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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (44)
"The house is amazing, providing the perfect atmosphere for quality time with my family. All slept well, felt at home and enjoyed every moment. Thank you!"
Gated 2-story beach house with big yard
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Pool

EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

10.0 out of 10, Exceptional, (25)
"Positive"
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
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, (48)
"The property was very nice. Great location. Very clean. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
Pool

Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

9.6 out of 10, Exceptional, (67)
"Beautiful villa with all of the accommodations needed for a wonderful holiday. Perfectly located to get to all that Wailea offers."
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
Pool

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

9.8 out of 10, Exceptional, (50)
"Great for the two of us to sit outside and enjoy the oasis and gorgeous views from everywhere in the condo. "
OCEANFRONT gated Kapalua Bay Villa 23G1. Steps to beach!
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Aerial view

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

9.8 out of 10, Exceptional, (42)
"This was the most relaxing stay in the ideal location. Beautiful home, breathtaking views, and the most comfortable accommodations. It was simple check in process and stress-free. Can’t wait to come back!"
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Spectacular Ka'anapali Villa 3/3, AC, pool, Ocean and Island views
Beach nearby, beach umbrellas

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

9.8 out of 10, Exceptional, (50)
"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
One of our best OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations
Outdoor dining

One of our best OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations

10.0 out of 10, Exceptional, (65)
"We had a wonderful experience. The kitchen had everything you could need. The rooms were well kept and the views were great. The outdoor patio was a favorite spot. The grounds in this complex were manicured so nicely and very clean."
One of our best OPEN- 2/16- 2/19 ~ Must See OCEAN FRONT Villa ~ PLATINUM Maui Vacations
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Pool

Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!

10.0 out of 10, Exceptional, (30)
"Everything about our stay at this property was amazing. Easy check in, great responsiveness from the Host, and the condo was just as great as the pictures. Our family of 8 adults had plenty of room and really enjoyed everything about our rental. "
The price is HK$5,061
HK$16,781 total
includes taxes & fees
28 Jan - 29 Jan
Maui Resort Rentals: Luana Garden Villas 8D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
Luxury 3-Bedroom Wailea Beach Villa M312
Pool

Luxury 3-Bedroom Wailea Beach Villa M312

10.0 out of 10, Exceptional, (9)
"This was the best location, easy to get to beach and mall"
Luxury 3-Bedroom Wailea Beach Villa M312
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Aerial view

OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!

9.6 out of 10, Exceptional, (31)
"Kitchen was sparse, no place to put luggage, no Kleenex in bathrooms. Check out to early 10am Kitchen garbage can sitting in dining area. Have stayed in Kapalua for years and most Villas were more generously appointed. "
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Oceanview Penthouse, sleeps up to 16 guests!
Beach

Oceanview Penthouse, sleeps up to 16 guests!

9.6 out of 10, Exceptional, (13)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Pool

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

10.0 out of 10, Exceptional, (53)
"My family and I planned this trip back in March 2024 and reserved this property in Ho'olei.Right from the initial reservation process and first payment installment, the interaction with Matthew was excellent and seamless. Matthew was responsive and very helpful.The unit at Ho'olei was remarkable, well located within the property, and most importantly, was extremely clean when we checked in. There was a small welcome gift which was appreciative. The unit was very well equipped with all we needed,...
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Outdoor pool, an infinity pool

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

10.0 out of 10, Exceptional, (67)
"This our favorite place to stay on Maui. Lovely, well-maintained condo with an ocean view and quick walk to pools and the beach. We spent some time every day at the adult pool, which is a quiet, beautiful setting. The gym was well-equipped. Linda was a responsive and terrific host. Despite a series of thunderstorms with 70mph winds that knocked out power our last night, we can't wait to return!"
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Beach nearby, sun-loungers, beach towels

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

9.6 out of 10, Exceptional, (64)
"Nice unit. We enjoyed our stay and hope to come back someday soon. The unit was in a quiet area near everything Maui has to offer. The complex was quiet and clean. We would stay again. "
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Outdoor pool, a heated pool

I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (25)
"This place was exceptional - beautiful home, well appointed, location could not be better! We loved walking to the beach and so many terrific restaurants. Appreciated having some beach equipment there (few beach chairs, one small umbrella, couple of snorkel masks). Pool was also lovely and relaxing - not a zoo like at the resorts. Lots of great space for our family of 8 (all adults). Easy check in. Geoff was very responsive and helpful. Would love to stay here again!!"
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
SUPER SPECIAL (1/10- 1/24) AS LOW AS $199 ~ Platinum Maui Vacations ~ TROPICAL OASIS
Outdoor dining

SUPER SPECIAL (1/10- 1/24) AS LOW AS $199 ~ Platinum Maui Vacations ~ TROPICAL OASIS

9.8 out of 10, Exceptional, (38)
"This is a very nice property with elevated views over the golf course and ocean beyond. It is spacious, comfortable and very well equipped with high end appliances. Would definitely stay here again."
SUPER SPECIAL (1/10- 1/24) AS LOW AS $199 ~ Platinum Maui Vacations ~ TROPICAL OASIS
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
An infinity pool

Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla

10.0 out of 10, Exceptional, (34)
"Great property, awesome location, nice staff, helpful concierge, beautiful view!!! "
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa
Pool

Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa

9.8 out of 10, Exceptional, (72)
"Great Christmas with our whole family! Nice to come where there is plenty of room inside and out. It was beautiful! Thank you!"
Maui Resort Rentals: Marriott's Maui Ocean Club 3 Bedroom Oceanfront Villa
Luana Garden Villa 6D @ Honua Kai Resort Kaanapali
Pool

Luana Garden Villa 6D @ Honua Kai Resort Kaanapali

10.0 out of 10, Exceptional, (10)
"Highly recommend this beautiful villa. Stocked with everything you could want to make your vacation seamless. Dennis and Monty are super responsive hosts! Will definitely stay here again on our next trip to Maui!"
Luana Garden Villa 6D @ Honua Kai Resort Kaanapali
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?
Villas in Upcountry Maui range between HK$5,061 and HK$5,061 per night. These getaways give you the privacy to enjoy your own space at a price that’s gentle to your wallet. 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?
With Expedia, it’s easy to find your dream villa in Upcountry Maui. Holidaying with the kids? Use our handy filters to look for stays with amenities like WiFi and a pool. If you have a set budget, click on how much you’re willing to spend and your preferred star rating. We’ll help you find the perfect place that suits your style and taste.
How can I find cheap villas in Upcountry Maui?
Expedia is here to help you easily source cheap villas in Upcountry Maui. Use the filter tool to select budget, amenities and star rating to refine your search and find an awesome place to stay in just a few clicks.