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Compare 28 Villas in Upcountry Maui with updated reviews, rates, and availability.

Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (41)
"Reviews I read hinted at how wonderful this place is and it's true and then some. The grounds, furnishings, equipment, kitchen, and everything you would want in a home to be comfortable were there. So many nice touches and if you want to cook some or all of your meals, you will have no problem having everything you need include a BBQ grill. I only wish we had more time to make use of all the house had to offer. The beach is just a three minute walk to the south and two minute walk to the north...
Gated 2-story beach house with big yard
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Outdoor pool, an infinity pool

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

10.0 out of 10, Exceptional, (66)
"First trip to Maui - Loved our time at this condo! Thank you Linda! 1. Communication: from the outset, Linda’s communication was outstanding and fast which in my mind is always a good indication. 2. Location: Perfect for the Shops at Wailea and Beach. The condo is adjacent to all the shops in Wailea and you can literally walk from the condo right into all the shops, restaurants, coffee, etc. There is a gate at the condo that connects you right into the shops. The beach is a 2 min walk...
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
Pool

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

9.8 out of 10, Exceptional, (50)
"Great for the two of us to sit outside and enjoy the oasis and gorgeous views from everywhere in the condo. "
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Aerial view

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
Pool

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

10.0 out of 10, Exceptional, (52)
"Lots of room especially if you are multi family. Having your own bathroom and large kitchen, dining, living room and lanai is wonderful. Pool is amazing, grounds are very well kept. Within walking distance to the Shops of Wailea and Wailea Beach. Have stayed several times before and have never been disappointed!"
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Beach nearby, beach umbrellas

Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views

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! "
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
An infinity pool

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

10.0 out of 10, Exceptional, (32)
"Facilities were clean and beautiful "
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Pool

Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

10.0 out of 10, Exceptional, (29)
"Loved our stay. Already planning our next one. Property was amazing and so were the property managers. "
The price is ￥101,602
￥336,895 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-
Pool

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

9.6 out of 10, Exceptional, (67)
"Beautiful villa with all of the accommodations needed for a wonderful holiday. Perfectly located to get to all that Wailea offers."
Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-
Two January Stays Still Open ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
Pool

Two January Stays Still Open ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations

10.0 out of 10, Exceptional, (55)
"Just as described: ocean views, nice pool right out front, updated decor, good space for a couple. We used the barbeque grills at the pool twice, and it was easy. Comfortable bed, roomy master bath. Loved having the Coastal Trail so close for walking. Kapalua is an upscale area with a beautiful beach. Easy to walk to the Montage or Ritz Carlton for their restaurants. "
Two January Stays Still Open ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Aerial view

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

9.6 out of 10, Exceptional, (31)
"Property was more than we expected. Super clean great location."
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Oceanview Penthouse, sleeps up to 16 guests!
Beach

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!
A waterfall pool

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

9.6 out of 10, Exceptional, (48)
"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!
Beach nearby, sun loungers, beach towels

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

9.4 out of 10, Exceptional, (63)
"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
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (24)
"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
One of Our BEST- OPEN & REDUCED- 12/16- 12/24 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations
Outdoor dining

One of Our BEST- OPEN & REDUCED- 12/16- 12/24 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

10.0 out of 10, Exceptional, (65)
"We had a wonderful experience. The kitchen had everything you could need. The rooms were well kept and the views were great. The outdoor patio was a favorite spot. The grounds in this complex were manicured so nicely and very clean."
One of Our BEST- OPEN & REDUCED- 12/16- 12/24 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations
Open & Reduced (1/13- 2/1) ~ PLATINUM Maui Vacations ~ TROPICAL OASIS
Outdoor dining

Open & Reduced (1/13- 2/1) ~ 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. "
Open & Reduced (1/13- 2/1) ~ PLATINUM Maui Vacations ~ TROPICAL OASIS
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa
Pool

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
Pool

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

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

10.0 out of 10, Exceptional, (25)
"Positive"
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
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

OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2648)
"Very nice unit with a layout that served our needs well. A few problems that were not addressed, even though reported. The master bath shower heads did not operate correctly and remained a dribble for showers. My husband says the splitter was broken. There were ants in the laundry room. It would have been nice if the kitchen was better equipped. It was lacking basics and we cook a fair amount. We had to buy items such as cutting board, measuring cups, and a knife that was actually sharp enough...
The price is ￥71,012
￥155,493 total
includes taxes & fees
Jan 10 - Jan 11, 2025
OUTRIGGER Honua Kai Resort & Spa
Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3392)
"Great place to stay at west Maui. Many good snorkeling places. Easy access to beach. Property includes a laundry, grocery just cross street with good poke."
The price is ￥62,368
￥78,181 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Aston Kaanapali Shores
Royal Kahana Maui by OUTRIGGER
Condo, 2 Bedroom, Oceanfront (Unit 410, 2Bath) | Terrace/patio

Royal Kahana Maui by OUTRIGGER

3.0 star property
8.0 out of 10, Very Good, (1323)
"The room was well designed with a great view of the ocean. It had cooking facility and excellent for a linger stay. The rooms have mirrors which helps with light view and makes the room bigger. The rooms also had a washer dryer and together made our stay comfortable and enjoyable"
Royal Kahana Maui by OUTRIGGER
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 ￥101,602 and ￥101,602 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.