Title: Book the Best Hotels with POOL in Kailua in 2025 | Expedia.ca [Hotels in Kailua](https://expedia.ca/Kailua-Hotels.d11832.Travel-Guide-Hotels)[Vacation Rentals in Kailua](https://expedia.ca/Kailua-Vacation-Rentals.d11832.Travel-Guide-VacationRentals)[Kailua Car Rentals](https://expedia.ca/Car-Rentals-In-Kailua.d11832.Car-Rental-Guide)[Kailua Vacation Packages](https://expedia.ca/Kailua.d11832.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/a42fa477d95ebfbccef32c86caac5f76.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Kailua, HI from CA $361 ![](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 Kailua Hotels with a Pool Tonight [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=11832&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=11832&startDate=2025-10-10&endDate=2025-10-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=11832&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=11832&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kailua Hotels with a Pool ![2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/1000/933/f8d26b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Partial Ocean View](https://images.trvl-media.com/lodging/1000000/10000/1000/933/c688bfe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow, 1 King Bed, Ocean View](https://images.trvl-media.com/lodging/1000000/10000/1000/933/2eaf6209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, free beach shuttle](https://images.trvl-media.com/lodging/1000000/10000/1000/933/165b99af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hana-Maui Resort, a Destination by Hyatt Residence Hana 9.0/10 Wonderful (1001) "The staff was super friendly. " CA $594 CA $787 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hana-Hotels-Hana-Maui-Resort.h933.Hotel-Information) ![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/b290affc.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) ![Lobby](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248443/fac4b41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lumeria Maui Educational Retreat Center Makawao 8.6/10 Excellent (208) "Could not be happier. The staff were professional and accommodating. Excellent yoga sessions and lovely, relaxing massage services. The grounds and pool are absolutely stunning. Nice relaxing vacation. The breakfast is top notch. Highly recommend Lumeria. " CA $434 CA $628 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Makawao-Hotels-Lumeria-Maui-Educational-Retreat-Center.h5248443.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) ![Lobby](https://images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/1e9e3352.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) ### Courtyard Maui Kahului Airport Kahului 9.0/10 Wonderful (1001) "Great location and clean property. " CA $494 CA $582 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Kahului-Hotels-Courtyard-Maui-Kahului-Airport.h5087798.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/89e2225f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/265e1013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/79fb7e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/a9c993e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles! North Kihei 9.8/10 Exceptional (293) "Locally convenient, price was right for the location, property management was on top of things and made sure that we were well taken car of. " CA $140 CA $547 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18978176.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/af4b8884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/291eb0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/w1170h877x0y5-51fd63d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18990000/18980100/18980054/96d0f8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles! North Kihei 9.8/10 Exceptional (258) "Very clean, close to beaches and town. The host was also great with communication and recommendations. Highly recommend! " CA $138 CA $535 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18980054.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630857/fea1bb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630857/3c3cf368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, streaming services](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630857/b9c24671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630857/w1019h683x3y0-0a510844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View! North Kihei 10/10 Exceptional (26) "Great location and beaches around! Tracy was great with communication and letting us know all the the ins and the outs of the island. " CA $140 CA $524 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Kihei-Hotels-This-Remodeled-Condo-Earned-Best-In-Kihei-4-Times-And-1-In-Maui-Ocean-View.h83630857.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/50000000/49020000/49010700/49010643/132412af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49020000/49010700/49010643/f6eae4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49020000/49010700/49010643/229f8380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49020000/49010700/49010643/051693ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets Central Kihei 10/10 Exceptional (188) "Host was accomodating of an early check in, unit was clean and well stocked. Excellent location!" CA $208 CA $627 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Kihei-Hotels-Oceanfront.h49010643.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119870000/119867800/119867771/3f40313f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/120000000/119870000/119867800/119867771/fe4b78ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Condo, Balcony, Ocean View | Living area](https://images.trvl-media.com/lodging/120000000/119870000/119867800/119867771/6cd770cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Condo, Balcony, Ocean View | Extra beds](https://images.trvl-media.com/lodging/120000000/119870000/119867800/119867771/f512763b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kalama Residence South Kihei CA $221 CA $691 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Kihei-Hotels-The-Kalama-Residence.h119867771.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) ![Suite, 1 King Bed, Kitchen, Pool View | Private kitchen](https://images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/05531b97.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 (849) "The beach view was incredible and the food nearby was great!" CA $271 CA $361 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kihei-Hotels-Kohea-Kai-Hotel-Maui.h1439959.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22210000/22203300/22203222/99650e70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/23000000/22210000/22203300/22203222/18593751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/23000000/22210000/22203300/22203222/7b3b2015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22210000/22203300/22203222/fbadded2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Second Floor Oceanview with Gorgeous Sunsets Central Kihei 9.0/10 Wonderful (27) "Great location! Can hear the waves at night. Walk to groceries and restaurants and the beach is right out front. Can watch the whales from the lanai, walk on the beach and soak up the sun. Doesn't get any better than that." CA $160 CA $910 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Kihei-Hotels-Second-Floor-Oceanview-With-Gorgeous-Sunsets.h22203222.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25®ionId=11832&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Kailua Hotel Reviews ![Maui Beach Vacation Club](//images.trvl-media.com/lodging/1000000/10000/2500/2457/618976ae_y.jpg) ### Maui Beach Vacation Club 10/10 Excellent "Room was quiet, no ac but the breeze came through very nice. Comfortable and convenient location. " [](https://expedia.ca/Kihei-Hotels-Maui-Beach-Vacation-Club.h2457.Hotel-Information) ![Maui Seaside Hotel](//images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg) ### Maui Seaside Hotel 10/10 Excellent "Nice little hotel close to airport. Staff were friendly and room was clean. Nice view of harbour." [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ![Maui Schooner Resort](//images.trvl-media.com/lodging/1000000/890000/880600/880544/074bc0c8_y.jpg) ### Maui Schooner Resort 10/10 Excellent "Property was well kept, quiet and centrally located" [](https://expedia.ca/Kihei-Hotels-Maui-Schooner-Resort.h880544.Hotel-Information) ![Hana-Maui Resort, a Destination by Hyatt Residence](//images.trvl-media.com/lodging/1000000/10000/1000/933/f8d26b60_y.jpg) ### Hana-Maui Resort, a Destination by Hyatt Residence 10/10 Excellent "Was the best place i have ever stayed. Hands down. The treatment and property were 5 star from minute 1. I couldnt be more impressed with the staff and the accomodations were fantastic too. Thanks for a great couple of days in paradise" [](https://expedia.ca/Hana-Hotels-Hana-Maui-Resort.h933.Hotel-Information) ![Sugar Beach Resort](//images.trvl-media.com/lodging/3000000/2840000/2833100/2833007/7a703a44_y.jpg) ### Sugar Beach Resort 10/10 Excellent "We have a great time and the accommodations were great. Thank you." [](https://expedia.ca/Kihei-Hotels-Sugar-Beach-Resort-By-Vacasa.h2833007.Hotel-Information) ![Maui Beach Hotel](//images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg) ### Maui Beach Hotel 10/10 Excellent "This is a phony questioner. It locked me in as excellent. Which i would have marked as awful. I wiii get the word out" [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![Kohea Kai Hotel Maui](//images.trvl-media.com/lodging/2000000/1440000/1440000/1439959/d56f083f_y.jpg) ### Kohea Kai Hotel Maui 10/10 Excellent "The woman at the front desk was incredibly welcoming and helpful…and seemingly always there. The hotel was a short walk across a busy street from the beach…and a nice park area a little farther south. Hotel provided chairs, umbrellas, coolers and beach towels. The suite was super comfortable and cooled off nicely by the time we arrived. A/C worked great. Bathroom came with all of the toiletries needed. Kitchen had a nice assortment of dishes and cooking items. We had a in room coffee pot but walked over to the office each day for coffee, tea, filtered water and ice. Patio outside our room was a nice morning coffee and evening wind-down spot. The garden was serene and beautiful. The small pool and hot tub were well-maintained. Free parking was a nice bonus as was being close to a bus stop before we got our car. Thanks for a great stay for a great price! " [](https://expedia.ca/Kihei-Hotels-Kohea-Kai-Hotel-Maui.h1439959.Hotel-Information) ![Paia Inn](//images.trvl-media.com/lodging/3000000/2280000/2273000/2272947/5ff4e9ec_y.jpg) ### Paia Inn 10/10 Excellent "I liked the privacy and also the decor" [](https://expedia.ca/Paia-Hotels-Paia-Inn.h2272947.Hotel-Information) ![Courtyard Maui Kahului Airport](//images.trvl-media.com/lodging/6000000/5090000/5087800/5087798/04b763de_y.jpg) ### Courtyard Maui Kahului Airport 10/10 Excellent "Stream lined processes. Loved the hot pool. Too early to give a bad rap." [](https://expedia.ca/Kahului-Hotels-Courtyard-Maui-Kahului-Airport.h5087798.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Kailua? > [Maui Seaside Hotel](https://www.expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information): Features complimentary wireless internet access, an outdoor pool, and flat-screen televisions. [Hilton Grand Vacations Club Maui Bay Villas](https://www.expedia.ca/Kihei-Hotels-Maui-Bay-Villas-By-Hilton-Grand-Vacations.h3001.Hotel-Information): Offers a children's pool, an outdoor pool, and a snack bar/deli. [Maui Beach Hotel](https://www.expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information): Provides a 24-hour fitness center, an outdoor pool, and LED televisions. [Hampton Inn & Suites Maui North Shore](https://www.expedia.ca/Kahului-Hotels-Hampton-Inn-Suites-Maui-North-Shore.h112737554.Hotel-Information): Features buffet, an outdoor pool, and complimentary wireless internet access. [Yonegan Central Maui Getaways](https://www.expedia.ca/Wailuku-Hotels-Yonegan-Central-Maui-Getaways.h117929085.Hotel-Information): Features free self parking, an outdoor pool, and complimentary wireless internet access. ### What is there to see and do in Kailua? > Enjoy a stroll along the shore at Hoʻokipa Beach Park and Kuau Bay Beach. Discover sights such as Twin Falls, Garden of Eden Arboretum, and Maui Garden Of Eden - Botanical Gardens & Arboretum during your stay. ### When is the best time to book a hotel with a pool in Kailua? > Taking into account the local weather in Kailua is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and September with an average temp of 75°F, while the coldest months are March and February with an average of 71°F. 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