Title: Book the Best HISTORIC Hotels in Kaupakulua in 2026 | Expedia.ca [Hotels in Kaupakulua](https://expedia.ca/Kaupakulua-Hotels.d11836.Travel-Guide-Hotels)[Vacation Rentals in Kaupakulua](https://expedia.ca/Kaupakulua-Vacation-Rentals.d11836.Travel-Guide-VacationRentals)[Kaupakulua Car Rentals](https://expedia.ca/Car-Rentals-In-Kaupakulua.d11836.Car-Rental-Guide)[Kaupakulua Vacation Packages](https://expedia.ca/Kaupakulua.d11836.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/historic.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Kaupakulua, HI from CA $527 - ![](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 Kaupakulua Historic Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=11836&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=11836&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=11836&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=11836&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Kaupakulua historic hotels ![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) ![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 [](https://www.expedia.ca/Haiku-Hotels-Embark-On-A-Journey-Through-Maui-With-Aloha-Glamp.h27441539.Hotel-Information) Haiku-Pauwela 9.6/10 Exceptional (38) "We booked this Jeep for our honeymoon stay on Maui. It was a wonderful drive, handled every road we were on beautiful, and provided a great place to sleep. Sebastian had all the necessities packed and it made for an easy trip. Couldn’t be happier. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sage B. [](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) ![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) ![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) ### Paia Inn - 3 Bedroom Ocean Front Beach House [](https://www.expedia.ca/Paia-Hotels-Paia-Inn-3-Bedroom-Ocean-Front-Beach-House.h64399140.Hotel-Information) 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 $2,754 CA $3,577 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Paia-Hotels-Paia-Inn-3-Bedroom-Ocean-Front-Beach-House.h64399140.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) ![Interior](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/3fdca3f0.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) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29880000/29873100/29873066/972eccb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.Hotel-Information) Makawao 10/10 Exceptional (71) "What a special property. The location is perfect. We rented it for a work training and it was excellent since everyone has their own room/bathroom but we were able to meet in the large living room for evening presentations/discussions. The host was responsive with questions. It was very clean and check-in was easy. I hope to return again for both this meeting and with family for vacation. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy W. CA $2,197 CA $4,268 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Makawao-Hotels-Historic-Upcountry-Maui-Property-With-Pool.h29873066.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) ![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) ### Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental [](https://www.expedia.ca/Kihei-Hotels-Pacific-Shores-2bd-2bth-Kihei-MAUI-Condo-Kamaole-Beach-HAWAII-Vacation-Rental.h18993493.Hotel-Information) South Kihei 9.6/10 Exceptional (48) "Good location near beach with AC in each room, many beds were good for a larger group." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Daniel C. CA $274 CA $722 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Kihei-Hotels-Pacific-Shores-2bd-2bth-Kihei-MAUI-Condo-Kamaole-Beach-HAWAII-Vacation-Rental.h18993493.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) ![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) ![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) ### \*25% Off-Steps to Beach-AC in Every Room-Remodeled [](https://www.expedia.ca/Kihei-Hotels-25-Off-Steps-To-Beach-AC-In-Every-Room-Remodeled.h71390255.Hotel-Information) 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 $249 CA $867 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Kihei-Hotels-25-Off-Steps-To-Beach-AC-In-Every-Room-Remodeled.h71390255.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/19000000/18980000/18978200/18978176/79fb7e95.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) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18978200/18978176/265e1013.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! [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18978176.Hotel-Information) North Kihei 9.8/10 Exceptional (297) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $154 CA $562 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18978176.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33940000/33932200/33932189/dd40bf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33940000/33932200/33932189/907ecfe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932200/33932189/536c7ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33932200/33932189/649c1f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Remodeled ONE BEDROOM in the Maui Vista. Beach across the street! [](https://www.expedia.ca/Kihei-Hotels-Remodeled-ONE-BEDROOM-In-The-Maui-Vista-Beach-Across-The-Street.h33932189.Hotel-Information) South Kihei 9.6/10 Exceptional (21) "Very close to everything, great food truck spot nearby! And beaches Just a short walk" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) alyssa c. CA $217 CA $527 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Kihei-Hotels-Remodeled-ONE-BEDROOM-In-The-Maui-Vista-Beach-Across-The-Street.h33932189.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) ![Smart TV, DVD player, books, streaming services](https://images.trvl-media.com/lodging/19000000/19000000/18991900/18991875/c51e7b8b.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) ### AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles! [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18991875.Hotel-Information) North Kihei 9.6/10 Exceptional (287) "Had a great experience here it was close to everything in town and near alot of cool beaches! Would definitely return" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) morgan J. CA $150 CA $557 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Kihei-Hotels-Reviews-Say-Clean.h18991875.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) ![Exterior](https://images.trvl-media.com/lodging/33000000/33000000/32999500/32999423/f1e45bda.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) ![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) ### 🤙 Dec-Jan-Feb SPECIALS 🏝️ at the classic LIVE ALOHA SUITE [](https://www.expedia.ca/Kihei-Hotels-Welcome-Back-To-The-Clean-Live-Aloha-Suite.h32999423.Hotel-Information) North Kihei 10/10 Exceptional (136) "We stayed here for 3 nights. Location was great, view was breathtaking!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica v. CA $371 CA $935 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Kihei-Hotels-Welcome-Back-To-The-Clean-Live-Aloha-Suite.h32999423.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) ![Interior](https://images.trvl-media.com/lodging/42000000/41540000/41534600/41534563/0f082a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI [](https://www.expedia.ca/Kihei-Hotels-200ft-From-The-Beach-Restaurants-King-Twin-Beds-Pool-WIFI.h41534563.Hotel-Information) 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 $293 CA $955 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Kihei-Hotels-200ft-From-The-Beach-Restaurants-King-Twin-Beds-Pool-WIFI.h41534563.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=2025-12-26&endDate=2025-12-27®ionId=11836&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Kaupakulua Hotel Reviews ![Maui Seaside Hotel](https://images.trvl-media.com/lodging/1000000/20000/19700/19630/b53bdaab_y.jpg) ### Maui Seaside Hotel 10/10 Excellent "The staff was very friendly and always ready to check your needs." [](https://expedia.ca/Kahului-Hotels-Maui-Seaside-Hotel.h19630.Hotel-Information) ![Maui Beach Hotel](https://images.trvl-media.com/lodging/1000000/20000/18600/18554/d9caacb9_y.jpg) ### Maui Beach Hotel 10/10 Excellent "Tiana was great. Very friendly and very helpful." [](https://expedia.ca/Kahului-Hotels-Maui-Beach-Hotel.h18554.Hotel-Information) ![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "very nicely rennovated hotel and rooms very convenient shuttle service very good food the staff was sometimes variable in quality and experience the concierge service can be improved - lacking concrete tips and details related to trip to hana, no supporting documentation, poor leasing staff " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ## Frequently asked questions ### What can I expect on my historical trip to Kaupakulua? ### How many historically relevant hotels are located in Kaupakulua? ### What are the must-see historical sites and other places to visit in Kaupakulua? ### What is a historic hotel like in Kaupakulua? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Kaupakulua have modern facilities? ## Explore a world of travel with Expedia - 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