Find Historic Hotels in Wailea, HI

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Wailea Historic Hotels

Tonight
Dec 7 - Dec 8
Tomorrow
Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top Wailea Historic Hotels

Beach nearby
130K Hawaiian Reno on Wailea Blue Golf *Ocean View

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

Wailea
10.0 out of 10, Exceptional, (34)
"We loved our stay at this condo in Wailea!! The golf course and property were meticulously maintained and it was such a peaceful location. We wish we could’ve stayed longer and would definitely stay here again!"
United States
Angie G.
$509 nightly
The price is $590
Dec 13 - Dec 14
Total with taxes and fees
130K Hawaiian Reno on Wailea Blue Golf *Ocean View
Outdoor pool
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

Wailea
10.0 out of 10, Exceptional, (58)
"Great place and attentive owners"
United States
Darren P.
$840 nightly
The price is $977
Dec 15 - Dec 16
Total with taxes and fees
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
A heated pool
Vacation in Paradise at our charming condo by the best of everything Maui offers

Vacation in Paradise at our charming condo by the best of everything Maui offers

Wailea
9.8 out of 10, Exceptional, (102)
"Very nice location with nice view off lanai. Ocean access from complex."
United States
Lisa L.
$762 nightly
The price is $962
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vacation in Paradise at our charming condo by the best of everything Maui offers
Sun loungers, beach towels
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views

Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views

Wailea
9.8 out of 10, Exceptional, (60)
"Best view from the wrap-around porch on the second floor of any of the condos we’ve stayed at on the Grand Champions property. Check-in was clear, kitchen was well appointed and the WiFi more than sufficient for all of us. "
United States
Rose N.
$819 nightly
The price is $952
Dec 13 - Dec 14
Total with taxes and fees
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views
Beach nearby
100KContemporaryHawaiian Reno in Wailea-Beach/Golf

100KContemporaryHawaiian Reno in Wailea-Beach/Golf

Wailea
10.0 out of 10, Exceptional, (38)
"Great location and every detail was perfect."
Canada
Krista W.
$685 nightly
The price is $793
Dec 26 - Dec 27
Total with taxes and fees
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
On the beach
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.
$233 nightly
The price is $272
Dec 9 - Dec 10
Total with taxes and fees
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
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.
$1,690 nightly
The price is $1,968
Dec 10 - Dec 11
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

Makawao
10.0 out of 10, Exceptional, (71)
"This property was indescribable! Our stay was amazing and the host was so very accommodating! Check-in was a breeze and every room was meticulously cleaned, arranged, and ready for our group. "
United States
James B.
$2,384 nightly
The price is $2,791
Dec 11 - Dec 12
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

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.
$456 nightly
The price is $530
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

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.
$578 nightly
The price is $672
Dec 12 - Dec 13
Total with taxes and fees
*25% Off-Steps to Beach-AC in Every Room-Remodeled
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

Price trends for hotels in Wailea

Less expensive
More expensive
This month
Next month
October
February
$543
$589
Month
Price
January
$589
February
$620
March
$595
April
$506
May
$473
June
$487
July
$486
August
$447
September
$450
October
$446
November
$480
December
$543
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

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 "
Christophe 7-night trip
Posted 8 days ago
Fairmont Kea Lani Maui

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 1200 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. When you choose a historic hotel in Wailea, don't worry that you'll find a place that's uncomfortable or rundown.

Explore a world of travel with Expedia