Title: Upcountry Maui Vacation Home Rentals from CA $359: Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Vacation-Rentals.d553248621593965869.Travel-Guide-VacationRentals)[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. #AboveItAll](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Project Forever # Upcountry Maui Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [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) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Our top choices for Upcountry Maui vacation homes ![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) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/7fed233a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/a95cda94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18955700/18955617/c43912da.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) "Eve and her family were incredibly kind and welcoming. The property was better than we hoped with ample space for the kids to explore. We loved our stay and would come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica S. CA $1,957 CA $3,493 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) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.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) ![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) ### 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 $2,196 CA $4,365 total includes taxes & fees Jan 6 - Jan 7, 2026 [](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) ![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) ### 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 17 - Dec 18 [](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) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/f7f2f5f8.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/c16d15e2.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 $550 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information) ![Studio, Garden View (Haiku #6) | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/c916924e_edited_d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/118000000/117920000/117920000/117919946/5dd9fc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Garden View (Haiku #3)](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/7e83a53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Haiku [](https://www.expedia.ca/Haiku-Hotels-Yonegan-Maui-Getaways-Haiku.h117919946.Hotel-Information) 9.0/10 Wonderful (12) "Loved having the hot tub to come home to!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pedro CA $189 CA $359 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Haiku-Hotels-Yonegan-Maui-Getaways-Haiku.h117919946.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/167b0628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/00107baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/da2f3e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/8c976e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hana Town Center [](https://www.expedia.ca/Hana-Hotels-Beautiful-Home-In-The-Heart-Of-Hana.h32488569.Hotel-Information) 9.4/10 Exceptional (146) "Great space. Centrally located with easy proximity to food & groceries. Perfect for our needs. Comfy bed too. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy A. CA $309 CA $695 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Home-In-The-Heart-Of-Hana.h32488569.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/2f8ffeb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/d6318fc3.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/20000000/19670000/19667500/19667488/cfa3cd75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/66e90678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in North Kihei [](https://www.expedia.ca/Kihei-Hotels-Tropical-Honeymoon-Suite-BBQ.h19667488.Hotel-Information) 9.8/10 Exceptional (109) "This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Troy s. CA $186 CA $742 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Kihei-Hotels-Tropical-Honeymoon-Suite-BBQ.h19667488.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) ![Smart TV, stereo](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/b05506bf.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) ### Vacation Home in Kaʻeleku [](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.Hotel-Information) 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 $744 CA $1,337 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/e245fd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/963f0910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/fae2554b.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/f338844a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kaʻeleku [](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.Hotel-Information) 9.8/10 Exceptional (235) "Great property and excellent location with a perfect balance between privacy and proximity to Hana. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael T. CA $482 CA $955 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666330/20157a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666330/737e97bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666330/ed9d33cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666330/8547875d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Wailuku [](https://www.expedia.ca/Wailuku-Hotels-The-Ulu-Suite-Timeless-Elegance-Free-Breakfast.h102666330.Hotel-Information) 10/10 Exceptional (4) "Parking and check in was easy and just as described. The interior was simple, yet felt upscale. Lovely original art on the walls, comforts bed, and bathroom and shower were wonderful. Would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) e o. CA $489 CA $643 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Wailuku-Hotels-The-Ulu-Suite-Timeless-Elegance-Free-Breakfast.h102666330.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666310/20317467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666310/ad56d39e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666310/60c3f99b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102670000/102666400/102666310/a67a2cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Wailuku [](https://www.expedia.ca/Wailuku-Hotels-Hinano-Suite-Vintage-Relaxation.h102666310.Hotel-Information) 10/10 Exceptional (3) "Thank you for a wonderful stay. Our suite was great and comfortable. We well truly be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JoAnn H. CA $506 CA $664 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Wailuku-Hotels-Hinano-Suite-Vintage-Relaxation.h102666310.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/b61b319f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/8aeb2dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/842daabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, blackout drapes, iron/ironing board, internet](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/933ce1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lahaina [](https://www.expedia.ca/Lahaina-Hotels-New-The-Aloha-Cottage-In-Puamana.h18993062.Hotel-Information) 9.8/10 Exceptional (86) "Cottage was clean and well kept. Location is convenient to shopping, dining, and many beaches including a small beach just a short walk from the property. Stay was very enjoyable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert B. CA $365 CA $1,204 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Lahaina-Hotels-New-The-Aloha-Cottage-In-Puamana.h18993062.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/846341ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/b66db40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/8a98a8ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/1515fb96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hana Town Center [](https://www.expedia.ca/Hana-Hotels-Hana-Homestead-By-The-Beach.h32643004.Hotel-Information) 9.8/10 Exceptional (137) "This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $830 CA $1,931 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hana-Hotels-Hana-Homestead-By-The-Beach.h32643004.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/4212c7da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/w327h250x0y0-14e4896d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/96a01773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/8ea86854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lahaina [](https://www.expedia.ca/Lahaina-Hotels-Oceanview-Retreat-In-Puamana-Steps-From-The-Beach-Surf.h114567607.Hotel-Information) 10/10 Exceptional (2) CA $463 CA $1,643 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Lahaina-Hotels-Oceanview-Retreat-In-Puamana-Steps-From-The-Beach-Surf.h114567607.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/cf2106a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/1ae1d770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/a69ddfe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/8b9e6573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lahaina [](https://www.expedia.ca/Lahaina-Hotels-Oceanfront-Getaway-W-A-Furnished-Patio.h65856731.Hotel-Information) 9.6/10 Exceptional (9) "Very clean, stocked well, comfortable bed and furniture, enough storage for your items, food. Very nice view from entire unit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim K. CA $282 CA $808 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Lahaina-Hotels-Oceanfront-Getaway-W-A-Furnished-Patio.h65856731.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/6f547eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/a1cdd950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, stereo](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/6af12484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, internet](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/c5606309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in South Kihei [](https://www.expedia.ca/Kihei-Hotels-Kihei-Akahi-A102-Maui-Ocean-Front-Town-House-Location.h19007798.Hotel-Information) 9.2/10 Wonderful (61) CA $205 CA $812 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Kihei-Hotels-Kihei-Akahi-A102-Maui-Ocean-Front-Town-House-Location.h19007798.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/7ac65615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/5a11fc2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/4faa5508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/6e96bac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in North Kihei [](https://www.expedia.ca/Kihei-Hotels-Tropical-Garden-Family-Home-Sleeps-6-Walk-To-Beach.h33659703.Hotel-Information) 9.6/10 Exceptional (107) "Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael B. CA $682 CA $1,802 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Kihei-Hotels-Tropical-Garden-Family-Home-Sleeps-6-Walk-To-Beach.h33659703.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/7925e6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/4402a96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/44c47a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/54cfbcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lahaina [](https://www.expedia.ca/Lahaina-Hotels-Pualei-Beach-House-3-Bedroom-Townhome-In-Phenomenal-Lahaina-With-WiFi.h110998329.Hotel-Information) 10/10 Exceptional (4) "Wonderful experience. Loved the house... bathtub was excellent!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcy M. CA $764 CA $2,171 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Lahaina-Hotels-Pualei-Beach-House-3-Bedroom-Townhome-In-Phenomenal-Lahaina-With-WiFi.h110998329.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/28000000/27130000/27128400/27128361/b9c1435d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27128400/27128361/5389e30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27128400/27128361/9bfca475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27130000/27128400/27128361/9c505e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Haiku [](https://www.expedia.ca/Haiku-Hotels-Rainbow-Lookout-Private-Hot-Tub-Pool-Access-New-Central-Conditioning.h27128361.Hotel-Information) 10/10 Exceptional (24) "Amazing!!! Great location, amazing hosts, great hospitality! We absolutely loved our stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $874 CA $1,320 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Haiku-Hotels-Rainbow-Lookout-Private-Hot-Tub-Pool-Access-New-Central-Conditioning.h27128361.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/3d6a0b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, books](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/6cff8507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, books](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/06c203fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/64969ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lahaina [](https://www.expedia.ca/Napili-Hotels-Ocean-Front-Snorkel-With-Turtles.h100431711.Hotel-Information) 10/10 Exceptional (14) "Beautiful location and property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie A. CA $549 CA $1,460 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Napili-Hotels-Ocean-Front-Snorkel-With-Turtles.h100431711.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=2025-12-30&endDate=2025-12-31®ionId=553248621593965869&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpcountry-Maui-Private-Vacation-Homes.d553248621593965869-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpcountry-Maui-Private-Vacation-Homes.d553248621593965869-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Upcountry Maui Hotel Reviews ![Maui Beach Hotel](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg) ### Maui Beach Hotel 10/10 Excellent "Awesome staff awesome view couldn’t ask for more from this quaint cute hotel vibe!" [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.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 "staff are very friendly and easy to deal with and the hotel is clean " [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![The Westin Maui Resort & Spa, Ka'anapali](https://images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg) ### The Westin Maui Resort & Spa, Ka'anapali 10/10 Excellent "Great location, friendly staff, good amenities including restaurants amd pools. Hospitality room on last day was clean and available when needed." [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.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 "We had a wonderful stay at the resort. Staff was very accommodating and friendly, room was very clean and didn't have a musty smell like a lot of hotels do, and best of all, it was right in the middle of all the stuff to do in the area. I highly recommend staying there!" [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![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) ![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 "This has been an amazing vacation thanks to Whalers resort thanks to the awesome staff from the check inn to all the staff from the maintenance staff and all just can't say enough but we will certainly recommend as we are in the hospitality business and know what it takes to achieve a great and awesome experience to all Thank you MAHALO" [](https://expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.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) ## Find out more about Upcountry Maui ## Upcountry Maui Vacation Homes information | Number of reviews | 1,274 | | ----------------- | ------------------ | | Accommodation | 186 Vacation Homes | | Lowest Price | CA $359 | | Highest Price | CA $4,365 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Maui ](https://www.expedia.ca/5Star-Maui-Hotels.s50-0-d180073.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala Crater ](https://www.expedia.ca/Haleakala-Crater-Hotels.0-l501684-0.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala National Park ](https://www.expedia.ca/Haleakala-National-Park-Hotels.0-l507525-0.Travel-Guide-Filter-Hotels) - 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