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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Upcountry Maui

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Relax in the open-air lounge with a round table and comfortable seating, surrounded by tropical views and ceiling fans.

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

10.0 out of 10, Exceptional, (80)
"Everything was wonderful… thank you so much Linda."
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
Relax by the resort's inviting pool surrounded by lush greenery and palm trees, with sun loungers and umbrellas providing ample shade.

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
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Relax in this serene outdoor seating area with wicker sofas and a round table, perfect for enjoying a glass of wine and a snack.

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

10.0 out of 10, Exceptional, (176)
"Great place !!"
The price is AU$1,555
includes taxes & fees
8 Aug - 9 Aug
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Relax by the serene pool surrounded by lush gardens and palm trees, with a stunning ocean view.

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
Stunning Ocean View at Kapalua Bay Villas
Enjoy a romantic meal on this oceanfront balcony with a stunning view of palm trees and the distant shoreline.

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
~ This Is Wailea Living ~
Enjoy meals al fresco on this outdoor balcony with a garden view.

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (128)
"Fantastic property."
The price is AU$856
includes taxes & fees
4 Sept - 5 Sept
~ This Is Wailea Living ~
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Enjoy the ocean views and cityscape from this balcony with comfortable wicker furniture.

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
MODERN HAWAII ⛳️ Modern Remodel, steps to the Beach, 4th Tee, Ocean View, 4 Pools
Relax on the spacious balcony with a sofa, ottoman, and table, taking in the views of the well-maintained lawn.

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
Gated 2-story beach house with big yard
Stroll through the serene surroundings of this single-story home, surrounded by mature trees and a well-manicured lawn.

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (62)
"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
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Relax in style on this spacious patio with a round table, six chairs, and a grill area, surrounded by lush greenery and a clear view.

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

9.6 out of 10, Exceptional, (60)
"This condo was perfect! Very clean and accommodating for our group! The host was very quick to respond and the condo was in a great location! We will be back"
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Relax on the spacious balcony with a sofa and two chairs, taking in the lush landscape and distant ocean views.

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
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
Relax on the spacious balcony with a sofa and enjoy the serene views of the lush tropical garden.

Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades

10.0 out of 10, Exceptional, (55)
"We met up with our family fromAustralia and had a wonderful time here in Maui. The condo was very well maintained and well stocked which made for a pleasant experience. Would highly recommend. "
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Traditional home surrounded by lush tropical plants and a manicured lawn.

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
STEEP PRICE DROP Now thru September ~ Must See OCEAN FRONT Bay Villa ~
Relax in this ocean-view area with a round table, chairs, and a small table for refreshments.

STEEP PRICE DROP Now thru September ~ Must See OCEAN FRONT Bay 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!"
STEEP PRICE DROP Now thru September ~ Must See OCEAN FRONT Bay Villa ~
Rare Find! Ocean and Beach Front Cottage!
Relax in a serene oceanfront setting with comfortable lounge chairs under a shaded pergola.

Rare Find! Ocean and Beach Front Cottage!

9.0 out of 10, Wonderful, (4)
"We stayed a week in this cute beach front cottage. It is central located with walking distance to restaurants, surfing lessons, groceries and shops. The owner/host was easily get in touch with and accommodated us with early check in since we had a very early flight in. The view is beautiful and we watched sunset every day from our lanai. "
The price is AU$1,246
includes taxes & fees
9 Aug - 10 Aug
Rare Find! Ocean and Beach Front Cottage!
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!
Relax and socialize in this inviting balcony area with comfortable seating, a grill, and stunning views of the resort.

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!
Marriott's Maui Ocean Club, Lāhainā (3BR)
Relax on the beachfront lawn with a gazebo, lounge chairs, and lush greenery.

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$5,163
includes taxes & fees
7 Aug - 8 Aug
Marriott's Maui Ocean Club, Lāhainā (3BR)
Ho'olei Garden View by Coldwell Banker Island Vacation
Enjoy a scenic view from this balcony with a dining table for four and comfortable seating.

Ho'olei Garden View by Coldwell Banker Island Vacation

2.0 star property
Ho'olei Garden View by Coldwell Banker Island Vacation
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Relax on the balcony with a glass floor offering unobstructed views of the lush surroundings, accompanied by comfortable wicker seating and a ceiling fan for ventilation.

Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views

9.6 out of 10, Exceptional, (54)
"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
Welcome to Luana Garden Villas 3B & 3D
Relax on the patio with a dining table for two, comfortable seating, and a grill for outdoor cooking.

Welcome to Luana Garden Villas 3B & 3D

10.0 out of 10, Exceptional, (20)
"Great for a family stay."
Welcome to Luana Garden Villas 3B & 3D
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?
Prepare to pay between AU$856 and AU$5,163 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.