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Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Upcountry Maui condo rentals

Living area
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (76)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
$511 nightly
The price is $598
Jan 11 - Jan 12, 2026
Total with taxes and fees
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Property grounds
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (111)
"Everything Good "
United States
Marc
$511 nightly
The price is $598
Jan 9 - Jan 10, 2026
Total with taxes and fees
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
On the beach
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (23)
"I would stay again "
United States
Bruce H.
$488 nightly
The price is $571
Jan 9 - Jan 10, 2026
Total with taxes and fees
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Beach towels
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (196)
"Very quiet safe place. "
Canada
Monica
$381 nightly
The price is $446
Jan 6 - Jan 7, 2026
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Exterior
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (267)
"Great stay"
United States
Noah C.
$325 nightly
The price is $380
Jan 9 - Jan 10, 2026
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Outdoor pool, a heated pool
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
North Kihei
10.0 out of 10, Exceptional, (125)
"Very nice condo Nice furniture Comfortable and friendly "
United States
John
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
Property grounds
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.6 out of 10, Exceptional, (159)
"Everything was great. Kitchen well stocked, beautiful view. "
United States
Eric S.
$320 nightly
The price is $373
Dec 22 - Dec 23
Total with taxes and fees
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
On the beach
Best Oceanfront Value in Kihei - Kealia Resort!

Best Oceanfront Value in Kihei - Kealia Resort!

Best Oceanfront Value in Kihei - Kealia Resort!
North Kihei
9.6 out of 10, Exceptional, (109)
"The condo was exactly as described and in a great location, we loved the grassy area right in front of the beach if we didn’t feel like sitting in the sand! Tim had all the essentials for us and was quick to respond if we had any questions- we would definitely stay here again in the future! "
United States
Bailey B.
$378 nightly
The price is $440
Dec 20 - Dec 21
Total with taxes and fees
Best Oceanfront Value in Kihei - Kealia Resort!
Property grounds
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (75)
"We absolutely loved Hana and this location! It was peaceful and calm"
United States
Rebecca Z.
$511 nightly
The price is $598
Jan 13 - Jan 14, 2026
Total with taxes and fees
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Exterior
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
North Kihei
9.6 out of 10, Exceptional, (287)
"Had a great experience here it was close to everything in town and near alot of cool beaches! Would definitely return"
United States
morgan J.
$325 nightly
The price is $380
Jan 5 - Jan 6, 2026
Total with taxes and fees
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
Exterior
Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.0 out of 10, Wonderful, (18)
"Large place with everything you need. Very convenient parking spot, just a few minutes down the road from Paia"
United States
Annette M.
$372 nightly
The price is $374
Dec 21 - Dec 22
Total with taxes and fees
Kuau Surf 2.0 Maui North Shore Locally-Owned
Exterior
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (317)
"great time, great resort, helpful staff"
Canada
Prableen
$573 nightly
The price is $676
Dec 20 - Dec 21
Total with taxes and fees
The Whaler Resort Kaanapali Beach
On the beach
OCEANFRONT RESORT- Winter's here+new rates - Kihei Sands Beachfront Condos-A3

OCEANFRONT RESORT- Winter's here+new rates - Kihei Sands Beachfront Condos-A3

OCEANFRONT RESORT- Winter's here+new rates - Kihei Sands Beachfront Condos-A3
North Kihei
9.8 out of 10, Exceptional, (75)
"Great location. Central to everything. We’ve been here around 20 times and love the little spots like this on the beach. Best sunset ever!!"
United States
Eric F.
$575 nightly
The price is $641
Jan 4 - Jan 5, 2026
Total with taxes and fees
OCEANFRONT RESORT- Winter's here+new rates - Kihei Sands Beachfront Condos-A3
Property grounds
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Central Kihei
9.4 out of 10, Exceptional, (84)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful condo, great views and location"
United States
Pam B.
$499 nightly
The price is $581
Jan 12 - Jan 13, 2026
Total with taxes and fees
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Property grounds
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit
Hana Town Center
9.4 out of 10, Exceptional, (62)
"Everything was perfect!!!! We even had ice cold water waiting on us in the fridge!!! The condo was gorgeous, loved the kitchen! We could see the black sand beach from our gorgeous deck!!! My only regret was not staying longer!!!! I recommend the restaurant in Hana for dinner, it was excellent! We will be back!"
United States
Brenda
$477 nightly
The price is $558
Jan 8 - Jan 9, 2026
Total with taxes and fees
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit
Outdoor dining
Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!

Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!

Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!
Hana Town Center
9.4 out of 10, Exceptional, (62)
"Great stay! Friendly staff and awesome view of the ocean and beach."
United States
Cindy H.
$511 nightly
The price is $598
Jan 8 - Jan 9, 2026
Total with taxes and fees
Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!
On the beach, sun loungers, beach towels
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (11)
"Wonderful place to stay. Awesome host. We had a great time and hopefully be back soon!"
United States
Jennifer D.
$370 nightly
The price is $431
Dec 24 - Dec 25
Total with taxes and fees
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
On the beach
Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot

Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot

Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot
Wailuku
8.6 out of 10, Excellent, (68)
"We had an excellent time! Everything was as advertised. Gorgeous location and very quiet and peaceful. Only downside is that while we were there the building was under construction for a new elevator so there was limited parking and quite a bit of space taken up by the construction "
United States
Dylan R.
$451 nightly
The price is $525
Dec 20 - Dec 21
Total with taxes and fees
Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot
Property grounds
Maui Vista condo, in the heart of Kihei!

Maui Vista condo, in the heart of Kihei!

Maui Vista condo, in the heart of Kihei!
South Kihei
9.6 out of 10, Exceptional, (152)
"Comfortable, clean, short walk to the beach, very quiet, good AC. Third guest slept on an air mattress, small ocean view."
United States
Anonymous traveler
$386 nightly
The price is $452
Jan 9 - Jan 10, 2026
Total with taxes and fees
Maui Vista condo, in the heart of Kihei!
Beach nearby, sun loungers, beach towels
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
South Kihei
10.0 out of 10, Exceptional, (150)
"Cute, cozy, in a great location. Great views from the patio. "
United States
Heidi F.
$372 nightly
The price is $432
Dec 20 - Dec 21
Total with taxes and fees
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
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

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"Close to airport & mall. Nice pedicure place close by and great bakery!"
Bernadine 1-night trip
Posted 23 hours ago
Maui Seaside Hotel

Find out more about Upcountry Maui

Upcountry Maui Condo Rentals information

Number of reviews
2,213
Accommodation
1422 Condo Rentals
Lowest Price
$373
Highest Price
$676

Frequently asked questions

How much do condos in Upcountry Maui cost?
The price range for condos in Upcountry Maui is $373 to $676 per night. No matter your budget, you're sure to find a place that makes your wallet happy — as well as your entire squad! 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.
How many condos are there in Upcountry Maui?
Take your pick of 1422 condos in Upcountry Maui. Whether you're on a trip with the kids or a group of friends, and wherever you're going, Expedia makes it a breeze to find the perfect digs.
Why book your condo in Upcountry Maui with Expedia?
With Expedia, you'll have no trouble finding your dream condo in Upcountry Maui. Looking for a luxury stay? Make the most of our filters to search for properties that are 5-star rated. If you have a fixed budget, select how much you're willing to spend and then browse our amazing deals. We'll help you find the right place whatever your style of travel or plans.
How can I find cheap condos in Upcountry Maui?
A good way to uncover cheap condos in Upcountry Maui is with Expedia's filter tool. Refine your search results by amenities, budget and star rating to take advantage of unbeatable prices in a couple of clicks.

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