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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 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, (55)
"Great location- quiet at night, super clean, very comfortable bed, loved the roomy shower! We loved having coffee along outside on the patio while watching for whales. Don't forget your binoculars! It was lovely to use the folding chairs supplied when we walked over to Kapalua Bay beach to snorkel and swim. We also loved being able to walk to the shops/restaurants/walking trails near the Ritz. Nice to make some of our own meals along with dining out. We had a wonderful stay and plan to...
The price is AED 1,017
AED 3,659 total
includes taxes & fees
9 Apr - 10 Apr
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, (163)
"The home itself is a sanctuary and was hard to leave daily as we went out and explored the island but always looked forward to it in the evening. The mornings were equally amazing. Host was easy to get in touch with and answered questions quickly. Will definitely seek it out again when we return"
The price is AED 1,653
AED 3,661 total
includes taxes & fees
14 Apr - 15 Apr
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)
"We really enjoyed our stay in this condo. It was clean and the primary bed was very comfortable. Communication with the host was smooth and efficient. The AC worked great. Beach/pool towels and portable chairs were provided, which was great. As a note, though, I would have really appreciated a cooler and umbrella for the beach. I’d definitely recommend this place to a couple or small family. "
~ 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, (129)
"We loved the condo! Really cleaning well organized. Great space, location and amenities. It has everything you need for a great get away. Groceries, restaurants and beautiful all within 5 min. Thank you for your home away from home."
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, (72)
"We felt so removed from all the hustle bustle of daily life. Our villa was amazing. It had everything we needed and more. We all had such a good time. "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
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
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)
"My family and I planned this trip back in March 2024 and reserved this property in Ho'olei.Right from the initial reservation process and first payment installment, the interaction with Matthew was excellent and seamless. Matthew was responsive and very helpful.The unit at Ho'olei was remarkable, well located within the property, and most importantly, was extremely clean when we checked in. There was a small welcome gift which was appreciative. The unit was very well equipped with all we needed,...
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Open & REDUCED 4/5- 4/14 ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations
Pool

Open & REDUCED 4/5- 4/14 ~ NICE OCEAN FRONT Villa ~ Newer AC ~ Platinum Maui Vacations

10.0 out of 10, Exceptional, (56)
"We found this unit comfortable and well outfitted for our needs. Enjoyed the views over the water and walking the trail.along the water's edge. Spectacular. Easy access to good restaurants too!"
The price is AED 1,319
AED 2,786 total
includes taxes & fees
20 Apr - 21 Apr
Open & REDUCED 4/5- 4/14 ~ 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, (51)
"Our family of 6 thoroughly enjoyed this house. Situated within walking distance of a great beach and close to plenty of shopping, you couldn’t ask for a better location. The property is fenced in which allows for privacy and a sense of security. There are plenty of amenities in the house including surfboards, boogie boards, chairs and an umbrella for the beach, bikes a ping pong table, a hammock and much more. We had a great time and would stay there again in a heartbeat!"
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, (186)
"Amazing family vacation!"
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)
The price is AED 3,669
AED 4,215 total
includes taxes & fees
15 Apr - 16 Apr
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, (24)
"What can we say - it was 10/10 all around - amazing luxurious place with all the amenities and very responsive host. There is nothing to complain other than that we are going to miss staying here "
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, (68)
"Loved it! Beautiful view!!!"
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, (53)
"Overall this property was perfect. Had everything we needed for our family vacation (6 adults, 3 children). Property was clean, located close to pool and beach, shopping close by, we’d definitely stay here again in the future. "
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, (55)
"Absolutely stunning property. Private pool, love birds and other birds galore. Property is as listed. Watch the whales from the pool deck. We hung out at the pool all the time. Totally private. Terri was wonderful to work with. She kept in touch during our stay. She also stocked our suite with bananas, mango and other treats. The outside shower is to die for. "
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)
"Perfect Maui getaway. Went for my Bach party with 10 of my best friends. Fabulous neighboorbood. Great safe location. Close to all the beaches and luxury restaurants. "
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)
"Impeccably beautiful home. All one level, so spacious, bright and well appointed. Easy walk to pools and beach. Washer/dryer much appreciated. Large lanai, room for all. Beach chairs etc made time at the beach easy. (We opted not to have property manager stop by to show us a few things. Would recommend you have him visit when you arrive (to demonstrate things like TV, cooktop…) Such an easy welcome vacation. "
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)
"This property was exactly as described and complete perfection as it related to housing all of our family members. The grounds are beautiful. The pool is gorgeous. The location for us was exactly where we wanted to be and just across the street from the beach. We did have some street noise coming from behind the patio but it wasn't terribly intrusive. The kitchen was well stocked with dishes and utensils as well as small appliances. The Furnishings are modern which included a fair amount of...
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, (2379)
"This is my 2nd time staying here was a great overall experience. Room was clean no bugs or little critters. Kitchen makes it easy to make your own meals to save money. Will definitely stay here again highly recommend "
The price is AED 827
AED 1,301 total
includes taxes & fees
9 Apr - 10 Apr
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, (3524)
"Had everything we needed, laundry in the room was great. Nice balcony and kitchen. "
The price is AED 843
AED 1,103 total
includes taxes & fees
14 Apr - 15 Apr
Aston Kaanapali Shores
Sands of Kahana 354
Condo, Multiple Beds (Sands of Kahana 354) | Beach/ocean view

Sands of Kahana 354

4.0 star property
Sands of Kahana 354
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 1,017 and AED 3,669 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.