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Featured Villas in Upcountry Maui

Our top choices for Upcountry Maui villas

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

10.0 out of 10, Exceptional, (177)
"Great place !!"
The price is AU$1,795
includes taxes & fees
5 Sept - 6 Sept
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

STEEP PRICE DROP Now thru September ~ Must See OCEAN FRONT Bay Villa ~

10.0 out of 10, Exceptional, (72)
"Excellent location and appointed house! It was a wonderful place to stay. Loved it and you will to!"
STEEP PRICE DROP Now thru September ~ Must See OCEAN FRONT Bay Villa ~

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

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

10.0 out of 10, Exceptional, (82)
"Everything was great! Can’t wait to come back. "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

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

10.0 out of 10, Exceptional, (67)
"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

The Westin Nanea Ocean Villas (2BR)

The price is AU$1,313
includes taxes & fees
17 Sept - 18 Sept
The Westin Nanea Ocean Villas (2BR)

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (131)
"Fantastic property."
The price is AU$818
includes taxes & fees
5 Sept - 6 Sept
~ This Is Wailea Living ~

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

10.0 out of 10, Exceptional, (194)
"Amazing family vacation!"
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

K L V R presents Beautiful Ground floor Villa 1A at Honua Kai Resort,

10.0 out of 10, Exceptional, (24)
"We have stayed here a few times now and we have never been disappointed. It's a lovely property. This is our first time staying in the Villa. We loved the space. One thing I wished was that they have maid service such as in the towers but otherwise it was great. "
K L V R presents Beautiful Ground floor Villa 1A at Honua Kai Resort,

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

9.6 out of 10, Exceptional, (61)
"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!

MODERN HAWAII ⛳️ Modern Remodel, steps to the Beach, 4th Tee, Ocean View, 4 Pools

10.0 out of 10, Exceptional, (64)
"We usually stay on the beach, but this condo on the golf course was a lovely change of pace. The setting was peaceful, with breathtaking views of the trees, birds, and greens. The European furnishings were tasteful and elegant, adding to the overall charm of the space.The open floor plan was airy and fantastic, and the patio doors that fully open made the living area feel expansive and connected to the outdoors. We especially loved having two patios—one for morning sun and the other for...
MODERN HAWAII ⛳️ Modern Remodel, steps to the Beach, 4th Tee, Ocean View, 4 Pools

Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

10.0 out of 10, Exceptional, (71)
"Wonderful accommodations, great location and friendly staff!"
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

Welcome to Honua Kai Luana upstairs Oceanfront Resort Resort POOL view

8.0 out of 10, Very good, (4)
"This listing is such a great stay and worth the price. Everything is new and updated and there are so many options - the beach, the pool or all the other pools! We want to stay again! Two things that would be nice to know ahead of time; 1. The condo is up a flight of stairs and there is no elevator, so elder guests may have issues accessing the Unit. And 2. The condo pool is saltwater, which is something my kids had to get used to. "
Welcome to Honua Kai Luana upstairs Oceanfront Resort Resort POOL view

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (63)
"Close to beaches and has great amenities such as surfboards, bikes, etc."
Gated 2-story beach house with big yard

Ho'olei Garden View by Coldwell Banker Island Vacation

2.0 star property
Ho'olei Garden View by Coldwell Banker Island Vacation

Stunning Ocean View at Kapalua Bay Villas

10.0 out of 10, Exceptional, (60)
"Unit was perfect..super clean,well equipped, amazing views and beach,quiet...i could go on and on. We stayed next door a few years ago and feel this is the best place to staybin maui. We will hopefully be back again. Thanks! "
Stunning Ocean View at Kapalua Bay Villas

Welcome to Luana Garden Villas 3B & 3D

10.0 out of 10, Exceptional, (22)
"Great for a family stay."
Welcome to Luana Garden Villas 3B & 3D

Kapalua Bay 1BR Villa | Oceanfront, Gated, Molokai Views & Beach Access 29B4

9.6 out of 10, Exceptional, (38)
"Kapalua Golf Villa stay was fantastic! Perfect view, easy walk to beach and pool and nicely decorated condo. Would stay again!"
The price is AU$1,484
includes taxes & fees
17 Sept - 18 Sept
Kapalua Bay 1BR Villa | Oceanfront, Gated, Molokai Views & Beach Access 29B4

Spectacular 3rd Row Villa at Ho'olei with Ocean Views

10.0 out of 10, Exceptional, (57)
"We had an amazing time. Will be coming back again! "
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

10.0 out of 10, Exceptional, (55)
"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
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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Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Find out more about Upcountry Maui

Upcountry Maui Villas information

Number of reviews
Accommodation
40 Villas
Lowest Price
AU$818
Highest Price
AU$1,795

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Explore a world of travel with Expedia

Frequently asked questions

How much do villas in Upcountry Maui cost?
Prepare to pay between AU$818 and AU$1,795 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.