Title: Book the Best HISTORIC Hotels 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 Historic Hotels in Wailea, HI from CA $429 ![](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 Historic Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wailea Historic Hotels ![Outdoor pool](https://images.trvl-media.com/lodging/32000000/31950000/31949200/31949120/9db2dd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31950000/31949200/31949120/648d2dd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31950000/31949200/31949120/e1562478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31950000/31949200/31949120/ee62f361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all! Wailea 10/10 Exceptional (57) "Great place and attentive owners" CA $537 CA $1,368 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Kihei-Hotels-1206-The-Palms-Wailea-Owner-Direct-Car-Available-The-Reviews-Say-It-All.h31949120.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34120000/34112200/34112190/f5491133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34120000/34112200/34112190/6e65b62f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34120000/34112200/34112190/93a9ff43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34120000/34112200/34112190/9b4a350b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views Wailea 9.8/10 Exceptional (59) "Good location. Amenities were adequate." CA $474 CA $1,237 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Kihei-Hotels-Sale-Gorgeous-3BR-2BA-Villa-In-Wailea.h34112190.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/w1675h1055x0y0-6392a616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/2ccbc532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/44ed2965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/9285d001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embark on a journey through Maui with Aloha Glamp Haiku-Pauwela 9.6/10 Exceptional (38) "He had everything for our camping, great experience " CA $182 CA $429 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Haiku-Hotels-Embark-On-A-Journey-Through-Maui-With-Aloha-Glamp.h27441539.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399140/b83b9690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399140/0bf26417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399140/215f5bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399140/26fd27e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paia Inn - 3 Bedroom Ocean Front Beach House Paia 10/10 Exceptional (1) "This is a beautiful property in an absolutely amazing location. We love love LOVED Paia - it is away from the more touristy areas of Maui, has great shops and restaurants, and it was so incredible to be directly on the beach while also being smack in the middle of town. When I booked, I did not realize that this house is part of a hotel, which made it a bit difficult to find at first, but it turned out to be great because we had the best of both worlds - our own house/space but with the... CA $2,385 CA $3,104 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Paia-Hotels-Paia-Inn-3-Bedroom-Ocean-Front-Beach-House.h64399140.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41540000/41534600/41534563/c8c5508b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/42000000/41540000/41534600/41534563/28d5f716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41540000/41534600/41534563/0f082a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41540000/41534600/41534563/cfe209de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI Central Kihei 9.2/10 Wonderful (20) "Nice place would stay there again. Close to beach" CA $125 CA $758 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Kihei-Hotels-200ft-From-The-Beach-Restaurants-King-Twin-Beds-Pool-WIFI.h41534563.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/19000000/18993500/18993493/f530e78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/19000000/18993500/18993493/16a19c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/19000000/18993500/18993493/2d457516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video-game console, DVD player, books](https://images.trvl-media.com/lodging/19000000/19000000/18993500/18993493/ab35817d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental South Kihei 9.6/10 Exceptional (47) "Good location near beach with AC in each room, many beds were good for a larger group." CA $279 CA $740 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Kihei-Hotels-Pacific-Shores-2bd-2bth-Kihei-MAUI-Condo-Kamaole-Beach-HAWAII-Vacation-Rental.h18993493.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) ![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/a9c993e8.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) ### 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles! North Kihei 9.8/10 Exceptional (294) "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 $550 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18978176.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/72000000/71400000/71390300/71390255/3d2b07a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71400000/71390300/71390255/fcb86949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71400000/71390300/71390255/71439470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71400000/71390300/71390255/953a6332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*25% Off-Steps to Beach-AC in Every Room-Remodeled South Kihei 10/10 Exceptional (2) "If I could give this property a 10 star review I would. This great place had all we needed to have a fantastic stay in Maui. It was a comfortable stay for four adults. It was well stocked for all of our cooking needs and also had everything we needed for our trips to the beach. I would definitely recommend this property for anyone. We will make it a stop on our next trip to Maui." CA $211 CA $832 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Kihei-Hotels-25-Off-Steps-To-Beach-AC-In-Every-Room-Remodeled.h71390255.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/33000000/32999500/32999423/380917d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/33000000/33000000/32999500/32999423/03065965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/33000000/32999500/32999423/3dd81efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/33000000/32999500/32999423/3d9b83c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🤙 Nov-Dec-Jan SPECIALS 🏝️ at the classic LIVE ALOHA SUITE North Kihei 10/10 Exceptional (136) "We stayed here for 3 nights. Location was great, view was breathtaking!" CA $336 CA $903 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Kihei-Hotels-Welcome-Back-To-The-Clean-Live-Aloha-Suite.h32999423.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18991900/18991875/w1170h877x0y2-81f58d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/19000000/18991900/18991875/24d26a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18991900/18991875/8d132e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/19000000/19000000/18991900/18991875/67a48cc1.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 9.6/10 Exceptional (285) "Had a great experience here it was close to everything in town and near alot of cool beaches! Would definitely return" CA $139 CA $549 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18991875.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=2025-10-29&endDate=2025-10-30®ionId=7739&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Wailea | Less expensive | More expensive | Next month | | --- | --- | --- | | August | February | CA $457 | | Month | Price | | --- | --- | | January | CA $677 | | February | CA $718 | | March | CA $671 | | April | CA $439 | | May | CA $497 | | June | CA $557 | | July | CA $492 | | August | CA $430 | | September | CA $499 | | October | CA $497 | | November | CA $457 | | December | CA $559 | 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 ![Fairmont Kea Lani Maui](//images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "Very nice. Pools were all well staffed and they do not let people claim loungers all day, which i really appreciate." [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Wailea? > You'll probably want to seek out the historically relevant sites while you're staying in Wailea. You can check out the beaches and coral reefs during your visit. ### How many historical hotels will I find in Wailea? > In Wailea, there are 1007 lodging options bookable on Expedia though not many historic hotels to choose from. ### What are the top historical sites and other places to visit in Wailea? > Favorite places to visit include Wailea Beach, Shops at Wailea, and Ulua Beach. A couple of additional sights to add to your agenda are Mokapu Beach and Polo Beach. ### What is a historic hotel like in Wailea? > When you book a historic hotel, you'll enjoy a vacation in a building that has a national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of historic hotels in Wailea, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel is generally the most significant aspect. For a heritage hotel, often it's the cultural value as well as how it influenced the community. ### Do historic hotels in Wailea have modern facilities? > Hotels include modern conveniences and safety features you've come to expect, but every effort is made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the normal amenities found at a contemporary hotel will also be available in a historic hotel. 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