Search Villas in Upcountry Maui

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 38 Villas in Upcountry Maui with updated reviews, rates, and availability.

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, (57)
"Great for the two of us to sit outside and enjoy the oasis and gorgeous views from everywhere in the condo. "
The price is AED 874
AED 3,450 total
includes taxes & fees
9 May - 10 May
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
Fridge, microwave, oven, stovetop

Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views

10.0 out of 10, Exceptional, (164)
"Peaceful unobstructed view of Haleakala Lanai and Moloka’i beyond Kahalawai"
The price is AED 1,653
AED 3,661 total
includes taxes & fees
6 May - 7 May
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
~ This Is Wailea Living ~
Point of interest

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (120)
"Great location. Everything just as advertised"
~ This Is Wailea Living ~
Hula On In to Beach House Chic Style, Click the Video tour below!
Outdoor pool

Hula On In to Beach House Chic Style, Click the Video tour below!

10.0 out of 10, Exceptional, (130)
"Condo was very clean, comfortable, and just perfect for our week vacation in Maui with our teen children. Would highly recommend! "
Hula On In to Beach House Chic Style, Click the Video tour below!
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, (74)
"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
Private Ocean Front at Wailea Beach Villas B102
Pool

Private Ocean Front at Wailea Beach Villas B102

10.0 out of 10, Exceptional, (26)
"The unit and property were beautiful. Very spacious and loved being so close to the ocean. Hope to be back again soon. "
Private Ocean Front at Wailea Beach Villas B102
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, (53)
"Property is totally amazing. Wonderful location, amenities and cleanliness. Our family loved our stay. We will return. "
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
May is a Great Time to Play on Maui ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
Pool

May is a Great Time to Play on Maui ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations

10.0 out of 10, Exceptional, (56)
"We had really great time exactly what you see on the photos and in the description thank you very much again"
May is a Great Time to Play on Maui ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (52)
"Had a great time at this place. Tammy was nice and welcoming the place is great. A 1 minute walk to Charlie Young beach. The place is very convenient and well set up for a large group. "
Gated 2-story beach house with big yard
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Exterior

RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

10.0 out of 10, Exceptional, (187)
"This place is just as advertised. We were a family group of 12 people and had a great time. Highly recommend."
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Marriott's Maui Ocean Club, Lāhainā (2BR)
A heated pool

Marriott's Maui Ocean Club, Lāhainā (2BR)

2.0 out of 10, (1)
Marriott's Maui Ocean Club, Lāhainā (2BR)
WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach
Sun loungers, beach towels

WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach

10.0 out of 10, Exceptional, (25)
"I am in love with this property, the location, upgraded comforts and the overall zen I felt while staying there is exactly what I needed this winter. So much to do and see nearby but also tranquil enough to unwind. Highly recommend!!"
WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach
One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~
Outdoor dining

One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~

10.0 out of 10, Exceptional, (70)
"We thoroughly enjoyed our stay at this beautiful villa. We usually stay at The Ritz, however, this was very nearby and allowed us the best of both properties and then some!"
One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~
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, (55)
"We had a wonderful vacation and this location was perfect. After visiting multiple areas in Maui, we decided we like this area best "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Stunning Ocean View at Kapalua Bay Villas
Outdoor dining

Stunning Ocean View at Kapalua Bay Villas

10.0 out of 10, Exceptional, (56)
"Great view. Wonderful place. Lots of fun."
Stunning Ocean View at Kapalua Bay Villas
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
Outdoor pool

Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.

9.8 out of 10, Exceptional, (56)
"We are happy to verify all of Teri’s descriptions as well as previous visitors' comments. ."
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
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, (50)
"Enough space for both my kiddos to stretch out and an amazing view from both lanais. We had a minor issue with the oven the first night and they had maintenance come first thing the next morning to fix the issue. We can't wait to go back to the island. "
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Oceanview Penthouse, sleeps up to 16 guests!
Beach nearby

Oceanview Penthouse, sleeps up to 16 guests!

9.4 out of 10, Exceptional, (15)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!
Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location
Outdoor pool, a heated pool

Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location

10.0 out of 10, Exceptional, (65)
"This place is perfect for 3 couples. Would stay again."
Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location
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, (26)
"It was a great stay and the host was very responsive with any questions we may have had. Aloha and mahalo"
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
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 Maui Kaanapali Villas
Exterior

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2386)
"Absolutely beautiful place to stay, we loved it!!"
The price is AED 765
AED 1,227 total
includes taxes & fees
13 May - 14 May
Aston Maui Kaanapali Villas
Aston Kaanapali Shores
2 outdoor pools, pool umbrellas, sun loungers

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3559)
"Friendly staff, beautiful location."
The price is AED 921
AED 1,195 total
includes taxes & fees
4 May - 5 May
Aston Kaanapali Shores
Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV

Maui Beach Vacation Club

2.5 star property
8.4 out of 10, Very Good, (738)
"Great for family"
Maui Beach Vacation Club
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?
You can expect to pay between AED 874 and AED 1,653 per night for a villa in Upcountry Maui. No matter your budget, a perfect stay is just clicks away on Expedia. 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?
Booking a villa in Upcountry Maui is as easy as working out your travel dates and picking an option that has what you need. In search of something low cost or luxurious, or a stay that also has a kitchenette? Use Expedia’s search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Upcountry Maui?
The quickest way to score cheap villas in Upcountry Maui is with Expedia’s useful filter tool. Narrow your search by star rating, amenities and budget to nab unbeatable prices in only a few keystrokes.