Title: Book the Best Hotels with POOL in Wailea in 2025 | Expedia.ca [Wailea Travel Guide](https://expedia.ca/Kihei-Wailea.dx7739)[Vacation Rentals in Kihei](https://expedia.ca/Kihei-Vacation-Rentals.d9304.Travel-Guide-VacationRentals)[Flights to Kihei](https://expedia.ca/Cheap-Flights-To-Kihei.d9304.Travel-Guide-Flights)[Things to do in Kihei](https://expedia.ca/Things-To-Do-In-Kihei.d9304.Travel-Guide-Activities)[Wailea Car Rentals](https://expedia.ca/Car-Rentals-In-Wailea.d7739.Car-Rental-Guide)[Wailea Vacations](https://expedia.ca/Wailea.d7739.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/37000/37443-Molokini.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Wailea, HI from CA $640 - ![](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 Wailea Hotels with a Pool Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-11-04&endDate=2025-11-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-11-05&endDate=2025-11-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wailea Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119850000/119846200/119846199/7c53e9a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119850000/119846200/119846199/09bc13c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/120000000/119850000/119846200/119846199/bf4df0a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Balcony, Pool View | Living area](https://images.trvl-media.com/lodging/120000000/119850000/119846200/119846199/8dbf1cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Champions Wailea CA $178 CA $812 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Kihei-Hotels-Grand-Champions.h119846199.Hotel-Information) ![4 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/b323b293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/62e684af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, Ground Floor (Sundeck)](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/78cfcb33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Balcony, Oceanfront](https://images.trvl-media.com/lodging/1000000/30000/20400/20303/b9ee0223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wailea Beach Resort - Marriott, Maui Wailea 9.2/10 Wonderful (1000) "Great location and very family friendly. Would recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dasia CA $742 CA $970 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Kihei-Hotels-Wailea-Beach-Resort-Marriott.h20303.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/c0b8dfb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/03d12ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, swim-up bar, poolside bar](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/eb7843a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/29664a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui Villa Experience Wailea 9.8/10 Exceptional (6) "Good property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Itzamnan CA $3,358 CA $4,044 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui-Villa-Experience.h37220226.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/58000000/57340000/57338800/57338761/3541c3db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/58000000/57340000/57338800/57338761/a0c88731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/58000000/57340000/57338800/57338761/da63d145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/58000000/57340000/57338800/57338761/8bfd0c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel by Marriott Maui Wailea Wailea 9.2/10 Wonderful (181) "Service from staff was amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ADAM CA $513 CA $640 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Kihei-Hotels-AC-Hotel-By-Marriott-Maui-Wailea.h57338761.Hotel-Information) ![Outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/13000000/12550000/12541900/12541875/c029e92e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/13000000/12550000/12541900/12541875/dc8d403b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12550000/12541900/12541875/6de86580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12550000/12541900/12541875/e8fce229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Maui Wailea Wailea 9.2/10 Wonderful (974) "We had a great stay in Wailea. We were close enough to the beaches without having the chaos of so many tourists. Room was clean, breakfast was a great bonus and staff was friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joey CA $561 CA $662 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Kihei-Hotels-Residence-Inn-By-Marriott-Maui-Wailea.h12541875.Hotel-Information) ![9 outdoor pools, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/8788f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/23013212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3837h2557x3y3-5ebfbeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Wailea Maui, A Waldorf Astoria Resort Wailea 8.8/10 Excellent (1017) "A step down from the Four Seasons next door, but it was an ok stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) EMANUEL CA $814 CA $1,051 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![Club Ocean Front One Bedroom Suite](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Maile Three-Bedroom Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/2cdd56af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/a0a6da1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/f9c45622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Maui at Wailea Wailea 9.6/10 Exceptional (1000) "Wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xianjun CA $1,061 CA $1,252 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139027/a9e40bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139027/8432f5b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139027/7c7cd70a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139027/03495293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ekahi Ocean View Escape and close to beach (21F) Wailea 9.8/10 Exceptional (62) "The unit is exactly as advertise, great location clean and simple." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $342 CA $1,280 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Kihei-Hotels-Beautifully-Remodeled-Ocean-View-Wailea-Condo-Walking-Distance-To-Beach.h34139027.Hotel-Information) ![5 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/487d8e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/7fac11ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/22480b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, 2 poolside bars](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/a723f933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Andaz Maui at Wailea Resort - a concept by Hyatt Wailea 9.2/10 Wonderful (1000) "Everything was great except food choices at their restaurants were limited and cleaning service was crazy loud." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $1,018 CA $1,284 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Kihei-Hotels-Andaz-Maui-At-Wailea-Resort-A-Concept-By-Hyatt.h2552.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/73000000/72980000/72978100/72978030/aacb86c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/73000000/72980000/72978100/72978030/3a2cb3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/73000000/72980000/72978100/72978030/5bfec023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72980000/72978100/72978030/002778fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wailea Luxury Retreat | Walk to Beach & Shops Wailea 9.2/10 Wonderful (7) "Perfect location for us to stay here. 5 mins walk to a mall, 3 mins to a golf course. Very comfortable to stay in a room. Wish to come back again.Mahalo" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) A0321A CA $148 CA $770 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Kihei-Hotels-Wailea-Luxury-Retreat-Walk-To-Beach-Shops.h72978030.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=2025-11-19&endDate=2025-11-20®ionId=7739&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Wailea | Less expensive | More expensive | This month | Next month | | --- | --- | --- | --- | | September | July | CA $520 | CA $582 | | Month | Price | | --- | --- | | January | CA $698 | | February | CA $638 | | March | CA $641 | | April | CA $501 | | May | CA $513 | | June | CA $545 | | July | CA $1,020 | | August | CA $756 | | September | CA $420 | | October | CA $957 | | November | CA $520 | | December | CA $582 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Wailea. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Wailea Hotel Reviews ![Grand Wailea Maui, A Waldorf Astoria Resort](//images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "We spent 1 day of our trip to Maui at the Grand Wailea to enjoy the pools before we left the island. This was our 4th time at Grand Wailea - and it was amazing again. There was a bit of concern with my initial booking that I tried to get corrected by phone before arrival, but Gilbert at the front desk was super reassuring and got us all sorted! We had a wonderful stay! Wayne at the swim-up bar was super nice, and we all loved the aquarium bar at Humahuma - definitely another highlight! " [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![Fairmont Kea Lani Maui](//images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "All of the above. Staff was extremely friendly and helpful. Housekeeping did a wonderful job with up keep in our room. To bringing water at night to our room, folding down our beds and having our slippers waiting. Always restocking the room. Our room view was breathtaking. Definitely would return " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![Wailea Beach Resort - Marriott, Maui](//images.trvl-media.com/lodging/1000000/30000/20400/20303/b323b293_y.jpg) ### Wailea Beach Resort - Marriott, Maui 10/10 Excellent "Really enjoyed our week here, nice room and extremely helpful and attentive staff. Location is great. " [](https://expedia.ca/Kihei-Hotels-Wailea-Beach-Resort-Marriott.h20303.Hotel-Information) ![Residence Inn by Marriott Maui Wailea](//images.trvl-media.com/lodging/13000000/12550000/12541900/12541875/c029e92e_y.jpg) ### Residence Inn by Marriott Maui Wailea 10/10 Excellent "Clean room, nice kitchen, good breakfast, very pleasant staff" [](https://expedia.ca/Kihei-Hotels-Residence-Inn-By-Marriott-Maui-Wailea.h12541875.Hotel-Information) ![Four Seasons Resort Maui at Wailea](//images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg) ### Four Seasons Resort Maui at Wailea 10/10 Excellent "Offered turn down service; the staff went above any beyond to ensure that we were comfortable. " [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![Wailea Grand Champions - CoralTree Residence Collection](//images.trvl-media.com/lodging/2000000/1210000/1202300/1202208/2ced1177_y.jpg) ### Wailea Grand Champions - CoralTree Residence Collection 10/10 Excellent "Clean room and nice decoration. Close to tennis club" [](https://expedia.ca/Kihei-Hotels-Wailea-Grand-Champions-Villas.h1202208.Hotel-Information) ![Wailea Beach Villas](//images.trvl-media.com/lodging/2000000/1440000/1437400/1437349/772d8e26_y.jpg) ### Wailea Beach Villas 10/10 Excellent "This spot is perfecto!" [](https://expedia.ca/Kihei-Hotels-Wailea-Beach-Villas.h1437349.Hotel-Information) ![Andaz Maui at Wailea Resort - a concept by Hyatt](//images.trvl-media.com/lodging/1000000/10000/2600/2552/487d8e2d_y.jpg) ### Andaz Maui at Wailea Resort - a concept by Hyatt 10/10 Excellent "This place is not for the average traveller. Plan on a large budget. The breakfast buffet for two with one mimosa each ran roughly $160 after tip. Dinner for two was a little over $400, after tip. The Luao for two was around $850. It was our 10-year anniversary, and I was well prepared and fully expected the expense. To me, it was worth it, and I would definitely come back again. Andaz has a very nice selection of swimming pools; there's even one just for grown-ups. The staff was always helpful, and a cocktail was always nearby. There's also plenty to keep you busy around the hotel. We did a snorkel tour and a dinner cruise. Both were incredible." [](https://expedia.ca/Kihei-Hotels-Andaz-Maui-At-Wailea-Resort-A-Concept-By-Hyatt.h2552.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) ## Frequently asked questions ### What are some accommodations with pools in Wailea? > [Grand Wailea Maui, A Waldorf Astoria Resort](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information): Resort, 9-minute walk from Wailea Beach. Features 9 outdoor pools, a children's pool, and a lazy river. [Wailea Beach Resort - Marriott, Maui](https://www.expedia.ca/Kihei-Hotels-Wailea-Beach-Resort-Marriott.h20303.Hotel-Information): Resort, 10-minute walk from Wailea Beach. Offers 4 outdoor pools, a children's pool, and 4 restaurants. [Andaz Maui at Wailea Resort - a concept by Hyatt](https://www.expedia.ca/Kihei-Hotels-Andaz-Maui-At-Wailea-Resort-A-Concept-By-Hyatt.h2552.Hotel-Information): Resort located near Wailea Beach. Provides 4 restaurants, 5 outdoor pools, and 2 pool bars. [Four Seasons Resort Maui at Wailea](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information): Resort, 6-minute walk from Wailea Beach. Features 3 outdoor pools, a children's pool, and 3 restaurants. [Fairmont Kea Lani Maui](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information): Resort, 11-minute walk from Wailea Beach. Offers 3 outdoor pools, a children's pool, and 6 restaurants. ### What is there to see and do in Wailea? > Explore places like Wailea Beach while you're in Wailea. Surround yourself with nature at Ulua Beach and Mokapu Beach. Visitors to Wailea speak highly of the natural attractions, including the beautiful beaches. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in South Maui](https://www.expedia.ca/3Star-South-Maui-Hotels.s30-0-d553248635975748717.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Halama Street](https://www.expedia.ca/Halama-Street-Kihei-Hotels-Cheap-Hotels.0-n553248635976471922-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Halama Street](https://www.expedia.ca/Halama-Street-Kihei-Hotels-Oceanfront-Hotels.0-n553248635976471922-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Halama Street](https://www.expedia.ca/Halama-Street-Kihei-Hotels-Spa-Hotel.0-n553248635976471922-0-tSpaHotel.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) - 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