Title: Book the Best Hotels with POOL in Kaupo in 2025 | Expedia.ca [Hotels in Kaupo](https://expedia.ca/Kaupo-Hotels.d11826.Travel-Guide-Hotels)[Vacation Rentals in Kaupo](https://expedia.ca/Kaupo-Vacation-Rentals.d11826.Travel-Guide-VacationRentals)[Things to do in Kaupo](https://expedia.ca/Things-To-Do-In-Kaupo.d11826.Travel-Guide-Activities)[Kaupo Car Rentals](https://expedia.ca/Car-Rentals-In-Kaupo.d11826.Car-Rental-Guide)[Kaupo Vacation Packages](https://expedia.ca/Kaupo.d11826.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/412ef9807c8494de27c2c701b373deea.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tim & Nat ✈ # Find Hotels with a Pool in Kaupo, HI from CA $774 ![](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 Kaupo Hotels with a Pool Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=11826&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kaupo 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) ![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) ![Premier Suite, 1 King Bed, Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/1000/933/c9c38afc.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) ### Hana-Maui Resort, a Destination by Hyatt Residence Hana 9.2/10 Wonderful (1007) "Beautiful location, great ocean views, loved the food truck options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $593 CA $774 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hana-Hotels-Hana-Maui-Resort.h933.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/108000000/107420000/107413400/107413317/a7d7c739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107420000/107413400/107413317/832b5f9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/108000000/107420000/107413400/107413317/74e51233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107420000/107413400/107413317/e302ef64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 180 Degree Ocean View in Wailea! WE204 Wailea 10/10 Exceptional (2) "This was the first time my husband and I stayed in Wailea. We typically stay in Kaanapali and decided to give the other side of the island a chance. Everything about this home from location to ease of communication was beyond expectation. We loved every minute of our stay and we highly recommend this location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) claudia s. CA $273 CA $957 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Kihei-Hotels-180-Degree-Ocean-View-In-Wailea-WE204.h107413317.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/19000000/19000000/18992700/18992628/bee551dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18992700/18992628/83685ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/19000000/18992700/18992628/68548140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/19000000/18992700/18992628/7fddce93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting Wailea 9.8/10 Exceptional (184) "Great location and beautiful views, perfect spot to relax on Maui." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron S. CA $350 CA $884 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Kihei-Hotels-Spectacular-Ocean-View.h18992628.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) ![Exterior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/606a40d5.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) ![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 Makawao 10/10 Exceptional (70) "Amazing Property!! Host was very friendly and gracious with time for checking in and out. Our whole family wish we could have stayed longer. Perfect spot for all of our activities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie W. CA $2,231 CA $4,256 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/4d17dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Regional cuisine](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/ee7d62b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/887fcb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d4acdf82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Wailea, Relais & Chateaux - Adults Only Wailea 9.4/10 Exceptional (1002) "Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $1,195 CA $1,493 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96160000/96155400/96155312/88248f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/97000000/96160000/96155400/96155312/761e723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96160000/96155400/96155312/c81e72cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96160000/96155400/96155312/4e52e163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Remodel! Two King Suites & Huge Ocean Views! Close To Wailea Beaches Wailea 9.6/10 Exceptional (25) "All perfect in heaven. Mahalo" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jean philippe l. CA $624 CA $1,592 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Kihei-Hotels-Gorgeous-FULLY-REMODELED-Condo-With-Two-King-Suites-Panoramic-Ocean-Views.h96155312.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=2025-11-08&endDate=2025-11-09®ionId=11826&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Kaupo Hotel Reviews ![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 "Exceeded all expectations. And the staff was wonderful." [](https://expedia.ca/Hana-Hotels-Hana-Maui-Resort.h933.Hotel-Information) ![Hotel Wailea, Relais & Chateaux - Adults Only](//images.trvl-media.com/lodging/1000000/90000/85500/85412/51e44f40_y.jpg) ### Hotel Wailea, Relais & Chateaux - Adults Only 10/10 Excellent "This place. So special. The crème de la creme. 5+stars. Cannot WAIT to go back!" [](https://expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) ![Wailea Ekolu - CoralTree Residence Collection](//images.trvl-media.com/lodging/1000000/890000/882800/882766/65046eb5_y.jpg) ### Wailea Ekolu - CoralTree Residence Collection 10/10 Excellent "It’s a great place to Stay for the family vacation." [](https://expedia.ca/Kihei-Hotels-Wailea-Ekolu-Village.h882766.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Kaupo? > [Hana-Maui Resort, a Destination by Hyatt Residence](https://www.expedia.ca/Hana-Hotels-Hana-Maui-Resort.h933.Hotel-Information): Features a full-service spa, 2 outdoor pools, and a sauna. [Hotel Wailea, Relais & Chateaux - Adults Only](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information): Resort located near Wailea Beach. Offers 3 restaurants, an outdoor pool, and spa services. [Oceanview Condo in Hana-Let the ocean lull you to sleep](https://www.expedia.ca/Hana-Hotels-Oceanview-Condo-In-Hana-Let-The-Ocean-Lull-You-To-Sleep.h71595183.Hotel-Information): Condo located near Wailea Beach. Offers complimentary wired internet access, 2 outdoor pools, and free self parking. [Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.](https://www.expedia.ca/Makawao-Hotels-Charming-Bed-Breakfast-On-The-Slopes-Of-Haleakala-With-AC.h109553718.Hotel-Information): Features complimentary wireless internet access, a pool, and kitchens. [Wailea Ekolu - CoralTree Residence Collection](https://www.expedia.ca/Kihei-Hotels-Wailea-Ekolu-Village.h882766.Hotel-Information): Condo located near Wailea Beach. Offers complimentary wireless internet access, a communal pool, and kitchens. ### What is there to see and do in Kaupo? > Spend some time experiencing the great outdoors at Haleakala National Park. Discover sights such as Bamboo Forest, Wailua Falls, and Haleakalā Visitor Center during your stay. ### When is the best time to book a hotel with a pool in Kaupo? > Taking into account the local weather in Kaupo 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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