Title: Upcountry Maui Vacation Rentals from CA $510: Short-Term Rentals for 2026 | Expedia.ca

[Upcountry Maui Travel Guide](https://expedia.ca/Upcountry-Maui.dx553248621593965869)[Hotels in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Hotels.d553248621593965869.Travel-Guide-Hotels)[Flights to Upcountry Maui](https://expedia.ca/Cheap-Flights-To-Upcountry-Maui.d553248621593965869.Travel-Guide-Flights)[Upcountry Maui Car Rentals](https://expedia.ca/Car-Rentals-In-Upcountry-Maui.d553248621593965869.Car-Rental-Guide)[Upcountry Maui Vacation Packages](https://expedia.ca/Upcountry-Maui.d553248621593965869.Destination-Travel-Guides)

![Haleakala Crater showing landscape views, mountains and tranquil scenes](https://images.trvl-media.com/place/501684/8ed15285-d20f-4fe9-81f0-3e0e3c2f92b8.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Upcountry Maui Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-14&endDate=2025-12-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-15&endDate=2025-12-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Upcountry Maui vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/606a40d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/93574a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/3fdca3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Makawao

[](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information)

10/10

Exceptional

(71)

"What a special property. The location is perfect. We rented it for a work training and it was excellent since everyone has their own room/bathroom but we were able to meet in the large living room for evening presentations/discussions. The host was responsive with questions. It was very clean and check-in was easy. I hope to return again for both this meeting and with family for vacation. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wendy W.

CA $2,197

CA $4,266 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/812b5cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/f3ebbf47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/621c8ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/3bb1e088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Makawao

[](https://www.expedia.ca/Makawao-Hotels-PERMITTED-Charming-LOG-HOUSE-In-REAL-Upcountry-Maui-Magical-And-Peaceful.h18955617.Hotel-Information)

10/10

Exceptional

(50)

"We were a family of nine and this house worked well for us. it has a funky and earthy vibe, which we enjoyed and was a real contrast to Waikiki Beach where we had just stayed. We were there during a warm spell and even though the house did not have air conditioning, the nights were pleasant even if during the day it could get a little warm. Eve, the host, arranged for us to have a private hula lesson, which was a highlight of our stay. We greatly enjoyed the centrality of the location to...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

A Scott W.

CA $1,957

CA $3,652 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Makawao-Hotels-PERMITTED-Charming-LOG-HOUSE-In-REAL-Upcountry-Maui-Magical-And-Peaceful.h18955617.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/02fc15e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/afb5646c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/d096aa40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/41b2cb25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Kula

[](https://www.expedia.ca/Kula-Hotels-Eco-Friendly-Modern-Home.h23268927.Hotel-Information)

10/10

Exceptional

(185)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Peter A.

CA $911

CA $1,814 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Kula-Hotels-Eco-Friendly-Modern-Home.h23268927.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/3930425c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/e0e2bd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/98fa11d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/bd3af031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Haiku

[](https://www.expedia.ca/Haiku-Hale-3-Bedroom-Maui-Getaway.h97567999.Hotel-Information)

10/10

Exceptional

(4)

"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda S.

CA $923

CA $1,664 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Haiku-Hale-3-Bedroom-Maui-Getaway.h97567999.Hotel-Information)

![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/51ee3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/a42f39cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/f7f2f5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/25e08687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hana Town Center

[](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information)

9.6/10

Exceptional

(409)

"Cute place with character in Hana. It was so nice to not rush the road to Hana and stay in this remote location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Annette M.

CA $269

CA $548 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/606af9b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/eeb50dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/7c06baf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32490000/32484100/32484007/be9ac5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Hana Town Center

[](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information)

9.6/10

Exceptional

(191)

"Super lovely place, I wish we were staying longer! Has everything you need. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicole

CA $284

CA $640 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Hana-Hotels-Beautiful-Cottage-In-The-Heart-Of-Hana.h32484007.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119810000/119804800/119804724/5d185f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/120000000/119810000/119804800/119804724/0d333320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![55-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/120000000/119810000/119804800/119804724/88e4e20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, memory foam beds](https://images.trvl-media.com/lodging/120000000/119810000/119804800/119804724/be0e51c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo resort in South Kihei

[](https://www.expedia.ca/Kihei-Hotels-Signature-Residences-At-Maui-Banyan.h119804724.Hotel-Information)

10/10

Exceptional

(4)

"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melinda

CA $129

CA $842 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Kihei-Hotels-Signature-Residences-At-Maui-Banyan.h119804724.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87740000/87738000/87737984/2f558c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/88000000/87740000/87738000/87737984/21fae2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87740000/87738000/87737984/edb0f3d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87740000/87738000/87737984/2612e5af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hana Town Center

[](https://www.expedia.ca/Hana-Hotels-Stay-In-Hana-2.h87737984.Hotel-Information)

9.6/10

Exceptional

(45)

"Staying here was a pleasure - from the ease of the check in process, to the cleanliness of the room, amenities and location, we're so glad we chose this home!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenny E.

CA $259

CA $479 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Hana-Hotels-Stay-In-Hana-2.h87737984.Hotel-Information)

![Beach towels](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/0b16ee80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/ed259162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/739cc806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/bb7cfb8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Kuau

[](https://www.expedia.ca/Paia-Hotels-AC-North-Shore-Maui-PaiaKuau-BrJust-Steps-Away-To-Mamas-And-Beach.h19651188.Hotel-Information)

9.4/10

Exceptional

(196)

"Very quiet safe place. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Monica

CA $255

CA $606 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Paia-Hotels-AC-North-Shore-Maui-PaiaKuau-BrJust-Steps-Away-To-Mamas-And-Beach.h19651188.Hotel-Information)

![4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/cc604c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/0edd56a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 3 Bedrooms, Ocean View | Balcony view](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/8aca803a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/7880dbd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo resort in Lahaina

[](https://www.expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.Hotel-Information)

8.8/10

Excellent

(2881)

"Wonderful stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Quiauna

CA $395

CA $1,102 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/7f8f329c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/0aa72530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/w2000h1163x0y0-8d5e7871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482970/c892d567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Hana Town Center

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Oceanview-Kauiki-Corner-Amazing-View.h33482970.Hotel-Information)

9.6/10

Exceptional

(76)

"Nice easy check in. Easy access to black sand beach (not the State Park)."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brett

CA $446

CA $635 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Oceanview-Kauiki-Corner-Amazing-View.h33482970.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/5fd97c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/2e690804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/6a813fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/0e7693c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kaʻeleku

[](https://www.expedia.ca/Hana-Hotels-Secluded-Cottage-On-Tropical-Flower-Farm.h33498605.Hotel-Information)

9.4/10

Exceptional

(281)

"This was a great location, comfortable cute little cottage."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Briana B.

CA $406

CA $767 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Hana-Hotels-Secluded-Cottage-On-Tropical-Flower-Farm.h33498605.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/9bf9b442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/0a266b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/w851h563x0y1-545b8881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/376222a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Hana

[](https://www.expedia.ca/Hana-Hotels-Tropical-Romance-Lush-Gardens-In-Heavenly-Hana.h33506788.Hotel-Information)

10/10

Exceptional

(90)

"Very unique property near Hana. Great experience!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Keith R.

CA $427

CA $747 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Hana-Hotels-Tropical-Romance-Lush-Gardens-In-Heavenly-Hana.h33506788.Hotel-Information)

![Sundeck](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/5ccd0b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beachfront Two Bedrooms | Living area](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/1ac7478b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Studio, Kitchenette, Garden/Poolside View (No Ocean View) | Private kitchen](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/de817031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/8474cfac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Lahaina

[](https://www.expedia.ca/Lahaina-Hotels-Napili-Sunset-On-The-Beach.h117871.Hotel-Information)

9.2/10

Wonderful

(647)

"Location was excellent"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Polly

CA $387

CA $457 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Lahaina-Hotels-Napili-Sunset-On-The-Beach.h117871.Hotel-Information)

![Beach nearby, white sand, beach towels](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/77cc11a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Studio, Garden View | Living area](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/34a4b10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, Partial Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/e0be1c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/a901f03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Lahaina

[](https://www.expedia.ca/Kapalua-Hotels-Napili-Village-Hotel.h103028003.Hotel-Information)

9.0/10

Wonderful

(142)

"Exactly what we were looking for! Close walking distance to beach and dining!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tessa

CA $304

CA $359 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Kapalua-Hotels-Napili-Village-Hotel.h103028003.Hotel-Information)

![Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/abca45f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/6918496a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Ocean View | Private kitchenette](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/48af28ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/78a25dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in South Kihei

[](https://www.expedia.ca/Kihei-Hotels-Aston-Maui-Hill.h24554.Hotel-Information)

9.0/10

Wonderful

(852)

"Clean room, attentive staff, and tons of things for kids and adults alike to do! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Misty

CA $522

CA $616 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Kihei-Hotels-Aston-Maui-Hill.h24554.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/w1170h877x0y5-51fd63d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/96d0f8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/af4b8884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/8b711bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in North Kihei

[](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18980054.Hotel-Information)

10/10

Exceptional

(266)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Noah C.

CA $123

CA $524 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18980054.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34190000/34188200/34188116/6e8952cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34190000/34188200/34188116/fb842c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34190000/34188200/34188116/47225e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/35000000/34190000/34188200/34188116/541699b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Hana Town Center

[](https://www.expedia.ca/Hana-Hotels-Oceanview-103-At-Hana-Kai-Maui-1-Bedroom.h34188116.Hotel-Information)

9.6/10

Exceptional

(111)

"Everything Good "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marc

CA $523

CA $740 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Hana-Hotels-Oceanview-103-At-Hana-Kai-Maui-1-Bedroom.h34188116.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71600000/71595200/71595183/b6438d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/72000000/71600000/71595200/71595183/w9528h2266x0y0-3f0b5a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71600000/71595200/71595183/fe7989e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71600000/71595200/71595183/5dbccaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hana Town Center

[](https://www.expedia.ca/Hana-Hotels-Oceanview-Condo-In-Hana-Let-The-Ocean-Lull-You-To-Sleep.h71595183.Hotel-Information)

9.2/10

Wonderful

(115)

"A good place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Xiaohong

CA $344

CA $634 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Hana-Hotels-Oceanview-Condo-In-Hana-Let-The-Ocean-Lull-You-To-Sleep.h71595183.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/b85a7c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/747fb065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, Multiple Beds, Oceanfront (2 Baths) | Living area](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/2f70d75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, Ocean View | Living area](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/c047658e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Lahaina

[](https://www.expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.Hotel-Information)

9.6/10

Exceptional

(315)

"great time, great resort, helpful staff"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Prableen

CA $337

CA $898 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.Hotel-Information)

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

![Wailea Beach Resort - Marriott, Maui](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/b323b293_y.jpg)

### Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"It was a great place to stay with my family for my 4-year-old twin's birthday, and there were a lot of activities to do such as yoga, pilates, kids activities, and among all other things. Not to mention the road trip that we’ve taken to Hana, which was very nice and fun."

[](https://expedia.ca/Kihei-Hotels-Wailea-Beach-Resort-Marriott.h20303.Hotel-Information)

![Maui Coast Hotel](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/ffbd6b5d_y.jpg)

### Maui Coast Hotel

10/10 Excellent

"Honestly, one of the best hotel stays I’ve ever had! The amenities and service for the price point were outstanding. Every service member we encountered was helpful, kind, enthusiastic, and helpful. The staff was always very accommodating, the room was clean and spacious, and the view from the pool was great. Wonderful location, both in Kihei and also on the island as you have easy access to the north, east or west of the island. The hotel is directly across the street from the beach and has two grocery stores within walking distance. I would 100% recommend this hotel and will definitely stay again if I return."

[](https://expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.Hotel-Information)

![Maui Seaside Hotel](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg)

### Maui Seaside Hotel

10/10 Excellent

"The staff was very friendly and always ready to check your needs."

[](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information)

![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg)

### Fairmont Kea Lani Maui

10/10 Excellent

"Friendly staff, good restaurant"

[](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information)

![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg)

### Royal Lahaina Resort & Bungalows

10/10 Excellent

"Clean room, friendly staff, amenities were great. We loved the bars & the beauty of the property "

[](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information)

![Sheraton Maui Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/22900/22894/w4000h2664x0y0-b7d636ba_y.jpg)

### Sheraton Maui Resort & Spa

10/10 Excellent

"Not too busy. Excellent and we will return. Walkable superb snorkeling at black rock "

[](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information)

![The Whaler Resort Kaanapali Beach](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/b85a7c13_y.jpg)

### The Whaler Resort Kaanapali Beach

10/10 Excellent

"We had an amazing condo on the 9th floor that had a huge lanai and was oceanfront. Lots of whales, beautiful sunset and the moon was great at night too. We had a wonderful stay . "

[](https://expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.Hotel-Information)

![OUTRIGGER Kaanapali Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/11600/11554/82021c2d_y.jpg)

### OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"Everything was phenomenal!"

[](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information)

![Gods Peace Of Maui](https://images.trvl-media.com/lodging/114000000/113840000/113837400/113837325/51cf4e1f_y.jpg)

### Gods Peace Of Maui

10/10 Excellent

"Loved the hibiscus eoom"

[](https://expedia.ca/Makawao-Hotels-Gods-Peace-Of-Maui.h113837325.Hotel-Information)

## Find out more about Upcountry Maui

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upcountry Maui. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

## Explore a world of travel with Expedia

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