Title: Upcountry Maui Vacation Rentals from CA $409: 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 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Tonight [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-09-23&endDate=2025-09-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-03&endDate=2025-10-05&adults=2&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) ![Exterior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/606a40d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/93574a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 Makawao 10/10 Exceptional (68) "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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1300/1284/d3a6a1f5.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) ![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 (3749) "We had an amazing stay and cannot wait to book our next vacation with them!!" CA $356 CA $461 total includes taxes & fees Sep 29 - Sep 30 [](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) ![50-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/f2a689e8.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) ![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) ### Aston Maui Kaanapali Villas Lahaina 8.8/10 Excellent (2460) "Great family resort! Huge room that was perfect for our family of 5. 2 bedrooms and a huge kitchen/living room made for the perfect staycation on Island. " CA $314 CA $493 total includes taxes & fees Sep 30 - Oct 1 [](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) ![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) ![Outdoor pool](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/747fb065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, Multiple Beds, Oceanfront (2 Baths) | Living area](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/2f70d75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whaler Resort Kaanapali Beach Lahaina 9.6/10 Exceptional (243) "We had a lovely stay! I would recommend this place especially for honeymooners. " CA $308 CA $890 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.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) ![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) ![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) ### Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014 Lahaina 10/10 Exceptional (265) "Great location. " CA $491 CA $1,046 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Kaanapali-Hotels-Mahana-At-Kaanapali.h76469414.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/2000000/1800000/1797300/1797282/604bffa7.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) ### Kahana Falls Maui by VRI Americas Lahaina 8.0/10 Very good (927) "Great place! The staff was very nice and the property was very cute! Loved the waterfall pool " [](https://www.expedia.ca/Lahaina-Hotels-Kahana-Falls-Maui.h1797282.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 (2838) "Very clean and convenient, great location and great beaches" CA $439 CA $1,151 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.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) ![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, 1 King Bed, Ocean View | Private kitchenette](https://images.trvl-media.com/lodging/1000000/30000/24600/24554/48af28ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, 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) ### Aston Maui Hill Kihei 9.0/10 Wonderful (827) "Very nice and budget friendly." CA $414 CA $488 total includes taxes & fees Oct 24 - Oct 25 [](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) ![Courtyard](https://images.trvl-media.com/lodging/1000000/30000/27100/27045/3f3a315b.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) ### Napili Shores Maui by OUTRIGGER Lahaina 9.0/10 Wonderful (1666) "The location was great to restaurants and the beach." CA $347 CA $409 total includes taxes & fees Sep 27 - Sep 28 [](https://www.expedia.ca/Lahaina-Hotels-Napili-Shores-Maui-By-Outrigger.h27045.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) ![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) ![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) ![Penthouse, 2 Bedrooms, Oceanfront | Living room](https://images.trvl-media.com/lodging/1000000/70000/60400/60350/4f2929c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston at The Whaler on Kaanapali Beach Lahaina 9.2/10 Wonderful (1487) "Clean with a beach view nice gym and pool " [](https://www.expedia.ca/Lahaina-Hotels-Aston-At-The-Whaler-On-Kaanapali-Beach.h60350.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) ![Family Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/10000/2500/2457/b5cf350f.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) ### Maui Beach Vacation Club Kihei 8.2/10 Very good (798) "Just a great stay! " [](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) ![2 outdoor pools](https://images.trvl-media.com/lodging/1000000/70000/62200/62187/39a08668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, 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 (1383) "Everything was excellent " [](https://www.expedia.ca/Kaanapali-Hotels-Aston-At-Papakea-Resort.h62187.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) | 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) ![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, 1 Bedroom, Ocean Front (Bay 18G3, Gold, 1.5 Bath) | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/98889b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kapalua Villas Maui Lahaina 8.8/10 Excellent (952) "The view of the ocean was great and I was happy just to be there. It was old and a little poorly built, windows or doors were hard to open, etc. Some renovated parts were comfortable. The dryer was broken, which was inconvenient, but housekeeping provided new towels daily and offered to do laundry for free. Cooking utensils were very well stocked" CA $289 CA $1,072 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Lahaina-Hotels-Kapalua-Villas-Maui.h22419.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/e2d7c19d.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) ### The Westin Ka'anapali Ocean Resort Villas Lahaina 8.6/10 Excellent (1114) "The resort was beautiful. The hospitality in all seas was top notch. " CA $618 CA $729 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Lahaina-Hotels-The-Westin-Kaanapali-Ocean-Resort-Villas.h916906.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/107000000/106960000/106957200/106957113/79d9202b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106960000/106957200/106957113/1cdf3b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106960000/106957200/106957113/8f09e2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/107000000/106960000/106957200/106957113/e58eda32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool Lahaina 10/10 Exceptional (12) "We had an amazing vacation with our kids and grandkids. We have already booked again for next year" [](https://www.expedia.ca/Kaanapali-Hotels-1-Direct-Ocean-Front-Mansion-Pickleball.h106957113.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) ![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) ![Standard Condo, 1 Bedroom, 2 Bathrooms | In-room dining](https://images.trvl-media.com/lodging/1000000/30000/21100/21083/89d61bf2.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) ### Castle Kama'ole Sands Kihei 8.0/10 Very good (2256) " Loved the grounds, full of beautiful tropical plantings. Nice pool area and places to grill outdoors. All building have lanais with tables. Only a short walk to the beach and the Pacific ocean. Great sunsets!" [](https://www.expedia.ca/Kihei-Hotels-Castle-Kamaole-Sands.h21083.Hotel-Information) ![Premium Condo, 2 Bedrooms, Kitchen, Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/28500/28425/94a746a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Condo, 1 Bedroom, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/1000000/30000/28500/28425/5aed38fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/1000000/30000/28500/28425/c5ba39f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Condo, 1 Bedroom, Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/30000/28500/28425/495bbfa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maui Sunset Kihei 8.8/10 Excellent (473) "Good place to spend your vacation " [](https://www.expedia.ca/Kihei-Hotels-Maui-Sunset.h28425.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) ![Exterior](https://images.trvl-media.com/lodging/17000000/16710000/16700700/16700689/6b7c1eb2.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/17000000/16710000/16700700/16700689/78ae7ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Nanea Ocean Villas, Ka'anapali Lahaina 9.2/10 Wonderful (468) "Very nice place to stay" CA $773 CA $912 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Lahaina-Hotels-The-Westin-Nanea-Ocean-Villas.h16700689.Hotel-Information) ![Condo (2 Bedrooms) | View from room](https://images.trvl-media.com/lodging/100000000/99380000/99375300/99375280/7e45c8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms)](https://images.trvl-media.com/lodging/100000000/99380000/99375300/99375280/40aa7186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms)](https://images.trvl-media.com/lodging/100000000/99380000/99375300/99375280/9170fba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/100000000/99380000/99375300/99375280/5182f662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Honua Kai Konea Resort by KBM Kaanapali 9.6/10 Exceptional (60) "Beautiful views, ambiance’s, pool, rooms everything what we needed." [](https://www.expedia.ca/Kaanapali-Hotels-Honua-Kai-Konea-Resort-By-KBM.h99375280.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) ![Standard Room, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/20000/13100/13039/bdf6c03c.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) ![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) ### Kahana Beach Vacation Club Lahaina 8.4/10 Very good (717) "Great place to stay " [](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=2025-10-07&endDate=2025-10-08®ionId=553248621593965869&adults=2&sort=RECOMMENDED&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 ![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 "Absolutely beautiful from the open lobby area with the waterfall to the koi ponds and the exotic birds to the extensive pool area and beyond. This hotel took our breath away when we walked in. We enjoyed the view from our garden view room. We went to 3 islands and this was our favorite hotel. Great restaurants, walking distance to a shopping center with more great restaurants, Starbucks onsite, and a convenient grab and go/made to order fast food type option. Beach was right beyond the pool area. Great valet - quick service. Highly recommend!" [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![Aston Kaanapali Shores](//images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615_y.jpg) ### Aston Kaanapali Shores 10/10 Excellent "Everything is great" [](https://expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information) ![The Whaler Resort Kaanapali Beach](//images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/b85a7c13_y.jpg) ### The Whaler Resort Kaanapali Beach 10/10 Excellent "Great Resort. Close to food and shopping." [](https://expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.Hotel-Information) ![Maui Coast Hotel](//images.trvl-media.com/lodging/1000000/30000/28700/28645/ffbd6b5d_y.jpg) ### Maui Coast Hotel 10/10 Excellent "This place was great. Very clean. Staff was awesome. Felt safe there. Wonderful salt water pool.Close to everything you need. I will definitely stay here again " [](https://expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.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 "Beautiful property!" [](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 "Amazing location and very nicely upgraded hotel. " [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.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 "The overall surroundings was quiet and peaceful. The beach felt private at times. Not crowded like Waikiki beach in Oahu. We definitely prefer Maui more now. Our honeymoon in Hyatt Regency Maui Resort was a dream. Thank You" [](https://expedia.ca/Lahaina-Hotels-Hyatt-Regency-Maui.h19207.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 "I like how they had a gift in our room to congratulate us on our wedding " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![Wailea Beach Resort - Marriott, Maui](//images.trvl-media.com/lodging/1000000/30000/20400/20303/b323b293_y.jpg) ### Wailea Beach Resort - Marriott, Maui 10/10 Excellent "It was gorgeous; beautiful property, newly renovated, unbeatable views, and excellent service. Fantastic location as well; restaurants, shopping, beautiful trails, and beaches all within walking distance. Gorgeous pools as well, and lots of great activities for families, couples, solo travelers, or friends!" [](https://expedia.ca/Kihei-Hotels-Wailea-Beach-Resort-Marriott.h20303.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 $409 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) - 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