Search Villas in Upcountry Maui

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Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (40)
"We had a great time in Kihei and the place was perfect for my family. The yard was amazing and we could walk to the beach!"
Gated 2-story beach house with big yard

OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!

9.6 out of 10, Exceptional, (28)
"Exactly what we wanted. The area, Kapalua is exceptional the place clean, very roomey, everything I needed was in the kitchen ,bathroom, and very comfortable King bed. Definitly will stay here again. Great parking, close to pool, and resturants. 5 stars across the board"
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!

Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-

9.6 out of 10, Exceptional, (66)
"Everything was fabulous from our contact with Monica to get us checked in and deliver packages shipped from home to the beautiful accommodation to the pool to the location. We will be back with our family of 8 very soon."
Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-

OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

9.8 out of 10, Exceptional, (47)
"We like this part of Maui is its lesser crowded and has great beaches close by. Property is in a nice location with view of ocean. "
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

10.0 out of 10, Exceptional, (24)
"The unit and property were beautiful. Very spacious and loved being so close to the ocean. Hope to be back again soon. "
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

Oceanview Penthouse, sleeps up to 16 guests!

9.6 out of 10, Exceptional, (13)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!

Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

9.6 out of 10, Exceptional, (47)
"The property was very nice. Great location. Very clean. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

DISCOUNTED Availability left to years end ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

10.0 out of 10, Exceptional, (64)
"Had a great time. No problems that were insurmountable. Easy access. In all a good time"
DISCOUNTED Availability left to years end ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla

10.0 out of 10, Exceptional, (31)
"Beautiful property overlooking the ocean, clean, modern, great location, nice amenities. "
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla

Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa

9.8 out of 10, Exceptional, (70)
"Such a beautiful and functional space. We had an excellent stay!"
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa

Aloha Villas Resort | 12 Bed, 12.5 Bath

9.8 out of 10, Exceptional, (43)
"No detail, communication or service was less than spectacular. From the fully equipped villas to games and lush greenery, we enjoyed our home in paradise for two weeks. Thank you to Jude and Mary for promptly responding to our needs throughout our stay."
Aloha Villas Resort | 12 Bed, 12.5 Bath

Paradise for Two ~ LAST SPOT LEFT> 11/20- 12/1 ~ Platinum Maui Vacations Villa ~ ALL 5 STARS ~

10.0 out of 10, Exceptional, (57)
"This home is the perfect size and location for a couple looking for a clean, thoughtfully decorated, well appointed and comfortable stay in Kapalua. This is one of the nicest, well appointed, homes we have stayed in. The owners have gone to great lengths to bring the Hawaiian Ohana feels into their home to share with guests. I would recommend this stay to any couple looking for a clean, stylish, relaxing place with an incredible golf course and ocean view. The property manager, Dave, was...
Paradise for Two ~ LAST SPOT LEFT> 11/20- 12/1 ~ Platinum Maui Vacations Villa ~ ALL 5 STARS ~

Spectacular 3rd Row Villa at Ho'olei with Ocean Views

10.0 out of 10, Exceptional, (51)
"Communication prior to going was easy and thorough. Condo was lovely and clean and well equipped. Property grounds were beautiful and very well maintained, with a gorgeous pool and gym. If issues came up response was quickly handled...there are many battery operated blinds in the home that need charging prior to guests' arrival. One of the blinds didnt work and it was fixed that evening. The view is spectacular from the upper sitting area! Property itself is up a hill, across from the...
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

9.8 out of 10, Exceptional, (42)
"This was the most relaxing stay in the ideal location. Beautiful home, breathtaking views, and the most comfortable accommodations. It was simple check in process and stress-free. Can’t wait to come back!"
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

10.0 out of 10, Exceptional, (51)
"Wrong entry code for property gate. Snuck in with a car who went around us. Never received a “personal code” to actually enter the unit. Waited in garage for a return call that thankfully granted us access Everything was great after that except that only one card worked for the unit out stay. "
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

New Ka'anapali Deluxe Villa Ocean and Island view

9.8 out of 10, Exceptional, (49)
"Loved staying in this property and the proximity to a great beach with adjacent parking. Appreciated all the beach chairs and snorkel gear that was available to use. Can’t wait to return to paradise! "
New Ka'anapali Deluxe Villa Ocean and Island view

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

10.0 out of 10, Exceptional, (65)
"We were there for our 50th anniversary with family- 4 adults and 2 children! Great location, beautiful condo "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (23)
"We love the house. It was perfect for the family. The only downside was the master bedroom is very warm compared to the rest of the house. Also, there is mold in the master bathroom shower but overall it was a great place to stay. The pool is very nice And the location can’t be beat. "
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

Last Minute Deal! (11/22- 12/4) ~ PLATINUM Maui Vacations ~ TROPICAL OASIS

9.8 out of 10, Exceptional, (36)
"Very pretty and clean vacation. It was our first time and the property manager was soooooo sweet and understanding…. 10/10 recommend. Future trips will definitely be booked again!"
Last Minute Deal! (11/22- 12/4) ~ PLATINUM Maui Vacations ~ TROPICAL OASIS

Luana Garden Villa 6D @ Honua Kai Resort Kaanapali

10.0 out of 10, Exceptional, (8)
"Absolutely loved everything about this condo. Gorgeous, well maintained property, ideal location, a short walk to pools and beach. Having 3 bedrooms and 3 bathrooms was ideal with 4 teenagers. Loved the huge back patio and how spacious and well stocked the condo was. Teens loved having access to the workout facilities. Very nice grocery store and shopping down the road. Hope to come back again someday! "
Luana Garden Villa 6D @ Honua Kai Resort Kaanapali
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 HK$2,522
HK$3,204 total
includes taxes & fees
24 Nov - 25 Nov
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 HK$1,712
HK$6,142 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 HK$3,728
HK$4,398 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.
Beautiful view of the beach with palm trees

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Frequently asked questions

How much do villas in Upcountry Maui cost?
Villas in Upcountry Maui range between and per night. These getaways give you the privacy to enjoy your own space at a price that’s gentle to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your villa in Upcountry Maui with Expedia?
With Expedia, it’s easy to find your dream villa in Upcountry Maui. Holidaying with the kids? Use our handy filters to look for stays with amenities like WiFi and a pool. If you have a set budget, click on how much you’re willing to spend and your preferred star rating. We’ll help you find the perfect place that suits your style and taste.
How can I find cheap villas in Upcountry Maui?
Expedia is here to help you easily source cheap villas in Upcountry Maui. Use the filter tool to select budget, amenities and star rating to refine your search and find an awesome place to stay in just a few clicks.