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 $407 - ![](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 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7739&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wailea Historic Hotels ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57590000/57584900/57584863/209de1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57590000/57584900/57584863/628aceb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/58000000/57590000/57584900/57584863/5f393287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/58000000/57590000/57584900/57584863/4bfd25da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 100KContemporaryHawaiian Reno in Wailea-Beach/Golf Wailea 10/10 Exceptional (38) "Great location and every detail was perfect." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Krista W. CA $368 CA $844 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Kihei-Hotels-100KContemporaryHawaiian-Reno-In-Wailea-BeachGolf.h57584863.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/32000000/31950000/31949200/31949120/9db2dd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31950000/31949200/31949120/c718919f.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) ![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) ### 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all! Wailea 10/10 Exceptional (57) "Great accommodation and perfect location on Maui." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary S. CA $566 CA $1,404 total includes taxes & fees Nov 21 - Nov 22 [](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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34120000/34112200/34112190/9b4a350b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34120000/34112200/34112190/a129221c.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) ### Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views Wailea 9.8/10 Exceptional (59) "Amazing views, amenities and location. Can’t wait to visit again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan S. CA $535 CA $1,299 total includes taxes & fees Nov 1 - Nov 2 [](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) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/9285d001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27441600/27441539/2db77916.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) ### Embark on a journey through Maui with Aloha Glamp Haiku-Pauwela 9.6/10 Exceptional (38) "Everything we needed for our short stay on Maui. The jeep was clean and efficient, the tent was comfortable and easy to use. Will definitely rent again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desirae B. CA $166 CA $407 total includes taxes & fees Dec 1 - Dec 2 [](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/65000000/64400000/64399200/64399140/95e8c60c.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... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katy F. CA $1,817 CA $2,384 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Paia-Hotels-Paia-Inn-3-Bedroom-Ocean-Front-Beach-House.h64399140.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/97b49aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/1ac53446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/3b819fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, stereo](https://images.trvl-media.com/lodging/19000000/18980000/18973900/18973882/4ace5080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In Paia 10/10 Exceptional (176) "Was pleasant and quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donovan W. CA $418 CA $1,197 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Paia-Hotels-Charming-Ocean-View-Home-With-Central-AC-Walk-To-Downtown-Paia-And-Beaches.h18973882.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) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/19000000/19000000/18993500/18993493/ac4a560a.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) "Our family of 6 enjoyed our stay at this condo. Short walk to the beach where we snorkeled and boogie boarded. We also saw whales jumping right at sunset which was one of the most amazing things I have seen in my life. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike h. CA $278 CA $737 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) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/c4332c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/93574a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 Makawao 10/10 Exceptional (70) "There is absolutely nothing we could think of that was missing from our week at Banyon Tree! The property is beautiful, lovingly maintained, and made this our best trip to Hawaii ever!! Actually, our best-ever family vacation! Plenty of room for swimming, playing Capture the Flag, enjoying family dinners, playing card and table games, and just hanging out. We enjoyed seeing the turtles at Ho’okepa Beach, playing in the river at Íao State Park, and shopping local markets. Comfortable island... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheridan B. CA $2,230 CA $4,440 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.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/42000000/41540000/41534600/41534563/66397b46.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) ![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) ### 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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen D. CA $195 CA $855 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Kihei-Hotels-200ft-From-The-Beach-Restaurants-King-Twin-Beds-Pool-WIFI.h41534563.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) ![Smart TV, books](https://images.trvl-media.com/lodging/72000000/71400000/71390300/71390255/b524e992.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) ![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) ### \*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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Markie Hinson H. CA $247 CA $884 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Kihei-Hotels-25-Off-Steps-To-Beach-AC-In-Every-Room-Remodeled.h71390255.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=2025-11-14&endDate=2025-11-15®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 | | --- | --- | --- | | April | August | CA $500 | | Month | Price | | --- | --- | | January | CA $593 | | February | CA $542 | | March | CA $595 | | April | CA $424 | | May | CA $549 | | June | CA $735 | | July | CA $578 | | August | CA $937 | | September | CA $547 | | October | CA $934 | | November | CA $500 | | December | CA $521 | 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 "Amazing. Our favourite hot on the planet! " [](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 1179 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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