Beautiful Home in paradise!
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
10.0 out of 10, Exceptional, (3)
"After looking at dozens of home for rent, we decided on this property and do not regret the decision. It’s beautifully appointed with brand new furniture, plenty of room for a large group (we had 16) and my goodness, that beach across the street, divine! There are several areas to dine, a gorgeous pool with pool and beach toys included, and what felt like a private concierge with the manager (who lives close by). Thank you for an unforgettable vacation with my family. We will cherish the...
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
10.0 out of 10, Exceptional, (160)
"We loved our stay here - the home is cozy and the views are amazing. We enjoyed paddleboarding with turtles and seeing them not only on the beach and in the water but from the house as well. The owner and property manager were great and responsive, the home is older, but very well kept and clean. Absolutely would stay here again! No AC, but open windows and fans cooled the place down nicely, especially at night. Would highly recommend!"
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
9.8 out of 10, Exceptional, (205)
"This is our 3rd time booking this property and every time has been amazing! The house is perfect for our family of four. It has always been very clean, quiet and relaxing. The property is so gorgeous and we enjoy our time out on the patio. 1000000000 X would recommend! If this is your first time to Hana, I recommend bringing or buying bug spray as it is the jungle and there are lots of bugs outside. You’ll be totally fine if you have some though. See you next year Hana!"
The price is SAR 1,126
SAR 2,371 total
includes taxes & fees
3 Dec - 4 Dec
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Mountain to Ocean Views Pole House @ Maui Adventure Villa
9.8 out of 10, Exceptional, (206)
"We were amazed at the warmth and decor and incredible views from this beautiful home We would not hesitate to return. Jeff and Beth"
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
10.0 out of 10, Exceptional, (28)
"Very clean… all the amenities. Loved the pool, deck and movie room. Kurt was an amazing host! Would definitely be back. "
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Private gated home with 300 Foot private beach front, beach toys and much more!
10.0 out of 10, Exceptional, (53)
"Are you looking for the premier stay in all of Maui? Look no further than this amazing beach house. We stayed here for 7 days in August, and fell in love with all this place has to offer. The entire house was spotlessly clean, with plenty of towels and toiletries. The bedrooms each have their own climate control, the beds are all super comfortable, and all bedrooms have stunning views of the ocean. We spent a great deal of time watching the waves and turtles from the sitting area off the kitchen...
Private gated home with 300 Foot private beach front, beach toys and much more!
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
9.8 out of 10, Exceptional, (138)
"Wonderful location with plenty of amenities to make for a great Maui vacation. In-laws booked the 2nd unit next door and we had a wonderful time hanging out on the large deck. Would absolutely book again."
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, (42)
"The place was Amazing! Super close to the ocean, to food & restaurants- Perfect place to stay! Best Family Vacation Ever!!!"
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
9.8 out of 10, Exceptional, (68)
"We had a very relaxing time at this property! Such a beautiful place. We will definitely stay again. "
The price is SAR 3,041
SAR 5,039 total
includes taxes & fees
30 Nov - 1 Dec
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Hana Ocean Palms Bungalows
9.6 out of 10, Exceptional, (106)
"The Ocean Palms Bungalow is the perfect vacation home on the road to Hana. It is set back and hidden from the road and is surrounded by beautiful trees and a lush garden. I stayed at a similar cottage years ago but that home was sold and taken off the rental market. I have been searching for another like it for years but nothing has ever compared until now. The house is not a sleek, modern place with all new matchy- matchy furniture. But that is exactly what makes this place so special. It...
Hana Ocean Palms Bungalows
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
9.6 out of 10, Exceptional, (78)
"We came to Hawaii to visit our son and grandchildren who live in Maui. This home was perfect for our needs, well stocked, and the pool area was fantastic."
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, (63)
"Fabulous spot for a family with kids (3, in our case). Quiet neighborhood just a few minutes away from great food and stores. Plenty of space in the house and a cute backyard to boot. Incredibly easy to walk to the beach (crosswalk and access path). Good spot for day trips north and west. A+"
Spacious Hawaiian home 50 steps from Sugar Beach!
BEACHFRONT MAUI KIHEI HOUSE
9.8 out of 10, Exceptional, (150)
"This house was absolutely perfect for our family. We had 10 people staying and we all fit very comfortably. The beds were nice, they have ac units in all of the rooms which was great for our family with different temperature needs. The yard was so much fun for our toddlers to run and play in and the beach is a very short walk away. We all really enjoyed relaxing at the house. We needed a pack and play for our toddler and a newborn and while we brought one we also depended on the one available at...
BEACHFRONT MAUI KIHEI HOUSE
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

Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3350)
"We had an excellent time staying three nights at the Aston! We ate at the restaurant and it was great. The amenities are great and the staff went above and beyond our expectations. We used the concierge for booking a luau and it was fantastic. Five stars all around! "
The price is SAR 1,216
SAR 1,546 total
includes taxes & fees
1 Dec - 2 Dec
Aston Kaanapali Shores
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2627)
"Nice and smooth experience. I recommend it!"
The price is SAR 826
SAR 2,963 total
includes taxes & fees
9 Dec - 10 Dec
OUTRIGGER Honua Kai Resort & Spa
The Westin Ka'anapali Ocean Resort Villas
4.0 star property
8.6 out of 10, Excellent, (1080)
"Loved the shuttle to whalers village. Had to request housekeeping service twice during our stay as our room was missed ?"
The price is SAR 1,798
SAR 2,121 total
includes taxes & fees
29 Nov - 30 Nov
The Westin Ka'anapali Ocean Resort 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.