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Villas in Upcountry Maui

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Villas in Upcountry Maui

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

Kula
10.0 out of 10, Exceptional, (185)
"Great stay"
United States
Peter A.
$874 nightly
The price is $1,017
Dec 9 - Dec 10
Total with taxes and fees
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

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

Lahaina
9.8 out of 10, Exceptional, (50)
"We had a great time!"
United States
Ryan N.
$803 nightly
The price is $913
Dec 9 - Dec 10
Total with taxes and fees
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

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

Lahaina
9.6 out of 10, Exceptional, (69)
"Great location. "
United States
Justin B.
$811 nightly
The price is $923
Dec 13 - Dec 14
Total with taxes and fees
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

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

Lahaina
9.6 out of 10, Exceptional, (42)
"Gorgeous view and off the beaten track enough that you felt very relaxed. Staying in Kaanapali is very congested and Kapalua Bay is so much better. "
United States
Lori O.
$876 nightly
The price is $998
Dec 9 - Dec 10
Total with taxes and fees
Kapalua Bay 1BR Villa | Oceanfront, Gated, Molokai Views & Beach Access 29B4

Kapalua Bay Villa 29b4 1 Bedroom Villa by RedAwning

3.5 star property
Lahaina
$974 nightly
The price is $1,149
Dec 9 - Dec 10
Total with taxes and fees
Kapalua Bay Villa 29b4 1 Bedroom Villa by RedAwning

Stunning Ocean View at Kapalua Bay Villas

Kapalua
10.0 out of 10, Exceptional, (67)
"What a beautiful place! We loved the area, the views, and the comfortable unit. "
United States
Katie M.
$624 nightly
The price is $731
Jan 5 - Jan 6, 2026
Total with taxes and fees
Stunning Ocean View at Kapalua Bay Villas

Villas By The Cove, Villa 5 · Exquisite Ocean View Villa with Pool across from the Beach

South Kihei
9.2 out of 10, Wonderful, (42)
"Great Location, easy booking, unit is getting tired but would stay there again."
United States
Joseph F.
$712 nightly
The price is $828
Dec 25 - Dec 26
Total with taxes and fees
Villas By The Cove, Villa 5 · Exquisite Ocean View Villa with Pool across from the Beach

Luxury Oceanview Wailea Retreat with Sunset Views

Wailea
$1,097 nightly
The price is $1,276
Dec 19 - Dec 20
Total with taxes and fees
Luxury Oceanview Wailea Retreat with Sunset Views

Rare Find! Ocean and Beach Front Cottage!

South Kihei
9.4 out of 10, Exceptional, (6)
"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. "
United States
Na W.
$1,180 nightly
The price is $1,372
Jan 5 - Jan 6, 2026
Total with taxes and fees
Rare Find! Ocean and Beach Front Cottage!

The Westin Nanea Ocean Villas (2BR)

Lahaina
$942 nightly
The price is $947
Dec 11 - Dec 12
Total with taxes and fees
The Westin Nanea Ocean Villas (2BR)

The Westin Kā‘anapali Ocean Resort Villas (Studio Premium)

Lahaina
$1,126 nightly
The price is $1,132
Dec 11 - Dec 12
Total with taxes and fees
The Westin Kā‘anapali Ocean Resort Villas (Studio Premium)

Marriott's Maui Ocean Club, Lāhainā (1BR)

Lahaina
$650 nightly
The price is $654
Dec 11 - Dec 12
Total with taxes and fees
Marriott's Maui Ocean Club, Lāhainā (1BR)

The Westin Nanea Ocean Villas (1BR)

Lahaina
$816 nightly
The price is $820
Dec 20 - Dec 21
Total with taxes and fees
The Westin Nanea Ocean Villas (1BR)

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

Lahaina
5.4 out of 10, (3)
"The property manager did not tell us we would have to change rooms part way through our trip. They also did not coordinate the move. They also did not communicate with the front desk on our arrival and our room was not clean. We were not able to use half the facility on the first night. The check in desk has the owner’s name on the reservation, and then added ours. The facility was great and staff was great, the host was hard to work with."
United States
Leslie C.
$839 nightly
The price is $843
Dec 11 - Dec 12
Total with taxes and fees
Marriott's Maui Ocean Club, Lāhainā (2BR)

Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning

3.5 star property
Lahaina
8.0 out of 10, Very Good, (1)
$885 nightly
The price is $1,044
Dec 9 - Dec 10
Total with taxes and fees
Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning

The Westin Nanea Ocean Villas (3BR)

Lahaina
4.0 out of 10, (2)
"We had booked a 3 bedroom VRBO way in advance for my husband and adult daughter and son. We wanted to stay togerther in one unit. 3 days before we were traveling from the states to Hawaii, we were informed by the host that "the owner was being difficult" and we were not allowed to stay in the unit we booked! They wanted us to cram into a 2 bedroom villa which meant one of the adults would have to sleep on a pull out couch! NOT acceptable. After much discussion, the best they were able to do was...
United States
Sue H.
$1,503 nightly
The price is $1,511
Dec 11 - Dec 12
Total with taxes and fees
The Westin Nanea Ocean Villas (3BR)

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

Lahaina
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...
United States
Nancy F.
$1,256 nightly
The price is $1,263
Dec 11 - Dec 12
Total with taxes and fees
Marriott's Maui Ocean Club, Lāhainā (3BR)

Kapalua Bay Vill 23g1 Ocean Front 1 Bd/1ba 1 Bedroom Villa by RedAwning

3.5 star property
Lahaina
$894 nightly
The price is $1,055
Dec 13 - Dec 14
Total with taxes and fees
Kapalua Bay Vill 23g1 Ocean Front 1 Bd/1ba 1 Bedroom Villa by RedAwning
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

Upcountry Maui Villas information

Number of reviews
386
Accommodation
53 Villas
Lowest Price
$654
Highest Price
$1,511

Frequently asked questions

How much do villas in Upcountry Maui cost?
You can expect to pay between $654 and $1,511 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.

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