Title: Upcountry Maui Vacation Home Rentals from CA $342: 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) ![Haleakala National Park showing desert views](https://images.trvl-media.com/place/507525/6807006c-364a-44df-b5bd-8190e41c30e2.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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-03-20&endDate=2026-03-22&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) ![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 (71) "This property was indescribable! Our stay was amazing and the host was so very accommodating! Check-in was a breeze and every room was meticulously cleaned, arranged, and ready for our group. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James B. CA $2,015 CA $4,160 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/3930425c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97570000/97568000/97567999/bd3af031.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) ![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) "Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda S. CA $941 CA $1,697 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Haiku-Hale-3-Bedroom-Maui-Getaway.h97567999.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/51ee3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/a42f39cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720200/22720139/f7f2f5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Fisher's Hana Bay Hale, Across from Hana Bay Hana Town Center 9.6/10 Exceptional (409) "We only stayed one night but it was fantastic, clean and cozy! Check in was super simple and we were able to get in and out quickly to enjoy the rest of our trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jarah A. CA $274 CA $557 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Hana-Hotels-Fishers-Hana-Bay-Hale.h22720139.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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117920000/117919946/f9c6c56b.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) ### 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 $172 CA $342 total includes taxes & fees Dec 4 - Dec 5 [](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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22730000/22722300/22722218/55a71571.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 Town Center 9.6/10 Exceptional (410) "Great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony A. CA $244 CA $500 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Hana-Hotels-STHA-20170002-Across-From-Hana-Bay.h22722218.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) ![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) ![Smart TV, stereo](https://images.trvl-media.com/lodging/50000000/49220000/49216300/49216296/w1242h1656x0y276-798b978b.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) ### 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006 Kaʻeleku 9.8/10 Exceptional (76) "Phenomenal property for your stay in Hana - especially for a large group " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Logan G. CA $771 CA $1,382 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Hana-Hotels-3-Bedroom-Ocean-View-Private-Home-In-Hana-PermitSUP2-20190006.h49216296.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! Kaʻeleku 9.8/10 Exceptional (235) "Great property and excellent location with a perfect balance between privacy and proximity to Hana. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael T. CA $442 CA $909 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Hana-Hotels-Special-Quiet.h33394402.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) ![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) ![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) ### Hana Homestead by the Beach Hana Town Center 9.8/10 Exceptional (136) "This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $687 CA $1,737 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Hana-Hotels-Hana-Homestead-By-The-Beach.h32643004.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/2f8ffeb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/54ce5466.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) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19670000/19667500/19667488/0436179b.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) "This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Troy s. CA $119 CA $663 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Kihei-Hotels-Tropical-Honeymoon-Suite-BBQ.h19667488.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/32000000/31910000/31908600/31908561/962154b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31910000/31908600/31908561/b145b308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31910000/31908600/31908561/bdf8b246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/32000000/31910000/31908600/31908561/32a9e44a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★Star Honeymoon Lookout - PRIVATE HOT TUB + ACCESS TO POOL + New Central AC✔ Haiku 9.8/10 Exceptional (14) "Highly recommended " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaena [](https://www.expedia.ca/Haiku-Hotels-Star-Honeymoon-Lookout-PRIVATE-HOT-TUB-ACCESS-TO-POOL-New-Central-AC.h31908561.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) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993062/08f40fac.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) ### New! The Aloha Cottage in Puamana, Maui Hawaii Lahaina 9.8/10 Exceptional (86) "Cottage was clean and well kept. Location is convenient to shopping, dining, and many beaches including a small beach just a short walk from the property. Stay was very enjoyable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert B. CA $321 CA $1,157 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Lahaina-Hotels-New-The-Aloha-Cottage-In-Puamana.h18993062.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) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/3b819fea.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) ### Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In Paia 10/10 Exceptional (177) "Nice, clean and roomy place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosalina D. CA $532 CA $1,344 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) ![Pool](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/fc8f8feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/115000000/114570000/114567700/114567607/827bfa62.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) ![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) ### Oceanview Retreat in Puamana – Steps from the Beach & Surf Lahaina 10/10 Exceptional (2) "This property had everything you would want in a vacation home. Great location. We enjoyed the beach, community pool and grounds. The photos were exactly as pictured. We had a great time in your home. Thank you for hosting us." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joey M. CA $421 CA $1,538 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Lahaina-Hotels-Oceanview-Retreat-In-Puamana-Steps-From-The-Beach-Surf.h114567607.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) ![Interior](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/087887b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/44c47a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/111000000/111000000/110998400/110998329/54cfbcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC Lahaina 10/10 Exceptional (3) "Wonderful experience. Loved the house... bathtub was excellent!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcy M. CA $470 CA $1,812 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lahaina-Hotels-Pualei-Beach-House-3-Bedroom-Townhome-In-Phenomenal-Lahaina-With-WiFi.h110998329.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) ![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/34000000/33660000/33659800/33659703/261ae552.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) "Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael B. CA $354 CA $1,403 total includes taxes & fees Nov 28 - Nov 29 [](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) ![Dining](https://images.trvl-media.com/lodging/77000000/76800000/76792100/76792015/c5f2489d.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) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76800000/76792100/76792015/20b45491.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) "We loved our stay in Puamana. The unit was clean and well stocked. Being right on the water was magical. We would rent this unit again in a heartbeat." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) clark r. CA $581 CA $1,859 total includes taxes & fees Dec 11 - Dec 12 [](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) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/22000000/21300000/21294100/21294019/2e2e49f4.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) ![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) ### 3BD WALK TO SANDY BEACH | Gated | LUXURY SPA FEEL Lahaina 10/10 Exceptional (176) "Great place to stay and within walking distance to the best beaches. Very clean and had everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Krissi T. CA $508 CA $1,403 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Kapalua-Hotels-Luxury-Vacation-Rental-Napili-Gardens-3-Bedrooms.h21294019.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/42000000/41040000/41040000/41039947/4beb606b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41040000/41040000/41039947/e479bd79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/42000000/41040000/41040000/41039947/11de7d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/42000000/41040000/41040000/41039947/49521704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub North Kihei 10/10 Exceptional (2) "The house is an easy walk to a quiet beach and any easy drive to a grocery store and restaurants. The house was clean and well stocked. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly F. CA $538 CA $1,907 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Kihei-Hotels-Support-Local-Private-Tropical-Home-Jacuzzi-Penthouse.h41039947.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/64969ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/0a8a1335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/5da62082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/101000000/100440000/100431800/100431711/a6613b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### POOL & OCEAN VIEW | LUXURY | Snorkel With Turtles! Lahaina 10/10 Exceptional (13) "Beautiful location and property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie A. CA $585 CA $1,243 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Napili-Hotels-Ocean-Front-Snorkel-With-Turtles.h100431711.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/118000000/117520000/117517600/117517577/dd027a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117520000/117517600/117517577/0ca437fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117520000/117517600/117517577/60a86460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117517600/117517577/f0d778fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Hideaway on the Beach Central Kihei 10/10 Exceptional (2) "We really enjoyed this house! It had everything we needed and more! They provided beach chairs and umbrellas, all the kitchen necessities, and even a high chair and port-a-crib for the baby! It was clean and spacious. Host was been very efficient and friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristine D. CA $2,266 CA $4,165 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Kihei-Hotels-Oceanfront-Hideaway-On-The-Beach.h117517577.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12®ionId=553248621593965869&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248621593965869) ![](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 ![Sheraton Maui Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/22900/22894/w4000h2664x0y0-b7d636ba_y.jpg) ### Sheraton Maui Resort & Spa 10/10 Excellent "Very clean property and welcoming staff. We loved our stay!" [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![The Whaler Resort Kaanapali Beach](https://images.trvl-media.com/lodging/96000000/95040000/95034100/95034061/b85a7c13_y.jpg) ### The Whaler Resort Kaanapali Beach 10/10 Excellent "Unit was spacious, well stocked, clean, staff was great, beach views amazing" [](https://expedia.ca/Kaanapali-Hotels-The-Whaler-Resort-Kaanapali-Beach.h95034061.Hotel-Information) ![OUTRIGGER Kaanapali Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/11600/11554/82021c2d_y.jpg) ### OUTRIGGER Kaanapali Beach Resort 10/10 Excellent "Beautiful location. Staff was fantastic. View was stunning. Breakfast was good. Housekeeping was fabulous. " [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "The corner suite was absolutely gorgeous. " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![Maui Seaside Hotel](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg) ### Maui Seaside Hotel 10/10 Excellent "Room and pool updated. Comfortable and friendly staff. Good for short stay. Free shuttle to/from airport " [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg) ### Royal Lahaina Resort & Bungalows 10/10 Excellent "What a wonderful place to stay!! Staff was awesome really close to the beach and the trolley was a nice touch being able to ride to other resort areas. " [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![Maui Coast Hotel](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/ffbd6b5d_y.jpg) ### Maui Coast Hotel 10/10 Excellent "We had a wonderful one night stay! The staff was terrific, we loved the pool and the beautiful balcony!" [](https://expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.Hotel-Information) ![Maui Beach Hotel](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg) ### Maui Beach Hotel 10/10 Excellent "The staff was very kind and helpful. During check in the staff was very informative of where things were. " [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](https://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" [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ## Find out more about Upcountry Maui ## Upcountry Maui Vacation Homes information | Number of reviews | 1,820 | | --- | --- | | Accommodation | 179 Vacation Homes | | Lowest Price | CA $342 | | Highest Price | CA $4,165 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Maui](https://www.expedia.ca/5Star-Maui-Hotels.s50-0-d180073.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala Crater](https://www.expedia.ca/Haleakala-Crater-Hotels.0-l501684-0.Travel-Guide-Filter-Hotels) - [Hotels near Haleakala National Park](https://www.expedia.ca/Haleakala-National-Park-Hotels.0-l507525-0.Travel-Guide-Filter-Hotels) - 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