Title: Book the Best Hotels with POOL in Upcountry Maui in 2026 | 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) ![View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds. #AboveItAll](https://images.trvl-media.com/place/507525/451f5c7a-2ae1-4683-8787-8d1827405b60.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Project Forever # Find Hotels with a Pool in Upcountry Maui, HI from CA $379 - ![](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 availability on Upcountry Maui Hotels with a Pool Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-21&endDate=2025-12-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-22&endDate=2025-12-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621593965869&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upcountry Maui hotels with a pool ![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248443/1e4918bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248443/9ba6e1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248443/b290affc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness studio](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248443/92a88d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lumeria Maui Educational Retreat Center [](https://www.expedia.ca/Makawao-Hotels-Lumeria-Maui-Educational-Retreat-Center.h5248443.Hotel-Information) Makawao 8.6/10 Excellent (209) "The staff were kind and helpful. The rooms were comfortable and the property is gorgeous and well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah Catherine CA $601 CA $828 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Makawao-Hotels-Lumeria-Maui-Educational-Retreat-Center.h5248443.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.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) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/d58312bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) Makawao 10/10 Exceptional (71) "We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kari L. CA $2,201 CA $4,376 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/a4d29c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/30133290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/7d2e58bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royal Lahaina Resort & Bungalows [](https://www.expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) Lahaina 8.4/10 Very good (1576) "Excellent resort environment, Beautiful beach and nice staff. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) dewei CA $318 CA $451 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/fd9163f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/44c8cd74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/40492e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Kai Ocean View Ali i Suite | View from room](https://images.trvl-media.com/lodging/1000000/30000/28700/28645/88b76a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maui Coast Hotel [](https://www.expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.Hotel-Information) South Kihei 9.6/10 Exceptional (2336) "Always a great stay for business!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $313 CA $435 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Kihei-Hotels-Maui-Coast-Hotel.h28645.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/113000000/112740000/112737600/112737554/w3840h2556x0y3-56e27344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/113000000/112740000/112737600/112737554/w3837h2557x3y3-540cb919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/113000000/112740000/112737600/112737554/w3840h2556x0y4-772d2f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112740000/112737600/112737554/w3836h2557x4y3-056aecc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Maui North Shore [](https://www.expedia.ca/Kahului-Hotels-Hampton-Inn-Suites-Maui-North-Shore.h112737554.Hotel-Information) Kahului 9.0/10 Wonderful (164) "Very friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randall Kalani Apilando CA $466 CA $594 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Kahului-Hotels-Hampton-Inn-Suites-Maui-North-Shore.h112737554.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/32df3640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Ocean View, Tower (Makai Tower, Newly Renovated) | View from room](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/870234ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/5df916fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/dbb5bb4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maui Seaside Hotel [](https://www.expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) Kahului 9.0/10 Wonderful (1190) "Friendly staff; great location; island vibe" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janell CA $316 CA $407 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/ce2f0b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/2fcc9418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/96f5b87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maui Beach Hotel [](https://www.expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) Kahului 7.2/10 Good (1117) "Awesome staff awesome view couldn’t ask for more from this quaint cute hotel vibe!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey CA $292 CA $379 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/b61d1cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/04b763de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/167c62f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/6dafebb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Maui Kahului Airport [](https://www.expedia.ca/Kahului-Hotels-Courtyard-Maui-Kahului-Airport.h5087798.Hotel-Information) Kahului 9.0/10 Wonderful (1002) "Clean room,helpful and pleasant staff, good food in the Bistro, quiet, comfortable room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $503 CA $597 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Kahului-Hotels-Courtyard-Maui-Kahului-Airport.h5087798.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/85e14a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Penthouse, Kitchen, Garden View](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/0142f7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/b8bb8a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/f0f99626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kohea Kai Hotel Maui [](https://www.expedia.ca/Kihei-Hotels-Kohea-Kai-Hotel-Maui.h1439959.Hotel-Information) North Kihei 8.6/10 Excellent (882) "We loved our stay here! Perfect location, great room, and the staff is so friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emma CA $327 CA $429 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kihei-Hotels-Kohea-Kai-Hotel-Maui.h1439959.Hotel-Information) ![Outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3100/3001/3ff05126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3100/3001/cf12a18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/3100/3001/aef81e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/1000000/10000/3100/3001/7df1f408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Grand Vacations Club Maui Bay Villas [](https://www.expedia.ca/Kihei-Hotels-Maui-Bay-Villas-By-Hilton-Grand-Vacations.h3001.Hotel-Information) North Kihei 9.2/10 Wonderful (222) "Clean and well equipped room, helpful and friendly staff. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Asel CA $496 CA $637 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Kihei-Hotels-Maui-Bay-Villas-By-Hilton-Grand-Vacations.h3001.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=2026-01-04&endDate=2026-01-05®ionId=553248621593965869&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Upcountry Maui Hotel Reviews ![OUTRIGGER Kaanapali Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/11600/11554/82021c2d_y.jpg) ### OUTRIGGER Kaanapali Beach Resort 10/10 Excellent "Was an amazing resort " [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Hilton Vacation Club Ka'anapali Beach Maui](https://images.trvl-media.com/lodging/1000000/30000/23100/23042/7a9e8592_y.jpg) ### Hilton Vacation Club Ka'anapali Beach Maui 10/10 Excellent "The room was amazing, very clean " [](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.Hotel-Information) ![OUTRIGGER Honua Kai Resort & Spa](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/cc604c30_y.jpg) ### OUTRIGGER Honua Kai Resort & Spa 10/10 Excellent "Yes. Great stay as always " [](https://expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.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 "Great service" [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![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 "Mo" [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![The Ritz-Carlton Maui, Kapalua](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53_y.jpg) ### The Ritz-Carlton Maui, Kapalua 10/10 Excellent "Staff was courteous and very engaging." [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.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 "Room was amazing with the bungalow view. Breakfast was quick and easy and very good with an incredible view" [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![Maui Seaside Hotel](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg) ### Maui Seaside Hotel 10/10 Excellent "Outstanding " [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ![The Westin Maui Resort & Spa, Ka'anapali](https://images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg) ### The Westin Maui Resort & Spa, Ka'anapali 10/10 Excellent "A great stay, kind greetings and all kindness of hospitality! Was beautiful im all sense of views and great location to great restaurants, shopping, and most importantly the beach!🏖️ . A simple thank you for this stay and cant wait to come back! 🙏🌺" [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [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) - [Hotels & Resorts for Couples in Kaanapali ](https://www.expedia.ca/Kaanapali-Hotels-Couples-Resorts-Hotels.0-0-d800065-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Kaanapali ](https://www.expedia.ca/Kaanapali-Hotels-Hotel-With-Early-Check-In.0-0-d800065-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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