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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 35 Villas in Upcountry Maui with updated reviews, rates, and availability.

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, (76)
"Our family vacation PH H101 this home is the best . Linda is a great host always answered our request we will be back "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (57)
"The house was perfect for our visit with family. There were multiple areas inside and out to relax or spend time in. The grounds were beautiful...even one orchid blooming. "
Gated 2-story beach house with big yard
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, (166)
"Great place !!"
The price is AED 2,332
AED 4,563 total
includes taxes & fees
15 Jun - 16 Jun
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
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, (59)
"we love this area, home was awesome can’t wait to get back to Maui!!"
The price is AED 837
AED 3,393 total
includes taxes & fees
1 Jul - 2 Jul
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
~ This Is Wailea Living ~
Outdoor pool

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (123)
"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, (131)
"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!
Stunning Ocean View at Kapalua Bay Villas
Outdoor dining

Stunning Ocean View at Kapalua Bay Villas

10.0 out of 10, Exceptional, (57)
"Great view. Wonderful place. Lots of fun."
Stunning Ocean View at Kapalua Bay Villas
Maui Resort Rentals: Luana Garden Villas 2D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Pool

Maui Resort Rentals: Luana Garden Villas 2D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

10.0 out of 10, Exceptional, (17)
"It was truly like staying at your new home in Kaanapali. The grill takes some getting used to, but every aspect of Honua Kai was wonderful "
Maui Resort Rentals: Luana Garden Villas 2D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
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, (35)
"Kapalua Golf Villa stay was fantastic! Perfect view, easy walk to beach and pool and nicely decorated condo. Would stay again!"
The price is AED 775
AED 3,292 total
includes taxes & fees
10 Jun - 11 Jun
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
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, (54)
"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
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, (49)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: What a beautiful home! Clean, stunning view, private, easy access to beach and nearby activities and food in Kapalua. Super easy welcome and departing instructions."
The price is AED 775
AED 3,300 total
includes taxes & fees
9 Jun - 10 Jun
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Rare Find! Ocean and Beach Front Cottage!
On the beach

Rare Find! Ocean and Beach Front Cottage!

9.4 out of 10, Exceptional, (3)
"Over all great time. You will loose your parking spot almost every time you leave as it is next to beach access."
Rare Find! Ocean and Beach Front Cottage!
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, (189)
"Nice property, great views. Would stay again. "
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Luxury Oceanview Wailea Retreat [Hōkū Hale]
Property grounds

Luxury Oceanview Wailea Retreat [Hōkū Hale]

The price is AED 2,553
AED 4,603 total
includes taxes & fees
11 Jun - 12 Jun
Luxury Oceanview Wailea Retreat [Hōkū Hale]
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)
"It was good for families with small children and still able to have quiet places for the adults to enjoy. Beautiful property "
Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location
One of our best~ "MAY is On Sale" ~ Must See OCEAN FRONT Villa ~
Outdoor dining

One of our best~ "MAY is On Sale" ~ Must See OCEAN FRONT Villa ~

10.0 out of 10, Exceptional, (71)
"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~ "MAY is On Sale" ~ Must See OCEAN FRONT Villa ~
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, (27)
"family vacation at the this February was exceptional. Easy access to Kapalua Bay. Positioned ideally, the villa offered stunning views of the ocean, golf course, and mountains. The host was friendly, attentive, and provided convenient amenities that ensured our comfort throughout the trip. Top-choice destination for our family, highly recommend it to those seeking a serene and fulfilling Maui escape."
WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Outdoor pool

5 Star Ocean View, Beach House Chic, Click the Video tour below!

10.0 out of 10, Exceptional, (87)
"Great host had a lovely time thank you so much!"
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Welcome to Honua Kai Luana upstairs Oceanfront Resort Resort POOL view
On the beach, sun loungers, beach towels

Welcome to Honua Kai Luana upstairs Oceanfront Resort Resort POOL view

7.4 out of 10, Good, (3)
"We were a family of 6 (3 college aged and 1 HS). Beautiful place! We loved having the pool right outside the door and the beach just a short walk away. It’s right across the street from a grocery store which was super convenient. Would definitely be on our list if we come back to Maui!"
Welcome to Honua Kai Luana upstairs Oceanfront Resort Resort POOL view
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, (56)
"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!
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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Frequently asked questions

How much do villas in Upcountry Maui cost?
You can expect to pay between AED 775 and AED 2,553 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.