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Featured Villas in Upcountry Maui

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (46)
"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, (50)
"We had a conference at the Grand Wailea and were bringing our adult children. This rental is very close to the hotel for a go between to attend the conference and catch up with our children at the end of the day. We stayed at the rental with them when the conference was over. Short walk to the shops and beach!Great layout for everyone to have their own space. "
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, (52)
"we love this area, home was awesome can’t wait to get back to Maui!!"
The price is AU$1,517
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!

9.8 out of 10, Exceptional, (31)
"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, (44)
"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 AU$5,462
includes taxes & fees
19 Feb - 20 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, (69)
"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

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 AU$1,829
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, (3457)
"The resort had easy access to various beaches and the amenities were great! "
The price is AU$674
includes taxes & fees
18 Mar - 19 Mar
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2344)
"We stayed in a main floor villa which siuted us well. Liked the access from parking of not having to climb stairs. We enjoyed the on site restaurant....very convenient. "
Aston Maui Kaanapali Villas

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2699)
"This property was absolutely perfect for our big group of 20! Management got our rooms all on the same side of the property. The gathering space outside on the green was wonderful for playing spike ball and throwing a football. The beach out front was beautiful! My kids loved the different pool options! We also loved that we could walk to the food truck park and grocery story. The proximity to other beaches was also great! We had the best time at Black Rock Beach nearby."
The price is AU$1,566
includes taxes & fees
12 Mar - 13 Mar
OUTRIGGER Honua Kai Resort & Spa
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?
Prepare to pay between AU$1,517 and AU$5,462 per night for a villa in Upcountry Maui. No matter your budget, an ideal getaway is only a click away on Expedia. This price was 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.