Search Villas in Upcountry Maui

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Villas in Upcountry Maui and around

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

10.0 out of 10, Exceptional, (177)
"Great place !!"
The price is €872
includes taxes & fees
22 Aug - 23 Aug
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

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

9.6 out of 10, Exceptional, (63)
"Beautiful home in a prime location. Was perfect for our family of 4 to go back and forth between Maui. Clean, cute decor, beautiful view of the ocean. Has a small private beach, little rocky hike for the kids to explore, friendly neighbors. Gated quiet community. Would stay here again "
The price is €856
includes taxes & fees
19 Aug - 20 Aug
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!

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

9.6 out of 10, Exceptional, (37)
"Kapalua Golf Villa stay was fantastic! Perfect view, easy walk to beach and pool and nicely decorated condo. Would stay again!"
The price is €858
includes taxes & fees
2 Sept - 3 Sept
Kapalua Bay 1BR Villa | Oceanfront, Gated, Molokai Views & Beach Access 29B4

Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning

3.5 star property
8.0 out of 10, Very good, (1)
The price is €942
includes taxes & fees
20 Aug - 21 Aug
Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning

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

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

Kapalua Bay Villa 29b4 1 Bedroom Villa by RedAwning

3.5 star property
The price is €948
includes taxes & fees
17 Sept - 18 Sept
Kapalua Bay Villa 29b4 1 Bedroom Villa by RedAwning

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

9.8 out of 10, Exceptional, (50)
"We had a great time!"
The price is €858
includes taxes & fees
1 Sept - 2 Sept
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

Lovely 2 Bed/2 Bath Ohana Hale - Steps from the Beach

9.4 out of 10, Exceptional, (13)
"What an amazing place to stay. We were not expecting the recent remodel and have to say they have done a wonderful job. Excellent location close to some wonderful beaches and great dining options. Great kitchen made it easy to save money and prepare our own meals."
Lovely 2 Bed/2 Bath Ohana Hale - Steps from the Beach

Beach Hideaway 2bedroom/2bath Steps to the Sand with BONUS Family Room

10.0 out of 10, Exceptional, (7)
"Great spot in part of a larger complex. Good communication with host. Great location. "
Beach Hideaway 2bedroom/2bath Steps to the Sand with BONUS Family Room

Poolside Bungalow 2 Bedroom/2 Bath with Bonus Family Room

Poolside Bungalow 2 Bedroom/2 Bath with Bonus Family Room

Villas By The Cove, Ocean View 2 Bedroom Villa Steps To The Beach

9.8 out of 10, Exceptional, (70)
"Fantastic location in Kihei. Onsite amenities (e.g., pool, yoga, washer/dryer) enhanced our stay. Even with other guests at the property, it was quiet and relaxing."
Villas By The Cove, Ocean View 2 Bedroom Villa Steps To The Beach

Villas By The Cove, Villa 1 · Go for an Ocean Swim From a Fun Beach Villa

9.8 out of 10, Exceptional, (71)
"Great location..clean rooms..great pool"
Villas By The Cove, Villa 1 · Go for an Ocean Swim From a Fun Beach Villa

Villas By The Cove, Villa 8 · 1 Bedroom Villa with Ocean Views, Steps to Beach

9.8 out of 10, Exceptional, (72)
"Had a nice time, close to beach and restraunts."
Villas By The Cove, Villa 8 · 1 Bedroom Villa with Ocean Views, Steps to Beach

Villas By The Cove, Villa 2 · 1 Bedroom Beach Villa Steps to the Sand

9.8 out of 10, Exceptional, (59)
"Lovely private complex, close to the beach and restaurants. Perfect for our anniversary trip."
Villas By The Cove, Villa 2 · 1 Bedroom Beach Villa Steps to the Sand

Villas By The Cove, Villa 9 · Walk to Cove Beach Park from a Refined Villa

9.8 out of 10, Exceptional, (48)
"This villa was perfect for what we were looking for on our honeymoon! It was secluded and affordable and in an amazing location where we could walk to everything"
Villas By The Cove, Villa 9 · Walk to Cove Beach Park from a Refined Villa

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (128)
"Fantastic property."
~ This Is Wailea Living ~

The Westin Nanea Ocean Villas (1BR)

The Westin Nanea Ocean Villas (1BR)

The Westin Nanea Ocean Villas (2BR)

The Westin Nanea Ocean Villas (2BR)

The Westin Nanea Ocean Villas (3BR)

4.0 out of 10, (2)
"On Christmas evening, I had just finished cleaning up after dinner and was preparing to pack my bag. We would be departing for the airport at 4:30am the next morning. I checked my email around 6:30pm and noticed an email from the host of this unit, that I had booked months before. The email stated that my booking (which was to start the next day) was being cancelled and I would get a refund in 8-10 days. I am 5 months pregnant, and was traveling with 4 children. My immediate thought was that...
The Westin Nanea Ocean Villas (3BR)

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

The Westin Kā‘anapali Ocean Resort Villas (Studio Premium)
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upcountry Maui Hotel Reviews

Frequently asked questions

How much do villas in Upcountry Maui cost?
You can expect to pay between €872 and €2,889 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.