Title: Upcountry Maui Vacation Rentals from CA $275: Short-Term Rentals for 2025 | Expedia.ca

  

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# Upcountry Maui Vacation Rentals

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## Check prices for these dates

Tonight

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-29&endDate=2025-10-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-30&endDate=2025-10-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Upcountry Maui

![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.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)

![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.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)

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

Makawao

10/10

Exceptional

(70)

"This property was indescribable! Our stay was amazing and the host was so very accommodating! Check-in was a breeze and every room was meticulously cleaned, arranged, and ready for our group. "

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

James B.

CA $2,224

CA $4,428 total

includes taxes & fees

Nov 17 - Nov 18

[](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/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)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23270000/23269000/23268927/29bbe892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Kula

10/10

Exceptional

(181)

"Great stay"

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

Peter A.

CA $797

CA $1,615 total

includes taxes & fees

Nov 5 - Nov 6

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/1ceb2db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/1bd600e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/bf8d9964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/ff665104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku

CA $640

CA $1,666 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Haiku-Hotels-2-Mi-To-Hana-Hwy-Haiku-Home-W-Ocean-Views.h115732203.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)

![Interior](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/bd3af031.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)

### Haiku Hale - 3 Bedroom Maui Getaway!

Haiku

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 $689

CA $1,363 total

includes taxes & fees

Oct 31 - Nov 1

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

![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)

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

### Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Hana

9.6/10

Exceptional

(189)

"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 $237

CA $578 total

includes taxes & fees

Oct 31 - Nov 1

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

![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)

![Balcony view](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/0edd56a9.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)

### OUTRIGGER Honua Kai Resort & Spa

Lahaina

8.8/10

Excellent

(2856)

"Resort was beautiful and family friendly. Definitely will stay here again with the rest of the family"

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

Alisha

CA $407

CA $1,120 total

includes taxes & fees

Nov 22 - Nov 23

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

![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/530ff241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/c11638c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/70f3f0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/2f01dccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Hana

9.6/10

Exceptional

(403)

"We enjoyed our Stay, especially the near zu the entrance of the Volcano NP was really great."

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

Katja Monika B.

CA $243

CA $497 total

includes taxes & fees

Nov 8 - Nov 9

[](https://www.expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.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)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/58ae806d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Kahului

9.6/10

Exceptional

(407)

"Wonderful property and a great place to stay in Hana"

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

Daniel

CA $272

CA $556 total

includes taxes & fees

Oct 31 - Nov 1

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

![Garden](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/ced36266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/f9c6c56b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Apartment, Garden View (Haiku #2)](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/4e5368b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Apartment, Garden View (Haiku #2) | Living area](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/6bb7cdbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yonegan Maui Getaways - Haiku

Haiku

9.0/10

Wonderful

(7)

"Loved having the hot tub to come home to!!"

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

Pedro

CA $171

CA $340 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Haiku-Hotels-Yonegan-Maui-Getaways-Haiku.h117919946.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)

![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)

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

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

Hana

9.6/10

Exceptional

(109)

"Location and view were beautiful. The veranda area was lovely for eating al fresco."

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

G William F.

CA $420

CA $598 total

includes taxes & fees

Oct 31 - Nov 1

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

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

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

Hana

10/10

Exceptional

(88)

"Most beautiful setting. Everything was wonderful "

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

renee s.

CA $432

CA $752 total

includes taxes & fees

Oct 31 - Nov 1

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

![Exterior](https://images.trvl-media.com/lodging/72000000/71600000/71595200/71595183/c4782a88.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)

![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)

### Oceanview Condo in Hana-Let the ocean lull you to sleep

Hana

9.2/10

Wonderful

(109)

"A good place to stay "

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

Xiaohong

CA $279

CA $550 total

includes taxes & fees

Oct 31 - Nov 1

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

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27130000/27128500/27128470/9dd7f651.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27128500/27128470/5be8bd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing home away from home- honeymoon friendly

Hana

10/10

Exceptional

(280)

"Silence and great location just in front of the ocean."

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

Michele L.

CA $370

CA $709 total

includes taxes & fees

Nov 18 - Nov 19

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

![Property grounds](https://images.trvl-media.com/lodging/35000000/34200000/34192200/34192134/9820a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34200000/34192200/34192134/b135f64c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34200000/34192200/34192134/756c7238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34200000/34192200/34192134/616b81f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hana

9.4/10

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

Brenda

CA $396

CA $567 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Hana-Hotels-Hana-Kai-Maui-Partial-Oceanview-Kama-Lower-Corner.h34192134.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)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19660000/19651200/19651188/0b46b2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Kuau

9.4/10

Exceptional

(194)

"6 day stay.Good location, quite and relaxing.Paia close by for most of ones needs"

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

Edward G.

CA $258

CA $614 total

includes taxes & fees

Oct 31 - Nov 1

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

![Exterior](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/w5464h3630x0y5-53069acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/732f839b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/4021aaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/231f7809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Royal Lahaina Bungalows & Spa

Lahaina

CA $389

CA $533 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Lahaina-Hotels-Royal-Lahaina-Bungalows-Spa.h115794140.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/6389d34f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/77cc46dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite (1 Bedroom Ocean View)](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/59889d7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/0d5ab47f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aston Maui Kaanapali Villas

Lahaina

8.8/10

Excellent

(2483)

"Must stay walkable to beach , beachfront cafe"

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

brittany

CA $339

CA $523 total

includes taxes & fees

Nov 7 - Nov 8

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

![Property grounds](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/95afb621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/w1242h1656x0y276-798b978b.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/fff4e05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hana

9.8/10

Exceptional

(76)

"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 $640

CA $1,207 total

includes taxes & fees

Oct 31 - Nov 1

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498605/4807a545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded cottage on Tropical flower farm

Hana

9.4/10

Exceptional

(274)

"A wonderful place. Highly recomend"

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

Alex s.

CA $411

CA $779 total

includes taxes & fees

Nov 11 - Nov 12

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

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/963f0910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/007570d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, DVD player, books](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/bd738079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/71d86e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Hana

9.8/10

Exceptional

(232)

"Wonderful location!"

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

Christopher M W.

CA $408

CA $863 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.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=2025-11-13&endDate=2025-11-14&regionId=553248621593965869&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Upcountry Maui Hotel Reviews

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

### Maui Coast Hotel

10/10 Excellent

"The hotel staff was wonderful, the room was clean, happy hour specials were great and a very nice pool and breakfast!"

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

![Hilton Vacation Club Ka'anapali Beach Maui](//images.trvl-media.com/lodging/1000000/30000/23100/23042/7a9e8592_y.jpg)

### Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent

"Staff great, clean room. We didn’t eat at the hotel "

[](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.Hotel-Information)

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

### Aston Kaanapali Shores

10/10 Excellent

"Great stay and fun activities in the area"

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

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

### Sheraton Maui Resort & Spa

10/10 Excellent

"Clean"

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

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

### OUTRIGGER Kaanapali Beach Resort

10/10 Excellent

"Overall a great experience. Close to everything on the west side. Many shopping and dining options within a short walk. Exceptional staff!"

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

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

### Maui Seaside Hotel

10/10 Excellent

"Room was a little out dated but it was well worth the convenience. Staff was really nice and helpful and Parking was a little frustrating "

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

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

### Fairmont Kea Lani Maui

10/10 Excellent

"Amazing. Our favourite hot on the planet! "

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

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

### Royal Lahaina Resort & Bungalows

10/10 Excellent

"Rooms were very clean. Housekeeping made sure we enjoyed our vacation. "

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

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

### Four Seasons Resort Maui at Wailea

10/10 Excellent

"Offered turn down service; the staff went above any beyond to ensure that we were comfortable. "

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

## Find out more about Upcountry Maui

**Everything you need to know about** **Upcountry Maui** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upcountry Maui vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Upcountry Maui vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Upcountry Maui. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upcountry Maui vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upcountry Maui vacation rentals we have selected for you start as low as CA $275 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Upcountry Maui rentals**

At Expedia, we put the best Upcountry Maui vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upcountry Maui rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upcountry Maui vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upcountry Maui. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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-   [Condo Rentals in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Condos.d553248621593965869-aaCondos.Travel-Guide-Accommodation)
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General

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

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)