Search Villas in Upcountry Maui

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Compare 26 Villas in Upcountry Maui with updated reviews, rates, and availability.

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!

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

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-

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

9.8 out of 10, Exceptional, (36)
"This is our second stay at the Golf Villas of Kaplua and of course, the location of the property is wonderful. Clean property, enjoyed the view and convenience of the shuttle, which unfortunately will no longer be provided effective Jan. 2025. There is a unit above this one, so some noise from those guests early each morning unfortunately. We weren't able to use the room safe, as it needed a battery per the property management, but it was not fixed during our stay. "
Last Minute Deal! (11/22- 12/4) ~ PLATINUM Maui Vacations ~ TROPICAL OASIS

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

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

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

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

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

Book 5 Nights, Get 6th Free + Late Check-Out!

10.0 out of 10, Exceptional, (8)
"This was the best location, easy to get to beach and mall"
Book 5 Nights, Get 6th Free + Late Check-Out!

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

9.6 out of 10, Exceptional, (28)
"This is a beautiful villa. Amazing ocean view. Plenty of room for 2 of us. Kitchen has basics everything you need for breakfast, lunch and simple dinner. Bed is comfortable and enjoyed the spacious bathroom. Host was available about my inquiry. Look forward to staying here again. Mahalo "
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!

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!

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!

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

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

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!

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

9.4 out of 10, Exceptional, (62)
"This was our second time staying in this unit, and it was just as great as the first. Perfect location, well-priced, and comes as advertised. Will continue to recommend for anyone staying on Maui!"
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

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

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

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)
"Several people we visited were “owners” at AKS and were very friendly; one even said “thank you for staying at Shores; I hope you make the choice to stay here again.” The view out our balcony of the pool area and the ocean from afar was beautiful. "
The price is SAR 1,329
SAR 1,679 total
includes taxes & fees
8 Dec - 9 Dec
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2627)
"Some things were not working in our room, e.g. master bedroom balcony door would not open, table in the balcony was very wobbly, dryer was not operating properly. All these issues were resolved by the staff when I called them, but they seem to be basic checks that property management should have checked before giving us keys and not have me call about them. "
The price is SAR 826
SAR 2,963 total
includes taxes & fees
10 Dec - 11 Dec
OUTRIGGER Honua Kai Resort & Spa

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1080)
"Great property in perfect location adjacent to walking path & snorkeling beach. We loved our one-bedroom unit and enjoyed the resorts amenities including pools and restaurants. Well maintained, very clean, friendly staff, wish we could have extended our stay, but not easy to do at a timeshare property like you can at a hotel. That said, we wouldn't hesitate to return, next time for a longer visit. Mahalo!"
The price is SAR 1,798
SAR 2,121 total
includes taxes & fees
4 Dec - 5 Dec
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.

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. Vacationing 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.