Search Villas in Upcountry Maui

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Browse Select Upcountry Maui Villas

Outdoor pool, an infinity pool
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
10.0 out of 10, Exceptional, (55)
"We had an amazing stay!!! Everything was perfect! The location is sooooo perfect! Will definitely be back!"
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Pool
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
10.0 out of 10, Exceptional, (46)
"It was an amazing stay"
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
A heated pool
Hawaii Life Vacations Hoolei Wailea Lux Residence Overlooking Resort Pool
10.0 out of 10, Exceptional, (21)
"The property is located in an ideal location. Right in the heart of restaurants and shops. The beach is right across the street. The unit is high end. The beds were comfortable and we enjoyed the lanai every morning and night."
Hawaii Life Vacations Hoolei Wailea Lux Residence Overlooking Resort Pool
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Outdoor pool, a heated pool
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
10.0 out of 10, Exceptional, (19)
"Walking distance to wailea beach and shops, comfortably fit 10 people. Walkable to fantastic pool as well. Only issue was a couple things were broken from tennants before us, but property manager remedied critical items."
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Property grounds
Steep $ Drop in May ~ MUST SEE ~ PLATINUM Maui Vacations ~ OCEAN FRONT Villa
10.0 out of 10, Exceptional, (63)
"Great place for your family. Views are incredible, short walk to the beach, owner is very responsive and everything was as or better than expected."
Steep $ Drop in May ~ MUST SEE ~ PLATINUM Maui Vacations ~ OCEAN FRONT Villa
Pool
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
10.0 out of 10, Exceptional, (21)
"My experience at this villa was nearly perfect, thanks to its immaculate condition, breathtaking views, and unparalleled beach access. Every morning, the sight from the villa was a serene start to the day, and the easy access to the beach made my stay exceptionally relaxing and enjoyable. The concierge service was also noteworthy, providing excellent recommendations and assistance throughout my visit. However, a notable service mishap occurred regarding checkout. Despite all written materials...
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Pool
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
10.0 out of 10, Exceptional, (26)
"Fantastic place. Very clean"
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Aerial view
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
9.8 out of 10, Exceptional, (41)
"Incredible view from the giant bay windows where we were able to whale watch. Huge bathroom. Well equipped kitchen. Very comfortable bed and well-decorated accommodations. Our only warning would be that if you have a serious fear of bugs and critters, choose a room that’s on a higher floor. We did have 5 cockroaches visit over our 3 day stay (and one small frog!)"
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Pool
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa
9.8 out of 10, Exceptional, (70)
"Such a beautiful and functional space. We had an excellent stay!"
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa
Pool
AMAZING LOCATION in the HEART of WAILEA!! WBV H102!
9.8 out of 10, Exceptional, (55)
"The condo and property are beautiful. The condo was fully stocked with everything we needed which was appreciated. It was not an issue for us but the walk to the pool could be difficult for some people as there is a hill to the pool/beach area. We had a great stay and enjoyed many parts of Maui."
AMAZING LOCATION in the HEART of WAILEA!! WBV H102!
Beach nearby
New Ka'anapali Deluxe Villa Ocean and Island view
9.8 out of 10, Exceptional, (47)
"A great and quiet property."
New Ka'anapali Deluxe Villa Ocean and Island view
Outdoor dining
Lowest Price in Years! ~ PLATINUM Maui Vacations ~ TROPICAL OASIS ~ Clean & Affordable
9.8 out of 10, Exceptional, (33)
"This was our third stay at the Kapalua Golf Villas. As always we had a great stay. This property was clean and well appointed with everything we needed to enjoy the beach. Free door to beach shuttles made it so easy to get to the beach with all our gear for snorkeling. We always cook in and the kitchen had all the necessities. We had a great view of the golf course and multiple pools close by to choose from. We only wish that our stay was longer. Looking forward to our next trip."
Lowest Price in Years! ~ PLATINUM Maui Vacations ~ TROPICAL OASIS ~ Clean & Affordable
An infinity pool
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
9.8 out of 10, Exceptional, (28)
"Great property, service with amazing snorkeling. Pools and exercise facility perfect. The two bedroom suite with kitchen with view to Lanai and an accordion sliding door to patio…amazing! The Royal Ka’anapali golf course was terrific as well and offers challenge for low index players. Will definitely stay here again."
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
Pool
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
9.6 out of 10, Exceptional, (35)
"My wife and I recently stayed here for a weeklong getaway from reality. We’ve stayed in this neighborhood before and loved it with our entire family. This time we came just the two of us and this one bedroom condo was the perfect size for us. Beautiful place with beautiful views."
The price is £572
per night
17 May - 18 May
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
A waterfall pool
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
9.6 out of 10, Exceptional, (39)
"All good with this residence. Location great grounds beautiful. Had a few minor issues with air conditioning unit as was not working properly upon arrival. It took 2 days to fix. They were diligent and resolved. Key cards kept demagnetizing and had to be replaced twice. Other than those 2 minor issues would definitely recommend."
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Aerial view
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
9.6 out of 10, Exceptional, (26)
"Location was great with lots of pristine beaches and snorkeling spots close by. The villa itself was clean and easy to access. Some of the patio furniture was worn from the elements but that was about it. Overall a great area to stay in if you like a quiet relaxing place."
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Pool
Maui Resort Rentals: 6 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!
9.6 out of 10, Exceptional, (9)
"The unit was set up very well, loved the two master setup. The location was nice. Would have liked a larger living room area, and maybe a ground level, rather than two raised garden levels."
Maui Resort Rentals: 6 Total Bedrooms at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!
Beach
Oceanview Penthouse, sleeps up to 16 guests!
9.4 out of 10, Exceptional, (10)
"First time in Hawaii, came with family and friends: this house is just spectacular… great vibe, awesome location. Beds are comfortable, just great!"
Oceanview Penthouse, sleeps up to 16 guests!
Pool
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
9.4 out of 10, Exceptional, (62)
"My family and I enjoyed the stay at this beautiful and fully equipped unit. The location of this unit was close to the pool and is walking distance to the Wailea mall and beach. I would definitely give 5 stars, but I was disappointed to find the floors and kitchen counter top weren’t the cleanest upon arrival. The counter had sand or something of that texture on it and the floors were dirty. We had a problem with the cable box and/or router, but since it was our last evening there, we just let...
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
Don't see what you're looking for?
See all available properties in Upcountry Maui
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.

Other property types in Upcountry Maui

Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1469)
"Very nice and very well taking care of "
The price is £593
per night
4 Jun - 5 Jun
Aston Mahana at Kaanapali
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2531)
"I loved everything about this resort. "
OUTRIGGER Honua Kai Resort & Spa
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2998)
"Amazing views and right on the beach and pools were never packed "
The price is £268
per night
27 May - 28 May
Aston Kaanapali Shores
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.

Upcountry Maui Villas information

Number of reviews
559
Accommodation
21 Villas
Lowest Price
£572
Highest Price
£572

Frequently asked questions

Why book your holiday villa in Upcountry Maui with Expedia?
Expedia makes it simple to find your ideal holiday villa in Upcountry Maui. Holidaying with the family? Use our filters to look for stays with amenities like a pool. If you’re sticking to a budget, click on how much you want to spend and your preferred star rating. We’ll help you find the perfect fit that gels with your taste and style.
How can I find cheap villas in Upcountry Maui?
With Expedia’s user-friendly filter tool, scoring cheap villas in Upcountry Maui is a piece of cake. To find properties that will keep some cash in your pocket, tailor your search results by star rating, budget and amenities.

Upcountry Maui Hotel Reviews
Expedia verified reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

5/5 Excellent
"I usually visit Oahu twice a year and decided to give Maui a try. I thought nothing could top Oahu but I was wrong. I absolutely loved everything about my trip and I think a huge reason was this hotel. The staff were incredibly friendly and even remembered my name. Helene at front desk was especially great. Room was clean and newly renovated. The beach was so beautiful, gardens and hammocks offered were so nicely kept, also great restaurant and store on site. You definitely get your moneys worth booking this resort. What I also really loved about this resort was the free cultural activities offered. I was able to make my own lei and it was such a great experience. Overall this hotel is so amazing and I cant wait to visit again."
A verified traveller stayed at OUTRIGGER Kaanapali Beach Resort
Posted 2 days ago
OUTRIGGER Kaanapali Beach Resort