Title: Upcountry Maui Vacation Rentals from CA $449: Short-Term Rentals for 2025 | 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) ![](https://mediaim.expedia.com/destination/9/01b28fa5aec642d0f16d83dbe59a5809.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 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 In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [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 four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-30&endDate=2026-02-01&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) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.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) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 Makawao 10/10 Exceptional (70) "Amazing Property!! Host was very friendly and gracious with time for checking in and out. Our whole family wish we could have stayed longer. Perfect spot for all of our activities" [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/850ae64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/d3a6a1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/e69b613b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston Kaanapali Shores Lahaina 8.6/10 Excellent (3788) "Great stay" CA $447 CA $569 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.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) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/ebc7e42d.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) ![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) ### Aston Maui Kaanapali Villas Lahaina 8.8/10 Excellent (2469) "Beautiful quiet property on the beach with dining options and shopping a short walk or shuttle ride away" CA $318 CA $499 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lahaina-Hotels-Aston-Maui-Kaanapali-Villas.h18735.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/b85a7c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/747fb065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/84f4f2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whaler Resort Kaanapali Beach Lahaina 9.6/10 Exceptional (263) "Nice pool, sandy beach, easy parking in garage." CA $312 CA $902 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.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) ![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) ![Suite, 3 Bedrooms, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/fa899b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OUTRIGGER Honua Kai Resort & Spa Lahaina 8.8/10 Excellent (2846) "Great stay" CA $419 CA $1,137 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.Hotel-Information) ![Studio Suite | Living area](https://images.trvl-media.com/lodging/2000000/1800000/1797300/1797282/cc5dd277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand](https://images.trvl-media.com/lodging/2000000/1800000/1797300/1797282/e4dde35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1800000/1797300/1797282/15f77023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, toaster, paper towels](https://images.trvl-media.com/lodging/2000000/1800000/1797300/1797282/b86951df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kahana Falls Maui by VRI Americas Lahaina 8.0/10 Very good (938) "rooms were nice , clean, staff was friendly " [](https://www.expedia.ca/Lahaina-Hotels-Kahana-Falls-Maui.h1797282.Hotel-Information) ![Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/abca45f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/6918496a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tennis court](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/1a64b291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/78a25dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston Maui Hill South Kihei 9.0/10 Wonderful (834) "Beautiful, quiet place. Great location. " CA $436 CA $514 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Kihei-Hotels-Aston-Maui-Hill.h24554.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) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/beab4669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/a4fcedb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/3f3a315b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Napili Shores Maui by OUTRIGGER Lahaina 9.0/10 Wonderful (1674) "awesome stay!" CA $381 CA $449 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lahaina-Hotels-Napili-Shores-Maui-By-Outrigger.h27045.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/77000000/76470000/76469500/76469414/f4e1a439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76470000/76469500/76469414/d92052ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/77000000/76470000/76469500/76469414/1e407100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/77000000/76470000/76469500/76469414/b2e0fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014 Lahaina 10/10 Exceptional (266) "Great location. " CA $441 CA $984 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Kaanapali-Hotels-Mahana-At-Kaanapali.h76469414.Hotel-Information) ![Suite, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/1000000/10000/2500/2457/618976ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/1000000/10000/2500/2457/79b9c7c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/2500/2457/a376782a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 1 Bedroom | Balcony view](https://images.trvl-media.com/lodging/1000000/10000/2500/2457/7f58a3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maui Beach Vacation Club North Kihei 8.2/10 Very good (802) "Room was quiet, no ac but the breeze came through very nice. Comfortable and convenient location. " [](https://www.expedia.ca/Kihei-Hotels-Maui-Beach-Vacation-Club.h2457.Hotel-Information) ![Surfing/boogie boarding](https://images.trvl-media.com/lodging/1000000/70000/62200/62187/ad188258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, iron/ironing board](https://images.trvl-media.com/lodging/1000000/70000/62200/62187/b0199dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with satellite channels, TV](https://images.trvl-media.com/lodging/1000000/70000/62200/62187/be123924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Oceanfront | View from room](https://images.trvl-media.com/lodging/1000000/70000/62200/62187/db01e085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston at Papakea Resort Lahaina 8.2/10 Very good (1384) "Everything was excellent " [](https://www.expedia.ca/Kaanapali-Hotels-Aston-At-Papakea-Resort.h62187.Hotel-Information) ![Deluxe Condo, 3 Bedrooms | Balcony](https://images.trvl-media.com/lodging/1000000/30000/21100/21083/4531dc20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Condo, 1 Bedroom, 2 Bathrooms | Private kitchen](https://images.trvl-media.com/lodging/1000000/30000/21100/21083/d90cc698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Condo, 1 Bedroom, 2 Bathrooms](https://images.trvl-media.com/lodging/1000000/30000/21100/21083/acd6ffd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/30000/21100/21083/4adf0e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Kama'ole Sands South Kihei 8.0/10 Very good (2262) "Front desk was wonderful." [](https://www.expedia.ca/Kihei-Hotels-Castle-Kamaole-Sands.h21083.Hotel-Information) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/3738ec4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 3 Bedrooms, Non Smoking, Balcony (Oceanfront) | Living area](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/4fb32c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/ac39dd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Nanea Ocean Villas, Ka'anapali Lahaina 9.2/10 Wonderful (469) "Very nice place to stay" CA $671 CA $792 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Lahaina-Hotels-The-Westin-Nanea-Ocean-Villas.h16700689.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/70000/60400/60350/50e7296a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Penthouse, 2 Bedrooms, Oceanfront | Private kitchenette](https://images.trvl-media.com/lodging/1000000/70000/60400/60350/e6daf16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/70000/60400/60350/2a655f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/70000/60400/60350/7ba8ed2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston at The Whaler on Kaanapali Beach Lahaina 9.2/10 Wonderful (1492) "Great views spacy rooms " [](https://www.expedia.ca/Lahaina-Hotels-Aston-At-The-Whaler-On-Kaanapali-Beach.h60350.Hotel-Information) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/920000/917000/916906/49407e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/917000/916906/c8fddd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, 2 poolside bars](https://images.trvl-media.com/lodging/1000000/920000/917000/916906/890f2a9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/917000/916906/e2d7c19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Ka'anapali Ocean Resort Villas Lahaina 8.6/10 Excellent (1117) "Great location, lots of amenitie" CA $626 CA $739 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Lahaina-Hotels-The-Westin-Kaanapali-Ocean-Resort-Villas.h916906.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23360000/23357700/23357665/62a97d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom, Kitchen, Garden View | Private kitchen](https://images.trvl-media.com/lodging/24000000/23360000/23357700/23357665/5eaec25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23360000/23357700/23357665/1189ef32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom, Kitchen, Ocean View](https://images.trvl-media.com/lodging/24000000/23360000/23357700/23357665/200b7556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AEI at Kaanapali Shores Lahaina 8.8/10 Excellent (482) "Great vibes and amenities." [](https://www.expedia.ca/Lahaina-Hotels-AEI-At-Kaanapali-Shores.h23357665.Hotel-Information) ![Villa, 1 Bedroom, Oceanfront (Bay 36B3 Gold ,1Bath)](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/84e6455b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms, Oceanfront (Bay 19B2 Gold 2.5 bath) | In-room dining](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/2afbcc2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Oceanfront (Bay 26G2 Gold ,1Bath) | Private kitchen](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/cdef340e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms, Oceanfront (Bay 19B2 Gold 2.5 bath) | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/dd10699a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kapalua Villas Maui Lahaina 8.8/10 Excellent (955) "Gorgeous property, the staff, beach, hiking close by, restaurants in area all were great. Room was spotless and we were able to check in early." CA $313 CA $1,112 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Lahaina-Hotels-Kapalua-Villas-Maui.h22419.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/12900/12900/5b79233d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12900/12900/e0657210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12900/12900/7a716c57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Studio, Kitchen, Oceanfront](https://images.trvl-media.com/lodging/1000000/20000/12900/12900/a3f3e6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston Mahana at Kaanapali Kaanapali 9.0/10 Wonderful (1671) "Great views and amazing beach to snorkel " [](https://www.expedia.ca/Lahaina-Hotels-Aston-Mahana-At-Kaanapali.h12900.Hotel-Information) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/3000000/2670000/2668300/2668250/79d54f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/3000000/2670000/2668300/2668250/cfb8ec66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/3000000/2670000/2668300/2668250/1fb860f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2670000/2668300/2668250/24fae213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gardens at West Maui Lahaina 8.6/10 Excellent (502) "Great for family! " [](https://www.expedia.ca/Kapalua-Hotels-The-Gardens-At-West-Maui.h2668250.Hotel-Information) ![Standard Room, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/20000/13100/13039/4a7e4f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/20000/13100/13039/390a5d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/13100/13039/f3bf9344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/13100/13039/19d3719a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kahana Beach Vacation Club Lahaina 8.4/10 Very good (729) "Beautiful view! I would definitely stay there again. " [](https://www.expedia.ca/Kahana-Hotels-Kahana-Beach-Vacation-Club.h13039.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=2025-10-26&endDate=2025-10-27®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-Vacation-Rentals.d553248621593965869.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpcountry-Maui-Vacation-Rentals.d553248621593965869.Travel-Guide-VacationRentals) ## Top Upcountry Maui Hotel Reviews ![Aston Kaanapali Shores](//images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615_y.jpg) ### Aston Kaanapali Shores 10/10 Excellent "The staff were very helpful and were able to accommodate us for an early check in. We were very pleased with our room, and the grounds around the hotel are beautiful. I loved that it was right on the beach which ended up being a pretty good beach for us. We even saw 3 turtles while snorkeling there! The only thing we weren’t prepared for was how noisy the Myna birds were! They were squawking even in the middle of the night!" [](https://expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information) ![Hyatt Regency Maui Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19300/19207/3102d1ec_y.jpg) ### Hyatt Regency Maui Resort & Spa 10/10 Excellent "Nice staff, rooms were clean and I like the option to opt out of housecleaning for a refund. " [](https://expedia.ca/Lahaina-Hotels-Hyatt-Regency-Maui.h19207.Hotel-Information) ![The Westin Maui Resort & Spa, Ka'anapali](//images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg) ### The Westin Maui Resort & Spa, Ka'anapali 10/10 Excellent "Room and view were great. Staff was EXCELLENT. Pool outstanding." [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](//images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "The property is beautiful " [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.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 "Yes. Higher floor would have been better but still the view was amazing." [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.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 "excellent" [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Aston Maui Kaanapali Villas](//images.trvl-media.com/lodging/1000000/20000/18800/18735/6389d34f_y.jpg) ### Aston Maui Kaanapali Villas 10/10 Excellent "Early check ins are not an option. The staff sent mixed messages about checking in. Not pleased, the resort was really nice. " [](https://expedia.ca/Lahaina-Hotels-Aston-Maui-Kaanapali-Villas.h18735.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 "beautiful views and good location." [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![AEI at Maui Kaanapali Villas Resort](//images.trvl-media.com/lodging/58000000/57720000/57713500/57713484/6bf5bf4d_y.jpg) ### AEI at Maui Kaanapali Villas Resort 10/10 Excellent "It was soo relaxing and clean. I had a hard time being able to check in early but after our stay we had such a great time there. Loved it would definitely come back again" [](https://expedia.ca/Lahaina-Hotels-AEI-At-Maui-Kaanapali-Villas-Resort.h57713484.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 $449 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 - Trending destinations on Expedia.ca - All accommodation types in Upcountry Maui ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Condo Rentals in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Condos.d553248621593965869-aaCondos.Travel-Guide-Accommodation) - [Vacation Homes in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Private-Vacation-Homes.d553248621593965869-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Apartments.d553248621593965869-aaApartments.Travel-Guide-Accommodation) - [Villas in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Villas.d553248621593965869-aaVillas.Travel-Guide-Accommodation) - [Resorts in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Resort-Hotels.d553248621593965869-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Apart-Hotels.d553248621593965869-aaApartHotels.Travel-Guide-Accommodation) - [Cottages in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Cottages.d553248621593965869-aaCottages.Travel-Guide-Accommodation) - [B&B in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Bed-And-Breakfast.d553248621593965869-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Resorts in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Condominium-Resort.d553248621593965869-aaCondominiumResort.Travel-Guide-Accommodation) - [Guest Houses in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Guest-Houses.d553248621593965869-aaGuestHouses.Travel-Guide-Accommodation) - [Hostels in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Hostels.d553248621593965869-aaHostels.Travel-Guide-Accommodation) - [Farmstay in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Agritourism.d553248621593965869-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in Upcountry Maui](https://expedia.ca/Upcountry-Maui-Cabins.d553248621593965869-aaCabins.Travel-Guide-Accommodation) ### Expedia's Latest Trends Hotels - [Hotels in Maui](https://expedia.ca/Maui-Hotels.d180073.Travel-Guide-Hotels) - [Hotels in Kauai](https://expedia.ca/Kauai-Hotels.d180075.Travel-Guide-Hotels) - [Hotels in Oahu](https://expedia.ca/Oahu-Hotels.d180077.Travel-Guide-Hotels) - [Hotels with Childcare in Maui](https://expedia.ca/Maui-Hotels-Hotels-With-Childcare.0-0-d180073-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and Hotels in Maui](https://expedia.ca/Maui-Hotels-All-Inclusive-Hotel.0-0-d180073-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and Hotels in Kauai](https://expedia.ca/Kauai-Hotels-All-Inclusive-Hotel.0-0-d180075-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Hotels in North Shore](https://expedia.ca/North-Shore-Hotels.d6048743.Travel-Guide-Hotels) - [Cheap Hotels in Oahu](https://expedia.ca/Oahu-Hotels-Cheap-Hotels.0-0-d180077-tCheapHotels.Travel-Guide-Filter-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 - [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) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app 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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)