Title: Upcountry Maui Vacation Home Rentals : 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 - ![](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 [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upcountry Maui Vacation Homes ![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) ![Exterior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/606a40d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 Makawao 10/10 Exceptional (70) "There is absolutely nothing we could think of that was missing from our week at Banyon Tree! The property is beautiful, lovingly maintained, and made this our best trip to Hawaii ever!! Actually, our best-ever family vacation! Plenty of room for swimming, playing Capture the Flag, enjoying family dinners, playing card and table games, and just hanging out. We enjoyed seeing the turtles at Ho’okepa Beach, playing in the river at Íao State Park, and shopping local markets. Comfortable island... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheridan B. CA $2,013 CA $3,920 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/1ceb2db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/1bd600e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/54d71ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/116000000/115740000/115732300/115732203/91ba7171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views! Haiku CA $743 CA $1,809 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Haiku-Hotels-2-Mi-To-Hana-Hwy-Haiku-Home-W-Ocean-Views.h115732203.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/3930425c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/7f0e124d.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) ![Exterior](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/e0e2bd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Haiku Hale - 3 Bedroom Maui Getaway! Haiku 10/10 Exceptional (4) "The neighborhood is a nice quiet area, with shops & places to eat within a minute walk. The driveway is a bit tricky, but opens up to a beautiful property with plenty of outdoor space. The house itself was very clean & neat, and the rooms all fit our needs. We only stayed one night but wish we could have stayed a week! I would highly recommend this property to anyone looking to stay off the beaten path but still be able to see everything you want!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nate G. CA $693 CA $1,373 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Haiku-Hale-3-Bedroom-Maui-Getaway.h97567999.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) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/c11638c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/70f3f0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 Hana 9.6/10 Exceptional (406) "Nice space with a good location. Comfy beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dannielle P. CA $244 CA $499 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/ced36266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 (9) "Loved having the hot tub to come home to!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pedro CA $150 CA $316 total includes taxes & fees Nov 17 - Nov 18 [](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) ![Exterior](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/700bd98f.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) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/33000000/32490000/32488600/32488569/446450bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b Hana 9.2/10 Wonderful (145) "We liked the flat very much. Clean, cosy, like described." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Petra W. CA $302 CA $695 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hana-Hotels-Beautiful-Home-In-The-Heart-Of-Hana.h32488569.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/963f0910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/71d86e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, DVD player, books](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/bd738079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/34000000/33400000/33394500/33394402/007570d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you! Hana 9.8/10 Exceptional (235) "Great place to stay if you are looking to get away from it all. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacques C. CA $410 CA $866 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/95afb621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/fff4e05a.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) ### 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006 Hana 9.8/10 Exceptional (76) "We had a very relaxing time at this property! Such a beautiful place. We will definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth C. CA $770 CA $1,387 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/97b49aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/7a8a41ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/1ac53446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/3b819fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In Paia 10/10 Exceptional (176) "Was pleasant and quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donovan W. CA $532 CA $1,343 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Paia-Hotels-Charming-Ocean-View-Home-With-Central-AC-Walk-To-Downtown-Paia-And-Beaches.h18973882.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/735ba3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/846341ea.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) ![TV](https://images.trvl-media.com/lodging/33000000/32650000/32643100/32643004/ce107928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hana Homestead by the Beach Hana 9.8/10 Exceptional (136) "The view from this house is absolutely amazing!! It overlooks Hana bay and the lighthouse. You can literally sit in the hot tub on the front porch and watch the sunset over the bay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah B. CA $707 CA $1,771 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Hana-Hotels-Hana-Homestead-By-The-Beach.h32643004.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/bb1d5416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/dd68c937.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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19010000/19007800/19007798/cd613688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!! South Kihei 9.2/10 Wonderful (60) "Everything you need in the condo and enough beaches to try one every day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marco D. CA $209 CA $827 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Kihei-Hotels-Kihei-Akahi-A102-Maui-Ocean-Front-Town-House-Location.h19007798.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) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/73f93779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/5a6cb0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/54ce5466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei North Kihei 9.8/10 Exceptional (109) "The property was clean, well maintained, and in a sweet, quiet neighborhood-a perfect home base for lots of day trips around Maui with tons of toys for beach-going. We hope to visit again! And a beautiful backyard and amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel C. CA $145 CA $705 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Kihei-Hotels-Tropical-Honeymoon-Suite-BBQ.h19667488.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/67f7c7a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/851adc8f.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) ![Interior](https://images.trvl-media.com/lodging/66000000/65860000/65856800/65856731/c618292d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront getaway with a furnished patio, views, pool, & high-speed WiFi Lahaina 9.6/10 Exceptional (9) "We greatly enjoyed our stay in this unit and on this property. The unit was exceptionally clean, well-maintained, and the kitchen was exceptional. The beds gave you the option of either a soft surface or a firm mattress. Excellent view from the lanai. And the snorkeling in Honokeana Bay was exceptional! Sea turtles galore! Will be back next year!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron W. [](https://www.expedia.ca/Lahaina-Hotels-Oceanfront-Getaway-W-A-Furnished-Patio.h65856731.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/9f8c163c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/5b5a9776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/101006ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanview Retreat in Puamana – Steps from the Beach & Surf Lahaina 10/10 Exceptional (2) "The condo was beautifully updated, very clean, and the furniture was comfortable. We loved the outdoor living space as well. We had everything we needed in the kitchen. The outdoor shower was a great extra! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren F. CA $421 CA $1,588 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lahaina-Hotels-Oceanview-Retreat-In-Puamana-Steps-From-The-Beach-Surf.h114567607.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/c173a4ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/19000000/19000000/18993100/18993062/0de8ef29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/08f40fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New! The Aloha Cottage in Puamana, Maui Hawaii Lahaina 9.8/10 Exceptional (86) "Loved our stay at the Aloha Cottage. Property was clean and neat. Kitchen was well stocked which made cooking for the kids easy. Loved the outdoor lanai. Great spot for families and kids. Easy close beach access, but also easy drive to stores and restaurants in Lahaina. Nearby beaches were also great. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra M. CA $371 CA $1,222 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Lahaina-Hotels-New-The-Aloha-Cottage-In-Puamana.h18993062.Hotel-Information) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/78000000/77090000/77088000/77087906/d5637ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/78000000/77090000/77088000/77087906/4dfeb9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77090000/77088000/77087906/988414be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77090000/77088000/77087906/39049279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views! Lahaina 10/10 Exceptional (27) "The house was perfect for our family of 5. We loved having beach items like chairs, umbrella, cooler, etc to use. Easy walk to the beach. The house had everything we needed! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jen B. CA $366 CA $1,230 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Kapalua-Hotels-Luxury-Panoramic-Ocean-Views.h77087906.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/84c3c2ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/cf2ae5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/7ac65615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33660000/33659800/33659703/d9b2ba99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub North Kihei 9.6/10 Exceptional (107) "Overall, this house was in a great location, clean and beautiful accommodations and superb customer service. From the moment we arrived, I was impressed by the cleanliness. The host made a note to greet us when we got there. He then showed us throughout the house to make sure we knew where everything was and answer any questions we had. Throughout the week, he was available to offer suggestions, and we saw a lot of great local sights based on his recommendations. This was one of the best houses... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin S. CA $353 CA $1,401 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Kihei-Hotels-Tropical-Garden-Family-Home-Sleeps-6-Walk-To-Beach.h33659703.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76800000/76792100/76792015/490942eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76800000/76792100/76792015/e30ec0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, video games, DVD player, books](https://images.trvl-media.com/lodging/77000000/76800000/76792100/76792015/cde6d3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76800000/76792100/76792015/45b62fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCEAN FRONT | POOL! Walk to the Beach! 3 KING BEDS Lahaina 10/10 Exceptional (26) "I looked around quite a bit and this property is everything they said it would be. Ocean right out the back door! I’m sure we will be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carl C. CA $631 CA $1,960 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Lahaina-Hotels-Ocean-Front-Walk-To-The-Beach.h76792015.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/22000000/21300000/21294100/21294019/948289a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21300000/21294100/21294019/418a3a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21300000/21294100/21294019/70e84365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21300000/21294100/21294019/a2019278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BD WALK TO SANDY BEACH | Gated | LUXURY SPA FEEL Lahaina 10/10 Exceptional (176) "We had an amazing time in Maui. The house was clean, well stocked and in a great location. Communication was extremely easy and quick! Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina E. CA $531 CA $1,432 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Kapalua-Hotels-Luxury-Vacation-Rental-Napili-Gardens-3-Bedrooms.h21294019.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/cd58bba9.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) ![Interior](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/087887b0.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) ### Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC Lahaina 10/10 Exceptional (3) "This place was exactly what our family (3 adults and 2 toddlers) needed. It was immaculately clean, walkable to a very private beach, and had everything needed for our stay to be perfect (toys, beach gear, towels, kitchen necessities, etc). We would 100% rebook " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael T. CA $566 CA $1,956 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Lahaina-Hotels-Pualei-Beach-House-3-Bedroom-Townhome-In-Phenomenal-Lahaina-With-WiFi.h110998329.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01®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 ### Royal Lahaina Resort & Bungalows 10/10 Excellent "Loved our experience " [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ### Maui Seaside Hotel 10/10 Excellent "Very clean, great helpful staff, stunning views of the mountains" [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ### Aston Kaanapali Shores 10/10 Excellent "Was a great place to stay" [](https://expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information) ### OUTRIGGER Kaanapali Beach Resort 10/10 Excellent "Got an upgraded room at no charge right on the beach. Bigger room , big shower , balcony. Comfortable bed too Friendly staff and beautiful beach. Close to whalers village for food and shopping. Pool in middle of resort with snack bar next to it. " [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ### Sheraton Maui Resort & Spa 10/10 Excellent "Enjoyed the hotel and the area around the hotel. Food and beach was great " [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ### Maui Beach Hotel 10/10 Excellent "Minnie was terrific at reception. Steered us right with everything from the room to where to walk to buy postcards (Longs Drugs)." [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ### The Westin Maui Resort & Spa, Ka'anapali 10/10 Excellent "Everything is good " [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ### Andaz Maui at Wailea Resort - a concept by Hyatt 10/10 Excellent "hotel providing a car to drive you anywhere in Wailea makes it very convenient. plus, having" [](https://expedia.ca/Kihei-Hotels-Andaz-Maui-At-Wailea-Resort-A-Concept-By-Hyatt.h2552.Hotel-Information) ### Fairmont Kea Lani Maui 10/10 Excellent "We stayed at the Fairmont Kea Lani for our honeymoon and from the moment we arrived everything was perfect. The lei and kukui nut necklaces were so fun and check in was a breeze, we were even able to check in early. Our room was huge and the ocean view from our balcony was a beautiful way to wake up every morning. Housekeeping was impeccable, the food was delicious and having a semi-private beach with chairs and umbrellas was amazing to sit and relax the day away. We also enjoyed the spa while we were there and the services we received were so relaxing, a perfect way to end our perfect honeymoon. We would definitely recomment the Fairmont Kea Lani and can't wait to come back again." [](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 | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## 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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