Wailea 5-star Hotels
Compare rates for 5-star hotels in Wailea, HI from hundreds of popular travel sites on HotelsCombined.
Wailea, United States
2 May — 3 May2
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Travel insights for hotels in Wailea
Use these up-to-date, data-driven insights about booking a hotel in Wailea including ideal times to book, pricing trends, and more.
What is the cheapest month to book a hotel in Wailea?
The cheapest month to book a hotel in Wailea is October (C$ 1,240). Conversely, the most expensive month to stay in Wailea is December (C$ 2,154).
What is the cheapest day to stay in a hotel in Wailea?
The cheapest day to stay in Wailea is Saturday (C$ 1,404). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 2,649.
Cheapest 5-star hotels in Wailea
Discover affordable 5-star hotels in Wailea that provide a quality experience without breaking the bank. 5-star hotels in Wailea can be found for as low as C$ 1,189 per night. Price data was last updated on 25 April 2025
These are the lowest-priced 5-star hotels our users have recently found in Wailea. Prices may vary based on dates selected and hotel location.
Show all 3 5-star hotels
4100 Wailea Alanui Drive, Wailea, Maui, HI, United States
1.6 km from city centre
C$ 1,189
Avg. per night
C$ 1,191
Avg. per night
3850 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.7 km from city centre
C$ 1,240
Avg. per night
Other star-rated hotels in Wailea
Hotels that are booked the most in each class receive the “Most popular” badge. Hotels with the “Best value” have the most attractive prices based on their popularity. Price data was last updated on 25 April 2025.
Not set on a 5-star hotel? We’ve got plenty of other options for you to choose from. These are the most popular and best value properties in Wailea based on hotel class.
4 stars
3550 Wailea Alanui Drive, Wailea, Maui, HI, United States
C$ 1,456
146 Ho'Olei Circle, Wailea, Maui, HI, United States
C$ 3,151
3800 Wailea Alanui Drive, Wailea, Maui, HI, United States
C$ 2,114
3700 Wailea Alanui Drive, Wailea, Maui, HI, United States
C$ 1,117
3 stars
75 Wailea Ike, Wailea, Maui, HI, United States
C$ 681
3200 Wailea Alanui Dr, Wailea, Maui, HI, United States
C$ 596
Other accommodations in Wailea
Find deals on places to stay in Wailea that are not hotels. These are just a few of the most popular hostels and vacation rentals in the area. Pricing information was last updated on 25 April 2025.
Looking for something less traditional for your stay? Find the perfect hostel or vacation rental for your trip in Wailea.
Show all 1,476 stays
3850 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.7 km from city centre
C$ 1,240
Avg. per night
4100 Wailea Alanui Drive, Wailea, Maui, HI, United States
1.6 km from city centre
C$ 1,189
Avg. per night
C$ 1,191
Avg. per night