Title: Upcountry Maui Vacation Home Rentals from CA $323: 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) ![](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 In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upcountry Maui Vacation Homes ![Garden](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/ced36266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Apartment, Garden View (Haiku #2) | Living area](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/6bb7cdbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Apartment, Garden View (Haiku #2)](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/4e5368b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/f9c6c56b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yonegan Maui Getaways - Haiku Haiku 9.2/10 Wonderful (5) "Loved having the hot tub to come home to!!" CA $157 CA $323 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Haiku-Hotels-Yonegan-Maui-Getaways-Haiku.h117919946.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/530ff241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/2f01dccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/70f3f0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/c11638c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 Hana 9.6/10 Exceptional (401) "The property was excellent, highly recommend. " CA $242 CA $496 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/51ee3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/25e08687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/58ae806d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/a42f39cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher's Hana Bay Hale, Across from Hana Bay Kahului 9.4/10 Exceptional (405) "Wonderful property and a great place to stay in Hana" CA $272 CA $553 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/91000000/90930000/90926300/90926278/a9c5f68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90930000/90926300/90926278/6cc8d1f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90926300/90926278/3f525825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90930000/90926300/90926278/f0d99547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches! Hana 9.6/10 Exceptional (20) "Great place, very convenient and amazing settings! " [](https://www.expedia.ca/Hana-Hotels-Amazing-Hana-Bay-Beach-Cottage-Location-5-Minute-Walk-To-Hana-Town-Beaches.h90926278.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/20000000/19390000/19383600/19383551/b10b0f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19390000/19383600/19383551/b536689d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19390000/19383600/19383551/bb315fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19390000/19383600/19383551/05aa2d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Privacy In Paradise - Top Rated Vacation Home in West Maui Lahaina 10/10 Exceptional (143) "It was simply amazing" [](https://www.expedia.ca/Launiupoko-Hotels-Privacy-In-Paradise-Top-Rated-Vacation-Home-In-West-Maui.h19383551.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32080000/32075900/32075830/b1e6d341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32080000/32075900/32075830/8caf2bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, video games](https://images.trvl-media.com/lodging/33000000/32080000/32075900/32075830/49f18d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/33000000/32080000/32075900/32075830/2e7dcf45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC Halama Street 10/10 Exceptional (129) "Plenty of room. Great kitchen for lots of cooks." [](https://www.expedia.ca/Kihei-Hotels-Gorgeous-Home-Across-From-Beach-5-BR-Opt-Cottage-4-Bath-AC.h32075830.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33510000/33502500/33502441/ee1ae96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, table tennis](https://images.trvl-media.com/lodging/34000000/33510000/33502500/33502441/3790f915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, in-room safe, travel crib, free WiFi](https://images.trvl-media.com/lodging/34000000/33510000/33502500/33502441/13b936e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33510000/33502500/33502441/58fcc754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach Lahaina 9.8/10 Exceptional (154) "A great family destination. The grand kids spent hours in the pool. " [](https://www.expedia.ca/Kaanapali-Hotels-Spectacular-Sunset-And-Ocean-Views-With-Pool-Hotbub-Near-Kaanapali-Beach.h33502441.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29640000/29634400/29634389/c85a6b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29640000/29634400/29634389/54f0efcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29634400/29634389/c1993476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/30000000/29640000/29634400/29634389/173e825c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct! Lahaina 9.8/10 Exceptional (100) "This home is absolutely beautiful and accommodated our family of 25 well! It’s a block from the beach and has a great pool for kids of all ages! We loved our stay! " [](https://www.expedia.ca/Lahaina-Hotels-Voted-The-1-Vacation-Rental-On-Maui-Brand-New-30-Steps-To-Mauis-Best-Beach.h29634389.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34090000/34081200/34081190/19a51817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/35000000/34090000/34081200/34081190/05636d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34090000/34081200/34081190/981a05da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/35000000/34090000/34081200/34081190/1fe59b4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCEANFRONT PUAMANA 136-1 - FUN IN THE SUN! Lahaina 10/10 Exceptional (74) "The location was stunning as well as the property itself. The owner was quick to respond to questions and was flexible with my schedule. Very clean and absolutely gorgeous! " [](https://www.expedia.ca/Lahaina-Hotels-Puamana-136-1-FUN-IN-THE-Sun.h34081190.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33960000/33957600/33957562/35096fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33957600/33957562/31e97cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/34000000/33960000/33957600/33957562/302e6782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33960000/33957600/33957562/c98aaa73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area Wailea 10/10 Exceptional (86) "Maui Meadows Guesthouse is spectacular. The private pool and spa with waterfall are its own little paradise. The location is in a quiet neighborhood with quick access to beaches, restaurants and island activities. Andrew our host is helpful, quick to respond and meticulous. From the backyard porch swing for Grandpa to the toy drawer for our Grandson, this house provides comfort and relaxation for all. We hope you enjoy your stay as much as we have." [](https://www.expedia.ca/Kihei-Hotels-Amazing-House-With-Pool.h33957562.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33700000/33694800/33694798/5ce15445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33700000/33694800/33694798/d17c90ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/34000000/33700000/33694800/33694798/bdb182f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33700000/33694800/33694798/ef6df49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center Wailea 9.8/10 Exceptional (103) "Beautiful property" [](https://www.expedia.ca/Kihei-Hotels-Newly-Renovated-Closest-To-Hoolei-Pool.h33694798.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118990000/118982300/118982223/89c47593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/119000000/118990000/118982300/118982223/6075b1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118990000/118982300/118982223/8ebb7197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118990000/118982300/118982223/fb4f3a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views Kihei [](https://www.expedia.ca/Kihei-Hotels-Topfloor-Oceanview-Menuhene-Shores-604.h118982223.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) ![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) ![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) ### #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) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45480000/45477600/45477544/eae1d6e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/46000000/45480000/45477600/45477544/90-4911d242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45480000/45477600/45477544/5009785a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/46000000/45480000/45477600/45477544/58efc43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kihei Maui Beach house - On the water Halama Street 9.8/10 Exceptional (58) "Mark was wonderful to work with. Some things could use some updates but overall it was a great location and we had a great stay." [](https://www.expedia.ca/Kihei-Hotels-Kihei-Maui-Beach-House-On-The-Water.h45477544.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/5000000/4600000/4595700/4595613/fb4045d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hibiscus Suite](https://images.trvl-media.com/lodging/5000000/4600000/4595700/4595613/a258e356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hibiscus Suite | Bathroom amenities](https://images.trvl-media.com/lodging/5000000/4600000/4595700/4595613/11d63300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Orchid Suite | Private kitchen](https://images.trvl-media.com/lodging/5000000/4600000/4595700/4595613/fbccc477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kaiholo Hale Paia 9.4/10 Exceptional (200) "Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation." [](https://www.expedia.ca/Paia-Hotels-Kaiholo-Hale.h4595613.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/49000000/48450000/48443800/48443780/a73dfb67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48450000/48443800/48443780/02028894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48450000/48443800/48443780/ccd1f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48450000/48443800/48443780/ec12c87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The #1 Luxury OCEAN FRONT Mansion! Sleeps 32 lahina 9.8/10 Exceptional (78) "Really enjoyed this home! " [](https://www.expedia.ca/Lahaina-Hotels-1-Rated-Luxury-Ocean-Front-Mansion-Sleeps-32.h48443780.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/102000000/101900000/101897700/101897652/4240e0a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101900000/101897700/101897652/469714d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101900000/101897700/101897652/bc3ad5bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/102000000/101900000/101897700/101897652/55440a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym! Lahaina 9.8/10 Exceptional (23) "What a great property to stay with the family. Enough room for everyone and the proximity to dining, shopping and golf was amazing " [](https://www.expedia.ca/Napili-Hotels-Celebrity-Estate.h101897652.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19010000/19007600/19007583/606d0e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19007600/19007583/29c1ea75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/20000000/19010000/19007600/19007583/ec3eb9cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19010000/19007600/19007583/86e55df4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view Kihei 9.8/10 Exceptional (204) "Perfect home for a large group. Beach is across the street the back to the pool when the waves got to be to much for our little ones. Great property manager! Great location! " [](https://www.expedia.ca/Kihei-Hotels-Tropical-Gated-Oceanfront-Estate.h19007583.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/36000000/35670000/35669500/35669434/3fa1e769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35670000/35669500/35669434/83171d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35670000/35669500/35669434/ed3652df.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/36000000/35670000/35669500/35669434/1c127de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HALE NUI Luxury Retreat 5BD w Private Pool Hot Tub Lahaina 10/10 Exceptional (84) "The house was amazing and the location perfect! The view was unforgettable!! " [](https://www.expedia.ca/Kaanapali-Hotels-HALE-NUI-Luxury-Retreat-5BD-W-Private-Pool-Hot-Tub.h35669434.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/67000000/66180000/66179400/66179304/1435ac08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66180000/66179400/66179304/2fb059d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/67000000/66180000/66179400/66179304/055ecba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66180000/66179400/66179304/dbed3509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exceptional Upcountry Villa with breathtaking views Makawao 10/10 Exceptional (44) "Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. " [](https://www.expedia.ca/Makawao-Hotels-Luxury-Upcountry-Villa-With-Breathtaking-Views.h66179304.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=2025-10-12&endDate=2025-10-13®ionId=553248621593965869&adults=2&lodging=VACATION_HOME&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-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 ![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 "Beautiful views and very clean. The staff are very nice. " [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.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 "Nice pool, sandy beach, easy parking in garage." [](https://expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.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 "Great Hotel with great facilities" [](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 "We had an AMAZING time on our stay, the room Was beautiful, view was spectacular, staff was so sweet and friendly. Can’t recommend it enough! Easy transportation via free shuttle the the nearby resorts and whalers village. Overall great place to stay!" [](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 "I like the service but the cleaning could have been better. It was quite but charged for every little fees including sometimes credit card fees" [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Hilton Vacation Club Ka'anapali Beach Maui](//images.trvl-media.com/lodging/1000000/30000/23100/23042/7a9e8592_y.jpg) ### Hilton Vacation Club Ka'anapali Beach Maui 10/10 Excellent "Great room great service employees were awesome overall it was a great quiet calm stay. No drunken people no drama just straight out great place to get away and relax." [](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.Hotel-Information) ![Maui Coast Hotel](//images.trvl-media.com/lodging/1000000/30000/28700/28645/ffbd6b5d_y.jpg) ### Maui Coast Hotel 10/10 Excellent "We love Maui Coast Hotel. We were here this same time last year and were excited to know exactly where we wanted to stay! We love everything about this hotel!" [](https://expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.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 "Excellent service & stay!" [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![Four Seasons Resort Maui at Wailea](//images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg) ### Four Seasons Resort Maui at Wailea 10/10 Excellent "Beautiful resort. Everything was absolutely perfect. Room was impeccable. Staff were very friendly and accommodating. Pool and beach area were really nice. Will stay here again. " [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ## Find out more about Upcountry Maui ## Upcountry Maui Vacation Homes information | Number of reviews | 2,141 | | --- | --- | | Accommodation | 179 Vacation Homes | | Lowest Price | CA $323 | | Highest Price | CA $553 | ## 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) - [Hotels near Haleakalā Visitor Center](https://www.expedia.ca/Haleakala-Visitor-Center-Hotels.0-l553248621526965459-0.Travel-Guide-Filter-Hotels) - [Condo Rentals in Kahakuloa](https://www.expedia.ca/Kahakuloa-Condos.d11822-aaCondos.Travel-Guide-Accommodation) - 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