Find Historic Hotels in Kaupakulua, HI

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Our top choices for Kaupakulua historic hotels

On the beach
Embark on a journey through Maui with Aloha Glamp

Embark on a journey through Maui with Aloha Glamp

Embark on a journey through Maui with Aloha Glamp
Haiku-Pauwela
9.6 out of 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
Sage B.
Embark on a journey through Maui with Aloha Glamp
Outdoor dining
Paia Inn - 3 Bedroom Ocean Front Beach House

Paia Inn - 3 Bedroom Ocean Front Beach House

Paia Inn - 3 Bedroom Ocean Front Beach House
Paia
10.0 out of 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
Katy F.
$2,249 nightly
The price is $2,620
Dec 16 - Dec 17
Total with taxes and fees
Paia Inn - 3 Bedroom Ocean Front Beach House
Property grounds
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 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
Wendy W.
$2,639 nightly
The price is $3,098
Jan 6 - Jan 7, 2026
Total with taxes and fees
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Beach nearby, sun loungers, beach towels
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (48)
"Good location near beach with AC in each room, many beds were good for a larger group."
Canada
Daniel C.
$450 nightly
The price is $524
Dec 12 - Dec 13
Total with taxes and fees
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
On the beach
*25% Off-Steps to Beach-AC in Every Room-Remodeled

*25% Off-Steps to Beach-AC in Every Room-Remodeled

*25% Off-Steps to Beach-AC in Every Room-Remodeled
South Kihei
10.0 out of 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
Markie Hinson H.
$553 nightly
The price is $644
Dec 12 - Dec 13
Total with taxes and fees
*25% Off-Steps to Beach-AC in Every Room-Remodeled
Outdoor pool
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 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
Mark
$351 nightly
The price is $408
Dec 16 - Dec 17
Total with taxes and fees
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
Outdoor pool, a heated pool
Remodeled ONE BEDROOM in the Maui Vista. Beach across the street!

Remodeled ONE BEDROOM in the Maui Vista. Beach across the street!

Remodeled ONE BEDROOM in the Maui Vista. Beach across the street!
South Kihei
9.6 out of 10, Exceptional, (21)
"Very close to everything, great food truck spot nearby! And beaches Just a short walk"
United States
alyssa c.
$329 nightly
The price is $383
Dec 14 - Dec 15
Total with taxes and fees
Remodeled ONE BEDROOM in the Maui Vista. Beach across the street!
Exterior
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
North Kihei
9.6 out of 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
morgan J.
$325 nightly
The price is $380
Jan 5 - Jan 6, 2026
Total with taxes and fees
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
Outdoor dining
🤙 Dec-Jan-Feb SPECIALS 🏝️ at the classic LIVE ALOHA SUITE

🤙 Dec-Jan-Feb SPECIALS 🏝️ at the classic LIVE ALOHA SUITE

🤙 Dec-Jan-Feb SPECIALS 🏝️ at the classic LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (136)
"We stayed here for 3 nights. Location was great, view was breathtaking!"
United States
Jessica v.
$583 nightly
The price is $679
Dec 19 - Dec 20
Total with taxes and fees
🤙 Dec-Jan-Feb SPECIALS 🏝️ at the classic LIVE ALOHA SUITE
Outdoor dining
200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI

200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI

200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI
Central Kihei
9.2 out of 10, Wonderful, (20)
"Nice place would stay there again. Close to beach"
United States
Colleen D.
$591 nightly
The price is $688
Dec 12 - Dec 13
Total with taxes and fees
200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI
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.
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Top Kaupakulua Hotel Reviews

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"The staff was very friendly and always ready to check your needs."
Brenda 4-night trip
Posted 23 hours ago
Maui Seaside Hotel

Frequently asked questions

What can I expect on my historical trip to Kaupakulua?
You're likely already making plans to see the historical sites during your trip to Kaupakulua. And while you are here in the area, why not also discover all of the sights in the area?
How many historically relevant hotels are located in Kaupakulua?
You'll find 78 lodging options bookable on Expedia in the larger area of Haiku, but not many designated as historic hotels.
What are the must-see historical sites and other places to visit in Kaupakulua?
Places to visit in the wider area include Maui Spa Retreat, Hoʻokipa Beach Park, and Kuau Bay Beach. You'll also find Paia Bay and Maui Garden Of Eden - Botanical Gardens & Arboretum in the area.
What is a historic hotel like in Kaupakulua?
Guests who choose historic hotels have a chance to stay in a place that's been recognized with an official historic designation. Historic hotels throughout the world have had many former lives and uses, such as castles, stately homes, palaces or even pubs, lodges, old police stations or skyscrapers. These types of hotels in Kaupakulua usually retain original characteristics like traditional architecture and period features in their communal spaces or guestrooms.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. "Historic hotel" is a term often used in the U.S., whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to put more importance on the architecture and actual building. A heritage hotel draws meaning mainly from the cultural value and how it inspired the community.
Do historic hotels in Kaupakulua have modern facilities?
Yes. Every effort is made to preserve the historic aspects and traditions, but hotel interiors are fitted with modern conveniences and safety features. Guests can expect the amenities you'd get from a hotel such as private rooms with updated bathroom facilities, WiFi, and more. In Kaupakulua, booking a historic hotel doesn't mean you're choosing a place that's uncomfortable for guests or simply rundown.

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