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Compare 33 Villas in Upcountry Maui with updated reviews, rates, and availability.

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (44)
"The house is amazing, providing the perfect atmosphere for quality time with my family. All slept well, felt at home and enjoyed every moment. Thank you!"
Gated 2-story beach house with big yard

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

Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

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."
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

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

9.6 out of 10, Exceptional, (49)
"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!

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

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

9.8 out of 10, Exceptional, (51)
"Overall really enjoyed the property. The pictures were a little misleading in that it looks like there is grass surrounding the lower balcony but it is rock landscaping not grass. Was a little disappointed as we specifically booked the property for the grass area that our baby could crawl on. Besides that we enjoyed the stay and the kapalua area was amazing! Loved the beaches. Was great being so close to the pool"
The price is SAR 1,069
SAR 3,617 total
includes taxes & fees
4 Mar - 5 Mar
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain

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

10.0 out of 10, Exceptional, (30)
"Everything about our stay at this property was amazing. Easy check in, great responsiveness from the Host, and the condo was just as great as the pictures. Our family of 8 adults had plenty of room and really enjoyed everything about our rental. "
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

9.8 out of 10, Exceptional, (43)
"wonderful, relaxing near privacy - not front row yet calming"
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

One of our best OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

10.0 out of 10, Exceptional, (67)
"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 OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

Oceanview Penthouse, sleeps up to 16 guests!

9.4 out of 10, Exceptional, (14)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!

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

Marriott's Maui Ocean Club, Lāhainā (3BR)

2.0 out of 10, (1)
"This was my Christmas present to my children this year and with just hours before our flight on Christmas Day, I got an email not a phone call an email telling me that our reservation was canceled with no explanation as to why. I spent three hours with four different managers, trying to figure out how to save Christmas for my kids as I was flying from Denver all the way over nonstop to Maui, Hawaii for our Christmas vacation. This was a disaster that VRBO allows owners to cancel with no...
The price is SAR 11,248
SAR 12,786 total
includes taxes & fees
10 Feb - 11 Feb
Marriott's Maui Ocean Club, Lāhainā (3BR)

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

10.0 out of 10, Exceptional, (68)
"Great property and location. Would come back and rent anytime."
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

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

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

The price is SAR 3,747
SAR 4,246 total
includes taxes & fees
20 Feb - 21 Feb
Marriott's Maui Ocean Club, Lāhainā (2BR)

Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa

9.8 out of 10, Exceptional, (72)
"Great Christmas with our whole family! Nice to come where there is plenty of room inside and out. It was beautiful! Thank you!"
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa

Maui Resort Rentals: 6 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!

10.0 out of 10, Exceptional, (11)
"After many years of trying to stay in Maui with the entire family we successfully booked and enjoyed all of the amenities of the Villas. The three bedrooms were spacious, the kitchens have upgraded equipment and when the microwave in one unit and the A/C in the other unit, the Maui management company was quick to resolve by bringing in portable units. The units came with a garage so you could store your extra items if needed, however the Villas had vast storage for all of our clothes and...
Maui Resort Rentals: 6 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!

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

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

10.0 out of 10, Exceptional, (34)
"Great property, awesome location, nice staff, helpful concierge, beautiful view!!! "
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
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, (3451)
"We had a great stay at this beautiful property. Enjoyed watching the whales from our balcony. Highly recommend! "
The price is SAR 1,459
SAR 1,832 total
includes taxes & fees
27 Feb - 28 Feb
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2691)
"Surf, whales, gracious staff, Beautifully landscaped We will definitely return to the Outrigger Hanoa Kai"
The price is SAR 1,625
SAR 3,904 total
includes taxes & fees
23 Feb - 24 Feb
OUTRIGGER Honua Kai Resort & Spa

Kaanapali Alii

4.0 star property
9.4 out of 10, Exceptional, (859)
"Beautiful accommodations."
Kaanapali Alii
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 SAR 1,069 and SAR 11,248 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.