Title: Book the Best Hotels with POOL in Kaanapali Hillside in 2025 | Expedia.ca [Kaanapali Hillside Travel Guide](https://expedia.ca/Kaanapali-Hillside.dx553248635976471188)[Hotels in Kaanapali Hillside](https://expedia.ca/Kaanapali-Hillside-Hotels.d553248635976471188.Travel-Guide-Hotels)[Vacation Rentals in Kaanapali Hillside](https://expedia.ca/Kaanapali-Hillside-Vacation-Rentals.d553248635976471188.Travel-Guide-VacationRentals)[Kaanapali Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Kaanapali-Hillside.d553248635976471188.Car-Rental-Guide)[Kaanapali Hillside Vacation Packages](https://expedia.ca/Kaanapali-Hillside.d553248635976471188.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Kaanapali Hillside, HI from CA $245 ![](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 Kaanapali Hillside Hotels with a Pool Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976471188&startDate=2025-10-22&endDate=2025-10-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976471188&startDate=2025-10-23&endDate=2025-10-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976471188&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471188&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kaanapali Hillside Hotels with a Pool ![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) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/d56f083f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/627bd007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kohea Kai Hotel Maui North Kihei 8.6/10 Excellent (853) "The beach view was incredible and the food nearby was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex CA $244 CA $329 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Kihei-Hotels-Kohea-Kai-Hotel-Maui.h1439959.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) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/743611fa.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/f844108d.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/f5a81ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royal Lahaina Resort & Bungalows Lahaina 8.4/10 Very good (1497) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $254 CA $374 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![Outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Garden View, Tower (Makai Tower, Newly Renovated)](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/06e5e7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/68fd6782.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) ### Maui Seaside Hotel Kahului 9.0/10 Wonderful (1173) "It was a great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mona CA $296 CA $382 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.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) ![On the beach](https://images.trvl-media.com/lodging/113000000/112740000/112737600/112737554/f790755c.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) ![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 Kahului 9.2/10 Wonderful (121) "Amazing staff and amazing stay!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jeremiah CA $449 CA $571 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Kahului-Hotels-Hampton-Inn-Suites-Maui-North-Shore.h112737554.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/3c9723ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/63ca0e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/92e297af.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) ### Maui Beach Hotel Kahului 7.2/10 Good (1099) "Loved the local feel, clean, friendly staff and ocean front. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liana CA $260 CA $340 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/cc604c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 3 Bedrooms, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/fa899b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/7880dbd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/3000000/2750000/2740200/2740153/0edd56a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OUTRIGGER Honua Kai Resort & Spa Lahaina 8.8/10 Excellent (2854) "Resort was beautiful and family friendly. Definitely will stay here again with the rest of the family" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alisha CA $384 CA $1,096 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Lahaina-Hotels-Honua-Kai-Resort-Spa.h2740153.Hotel-Information) ![Beach nearby, white sand, beach towels](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/60365101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/a901f03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio, Garden View | Garden view](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/cd4c5baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio, Garden View](https://images.trvl-media.com/lodging/104000000/103030000/103028100/103028003/24289f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Napili Village Hotel Lahaina 9.0/10 Wonderful (119) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Destiny CA $208 CA $245 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Kapalua-Hotels-Napili-Village-Hotel.h103028003.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/6389d34f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/77cc46dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/ebc7e42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18800/18735/0d5ab47f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aston Maui Kaanapali Villas Lahaina 8.8/10 Excellent (2475) "Beautiful quiet property on the beach with dining options and shopping a short walk or shuttle ride away" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gilda CA $318 CA $498 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Lahaina-Hotels-Aston-Maui-Kaanapali-Villas.h18735.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) ![Reception](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/0c89242a.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) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/4ceca7d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Maui Kahului Airport Kahului 9.0/10 Wonderful (1004) "Great location and clean property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leinell CA $492 CA $581 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Kahului-Hotels-Courtyard-Maui-Kahului-Airport.h5087798.Hotel-Information) ![Villa, 2 Bedrooms, Oceanfront (Bay 25G2 Gold 2.5 Bath) | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/db3c4dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Ocean Front (Bay 18G3, Gold, 1.5 Bath) | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/98889b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Oceanfront (Bay 26G2 Gold ,1Bath) | Private kitchen](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/cdef340e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Oceanfront (Bay 36B3 Gold ,1Bath)](https://images.trvl-media.com/lodging/1000000/30000/22500/22419/84e6455b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kapalua Villas Maui Lahaina 8.8/10 Excellent (955) "Gorgeous property, the staff, beach, hiking close by, restaurants in area all were great. Room was spotless and we were able to check in early." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arturo CA $312 CA $1,110 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Lahaina-Hotels-Kapalua-Villas-Maui.h22419.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=2025-11-06&endDate=2025-11-07®ionId=553248635976471188&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Kaanapali Hillside Hotel Reviews ![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 "Clean room, polite and friendly staff, grounds well maintained " [](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.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 "All was great" [](https://expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information) ![Aston Kaanapali Shores](//images.trvl-media.com/lodging/1000000/10000/1300/1284/cb6fb615_y.jpg) ### Aston Kaanapali Shores 10/10 Excellent "The Air Conditioner was not working for a night. We called and got it fixed quickly. AC stopped when we open the balcony doors. That was a bit inconvenient. " [](https://expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information) ![Maui Beach Hotel](//images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg) ### Maui Beach Hotel 10/10 Excellent "Great staff" [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![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 property and near beach" [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.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 "My favorite hotel with an ocean front view. Can't be beat." [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![Maui Seaside Hotel](//images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg) ### Maui Seaside Hotel 10/10 Excellent "We had an upgraded room which was fantastic. Staff was very nice. However, the restaurant onsite is terrible. I wish I had known Burger King was across the street I would have gone there. " [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.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 "Beautiful resort, was pleasantly surprised by free valet on the first night. Ate at the poolside bar for dinner and was impressed with the gourmet quality of the salad I had. Beach access was excellent! " [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![Hyatt Regency Maui Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19300/19207/3102d1ec_y.jpg) ### Hyatt Regency Maui Resort & Spa 10/10 Excellent "Excellent cleanliness and everything was fantastic " [](https://expedia.ca/Lahaina-Hotels-Hyatt-Regency-Maui.h19207.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Kaanapali Hillside? > [Aston Kaanapali Shores](https://www.expedia.ca/Lahaina-Hotels-Aston-Kaanapali-Shores.h1284.Hotel-Information): Aparthotel located near Kaanapali Beach. Features a full-service spa, 2 outdoor pools, and 2 hot tubs. [Royal Lahaina Resort & Bungalows](https://www.expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information): Hotel, 8-minute walk from Kaanapali Beach. Offers a full-service spa, 2 outdoor pools, and 2 bars. [The Ritz-Carlton Maui, Kapalua](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information): Resort located near Napili Bay. Provides 3 outdoor pools, a children's pool, and 6 restaurants. [The Westin Maui Resort & Spa, Ka'anapali](https://www.expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information): Hotel steps from Whalers Village. Features 2 restaurants, 3 outdoor pools, and a full-service spa. [OUTRIGGER Kaanapali Beach Resort](https://www.expedia.ca/Lahaina-Hotels-OUTRIGGER-Kaanapali-Beach-Resort.h11554.Hotel-Information): Resort, 6-minute walk from Kaanapali Beach. Offers cabanas (surcharge), an outdoor pool, and a snack bar/deli. ### What is there to see and do in Kaanapali Hillside? > Explore places like Kaanapali Beach while you're in the area. Make a point to visit attractions like Kahana Beach and Maui Nui Botanical Gardens. ### When is the best time to book a hotel with a pool in Kaanapali Hillside? > Taking into account the local weather in Kaanapali Hillside can help you maximize your time at the pool during your trip. The hottest months are usually September and August with an average temp of 78°F, while the coldest months are February and March with an average of 73°F. 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