Title: Upcountry Maui Vacation Rentals from CA $513: 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)

![View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds.
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![](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-05-22&endDate=2026-05-24&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)

![Interior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/3fdca3f0.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)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/d58312bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

Makawao

10/10

Exceptional

(73 reviews)

"We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! "

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

Kari L.

CA $2,152

CA $4,308 total

includes taxes & fees

Feb 23 - Feb 24

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/7f0e124d.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)

### Haiku Hale - 3 Bedroom Maui Getaway!

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

Haiku

10/10

Exceptional

(4 reviews)

"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 $545

CA $1,179 total

includes taxes & fees

Feb 3 - Feb 4

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

![Premier Suite, 3 Bedrooms, Balcony, Ocean View (Konea 701, 3Bath) | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/639e276d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite, 3 Bedrooms (Piilani) | Living area](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/c0a57d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/0d8c016f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### OUTRIGGER Honua Kai Resort & Spa

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

Lahaina

8.8/10

Excellent

(2,909 reviews)

"Great place nice people very clean and great food"

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

Dalen L

CA $431

CA $1,134 total

includes taxes & fees

Feb 2 - Feb 3

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

![2 outdoor pools](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/4464a924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/e5fc0ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (1 Bedroom,  Ocean View) | Living area](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/aa9726a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite (1 Bedroom Ocean View) | Living area](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/64d5d800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aston Maui Kaanapali Villas

[](https://www.expedia.ca/Lahaina-Hotels-Aston-Maui-Kaanapali-Villas.h18735.Hotel-Information)

Lahaina

8.8/10

Excellent

(2,540 reviews)

"Nice clean room, nice staff and very quiet. "

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

Marjie

CA $513

CA $729 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Lahaina-Hotels-Aston-Maui-Kaanapali-Villas.h18735.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/6b7c1eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/d8badfdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/0cb24ea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/44c7a72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Westin Nanea Ocean Villas, Ka'anapali

[](https://www.expedia.ca/Lahaina-Hotels-The-Westin-Nanea-Ocean-Villas.h16700689.Hotel-Information)

Lahaina

9.4/10

Exceptional

(482 reviews)

"Wonderful place to stay. "

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

Sharon Lynn

CA $841

CA $998 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Lahaina-Hotels-The-Westin-Nanea-Ocean-Villas.h16700689.Hotel-Information)

![Beachfront Two Bedrooms](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/ed3402a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beachfront Two Bedrooms](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/51b85b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 Bedroom Beach Apartment | Living room](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/a7bae0d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/120000/117900/117871/28698dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Napili Sunset on the Beach

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

Lahaina

9.2/10

Wonderful

(648 reviews)

"Great Hotel! Super clean! Has everything you need for perfect vacation!"

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

Sergii

CA $379

CA $450 total

includes taxes & fees

Jan 31 - Feb 1

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

![Classic Condo, 1 Bedroom, Lanai, Ocean View | View from room](https://images.trvl-media.com/lodging/120000000/119660000/119657400/119657382/b15b6dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/120000000/119660000/119657400/119657382/bef7c42a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Condo, 1 Bedroom, Lanai, Ocean View | Living area](https://images.trvl-media.com/lodging/120000000/119660000/119657400/119657382/86b16f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/120000000/119660000/119657400/119657382/ef51edad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kuleana Club - 513

[](https://www.expedia.ca/Kahana-Hotels-Kuleana-Club-513.h119657382.Hotel-Information)

Lahaina

10/10

Exceptional

(1 review)

"Clean room, easy check in process, great property with great pool and little beach area to see turtles. We were on the third floor and had to carry all our suitcases up the flights of stairs but being able to see the whales off the Lanai every morning was worth it "

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

Andrea

[](https://www.expedia.ca/Kahana-Hotels-Kuleana-Club-513.h119657382.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/850ae64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 Bedroom Aloha Suite | View from room](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/076e228c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lanai](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/2adf348d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aston Kaanapali Shores

[](https://www.expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information)

Lahaina

8.8/10

Excellent

(3,977 reviews)

"Our room was great and the staff were always so friendly. Perfect place to stay for a good value. "

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

Emily

CA $417

CA $535 total

includes taxes & fees

Jan 31 - Feb 1

[](https://www.expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.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 Apartment, Partial Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/c9719f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Studio, Partial Ocean View | Beach/ocean view](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/559abe53.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)

### Napili Village Hotel

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

Lahaina

9.0/10

Wonderful

(156 reviews)

"Beautiful hotel although not on the beach. Nice garden with pool when ocean was rough."

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

Robert

CA $311

CA $370 total

includes taxes & fees

Feb 4 - Feb 5

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

![Suite, Multiple Beds, Garden View (2 Baths) | Garden view](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/3dafba07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/bbe9db3a.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)

### The Whaler Resort Kaanapali Beach

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

Lahaina

9.6/10

Exceptional

(345 reviews)

"We loved the location. Very clean & the staff was very nice "

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

Pamela

CA $422

CA $995 total

includes taxes & fees

Jan 31 - Feb 1

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/970b5e33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/e37012bd.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)

### Fisher's Hana Bay Hale, Across from Hana Bay

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

Hana Town Center

9.6/10

Exceptional

(416 reviews)

"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"

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

Nicholas

CA $263

CA $541 total

includes taxes & fees

Feb 16 - Feb 17

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

![Property grounds](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/89d58844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/w1242h1242x0y483-55e80f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/8816e3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/29f223cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

[](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.Hotel-Information)

Kaʻeleku

9.8/10

Exceptional

(79 reviews)

"Phenomenal property for your stay in Hana - especially for a large group "

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

Logan G.

CA $777

CA $1,399 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/222e71f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/4cd51c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/e6b6d1ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/7ca51a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Napili Shores Maui by OUTRIGGER

[](https://www.expedia.ca/Lahaina-Hotels-Napili-Shores-Maui-By-Outrigger.h27045.Hotel-Information)

Lahaina

9.0/10

Wonderful

(1,744 reviews)

"Beautiful location, nice, clean rooms, friendly staff, and eating facilities on site!"

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

Larry Henry

CA $432

CA $513 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Lahaina-Hotels-Napili-Shores-Maui-By-Outrigger.h27045.Hotel-Information)

![Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/bc2b4da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Ocean View | Living area](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/02b478dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Tennis court](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/1a64b291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/a32a9683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aston Maui Hill

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

South Kihei

9.0/10

Wonderful

(873 reviews)

"The location was great, staff provided clean towels and bedding daily. "

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

Christine

CA $660

CA $783 total

includes taxes & fees

Feb 25 - Feb 26

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

![Pool](https://images.trvl-media.com/lodging/34000000/33490000/33484900/33484858/595ad562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33484900/33484858/8d4265cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33484900/33484858/11aed1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33490000/33484900/33484858/d655db7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

[](https://www.expedia.ca/Hana-Hotels-MINUTES-TO-HAMOA-BEACH.h33484858.Hotel-Information)

Hana

10/10

Exceptional

(251 reviews)

"We loved staying here! It had all the amenities, was so comfortable and very easy for check in and check out. Perfect place for a quiet and relaxing stay in Hana. Also, SO close to the most gorgeous beach, only a two minute drive!"

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

Kristi O.

CA $472

CA $811 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Hana-Hotels-MINUTES-TO-HAMOA-BEACH.h33484858.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34160000/34152900/34152879/911c08bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/35000000/34160000/34152900/34152879/e9c5da82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34160000/34152900/34152879/6ae6f44c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/35000000/34160000/34152900/34152879/245620e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Oceanview-Waiohinu-Upper-Floor-Amazing-View-Decor.h34152879.Hotel-Information)

Hana Town Center

9.6/10

Exceptional

(76 reviews)

"Amazing cozy space, beautiful view and everything needed for two! "

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

Jamie

CA $517

CA $736 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Oceanview-Waiohinu-Upper-Floor-Amazing-View-Decor.h34152879.Hotel-Information)

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

![On the beach, beach towels](https://images.trvl-media.com/lodging/35000000/34190000/34188200/34188116/4da4b07a.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)

![Exterior](https://images.trvl-media.com/lodging/35000000/34190000/34188200/34188116/523106bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Hana Town Center

9.6/10

Exceptional

(112 reviews)

"Everything Good "

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

Marc

CA $517

CA $736 total

includes taxes & fees

Feb 2 - Feb 3

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

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27130000/27128500/27128470/db1a52c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27130000/27128500/27128470/e780d0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27128500/27128470/f33bd462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/28000000/27130000/27128500/27128470/1c309c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing home away from home- honeymoon friendly

[](https://www.expedia.ca/Hana-Hotels-Relaxing-Home-Away-From-Home.h27128470.Hotel-Information)

Hana

10/10

Exceptional

(282 reviews)

"Lovely property with enormous views. Very quiet and relaxing. "

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

caren w.

CA $379

CA $724 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Hana-Hotels-Relaxing-Home-Away-From-Home.h27128470.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330791/7b6d62ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330791/64a2bcd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330791/9c194cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330791/bbeec08e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

[](https://www.expedia.ca/Hana-Hotels-IDEAL-BEACH-LOCATION-2-BR-LARGE-DECK-PRIVATE.h34330791.Hotel-Information)

Hana

10/10

Exceptional

(189 reviews)

"Beautiful peaceful home. "

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

Rebecca

CA $472

CA $811 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Hana-Hotels-IDEAL-BEACH-LOCATION-2-BR-LARGE-DECK-PRIVATE.h34330791.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/6dac1305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/3e86f405.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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33506800/33506788/w850h563x1y1-debd2996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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

Hana

10/10

Exceptional

(92 reviews)

"Very unique property near Hana. Great experience!"

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

Keith R.

CA $440

CA $767 total

includes taxes & fees

Jan 31 - Feb 1

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&regionId=553248621593965869&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cottages

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Aparthotels

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Condos

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Apartments

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Private vacation homes

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America&regionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-04-30&d1=2026-04-30&endDate=2026-05-03&d2=2026-05-03&lodging=VILLA)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Upcountry+Maui%2C+Hawaii%2C+United+States+of+America&regionId=553248621593965869&latLong=20.754365%2C-156.241192&adults=2&startDate=2026-04-30&d1=2026-04-30&endDate=2026-05-03&d2=2026-05-03&lodging=CABIN)

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## Top Upcountry Maui Hotel Reviews

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

### Maui Seaside Hotel

10/10 Excellent

"Really clean rooms and friendly staff. The restaurant next door was amazing as well, definitely will stay here again. "

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

"Perfect stay in Maui at Kaanapali beach. Very friendly people work in the hotel and you really be in your home out from your home. Nice resort to spend your holidays with a relaxing time. Overall excellent. Wish to return shortly!!!"

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

![Four Seasons Resort Maui at Wailea](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg)

### Four Seasons Resort Maui at Wailea

10/10 Excellent

"The Four Seasons Wailea was, once again, exceptional. All the staff, from the front desk to the pool to the outrigger crew to housekeeping, all helped make our stay one we will never forget. We were sad to leave and hope to return soon!"

[](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.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

"Good staff, good food, good location "

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

![Aston Kaanapali Shores](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615_y.jpg)

### Aston Kaanapali Shores

10/10 Excellent

"Great room with views and staff is always amazing "

[](https://expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information)

![Grand Wailea Maui, A Waldorf Astoria Resort](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg)

### Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent

"The entire staff is soooo kind! Absolutely beautiful grounds and rooms. We ate at all the restaurants there. While pricey, everything was delicious. Pools are very fun, including the pool bar. And, very easy beach access."

[](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information)

![Maui Beach Hotel](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg)

### Maui Beach Hotel

10/10 Excellent

"Everything was good. Best location close to airport. Friendly staff."

[](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information)

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

### Maui Coast Hotel

10/10 Excellent

"this was our first stay at maui coast hotel and will not be our last. staff was awesome. live music poolside every night was amazing."

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

"Beautiful property "

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

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- [Hotels in Hawaii Island](https://expedia.ca/Hawaii-Island-Hotels.d180074.Travel-Guide-Hotels)
- [All Inclusive Resorts and Hotels in Oahu](https://expedia.ca/Oahu-Hotels-All-Inclusive-Hotel.0-0-d180077-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Maui](https://expedia.ca/Maui-Hotels-Cheap-Hotels.0-0-d180073-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Maui](https://expedia.ca/Maui-Hotels-Oceanfront-Hotels.0-0-d180073-tOceanfrontHotels.Travel-Guide-Filter-Hotels)

Flights

- [Flights to Maui](https://expedia.ca/Cheap-Flights-To-Maui.d180073.Travel-Guide-Flights)
- [Flights to Oahu](https://expedia.ca/Cheap-Flights-To-Oahu.d180077.Travel-Guide-Flights)
- [Flights to Hawaii Island](https://expedia.ca/Cheap-Flights-To-Hawaii-Island.d180074.Travel-Guide-Flights)
- [Flights to Kauai](https://expedia.ca/Cheap-Flights-To-Kauai.d180075.Travel-Guide-Flights)

Cars

- [Car rentals in Kauai](https://expedia.ca/Car-Rentals-In-Kauai.d180075.Car-Rental-Guide)
- [Car rentals in Oahu](https://expedia.ca/Car-Rentals-In-Oahu.d180077.Car-Rental-Guide)
- [Car rentals in Maui](https://expedia.ca/Car-Rentals-In-Maui.d180073.Car-Rental-Guide)

Activities

- [Things to do in Oahu](https://expedia.ca/Things-To-Do-In-Oahu.d180077.Travel-Guide-Activities)
- [Things to do in Kauai](https://expedia.ca/Things-To-Do-In-Kauai.d180075.Travel-Guide-Activities)
- [Things to do in Maui](https://expedia.ca/Things-To-Do-In-Maui.d180073.Travel-Guide-Activities)

Packages

- [Maui All-inclusive Vacation Packages](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations/180073/Maui)
- [Oahu Vacations](https://expedia.ca/Oahu.d180077.Destination-Travel-Guides)
- [Hawaii Island Vacations](https://expedia.ca/Hawaii-Island.d180074.Destination-Travel-Guides)
- [Kauai Vacations](https://expedia.ca/Kauai.d180075.Destination-Travel-Guides)
- [Maui Vacations](https://expedia.ca/Maui.d180073.Destination-Travel-Guides)

Vacation Rentals

- [North Shore Vacation Rentals](https://expedia.ca/North-Shore-Vacation-Rentals.d6048743.Travel-Guide-VacationRentals)
- [Kauai Vacation Rentals](https://expedia.ca/Kauai-Vacation-Rentals.d180075.Travel-Guide-VacationRentals)
- [Oahu Vacation Rentals](https://expedia.ca/Oahu-Vacation-Rentals.d180077.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals](https://expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)

General

- [Visit Hawaii Island](https://expedia.ca/Hawaii-Island.dx180074)

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