Holiday rentals in Wailea
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Travel insights for holiday rentals in Wailea
Use these up-to-date, data-driven insights about booking a holiday rental in Wailea including ideal times to book, pricing trends, and more.
What is the cheapest month to book a vacation rental in Wailea?
The cheapest month to book a vacation rental in Wailea is October ($1,095). Conversely, the most expensive month to stay in Wailea is December ($3,600).
What is the cheapest day to stay in a vacation rental in Wailea?
The cheapest day to stay in Wailea is Sunday ($1,380). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $2,912.
How far ahead should you book a vacation rental in Wailea?
Save money by booking a vacation rental at least 9 days before your trip to Wailea. The lowest price found when booking 9 days ahead was $358 per night.
Cheapest holiday rentals in Wailea, Hawaii
Discover affordable stays in Wailea that provide a quality experience without breaking the bank. Hotels in Wailea can be found for as low as $413 per night. There is currently one property in Wailea that can be booked for this price. Maui Banyan Vacation Club is one of the hotels that can be booked for the lowest price in Wailea. Price data was last updated on 12 May 2025
At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Wailea. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Show all 1,472 holiday rentals
$413
Avg. per night
Other accommodations in Wailea
Find the perfect holiday rental for your stay in Wailea. There are 1,472 hotels in Wailea and price data was last updated on 12 May 2025. The average price for a hotel in Wailea is $1,142/night.
Show all 1,472 stays
3200 Wailea Alanui Dr, Wailea, Maui, HI, United States
1.0 km from city centre
Free Wi-Fi
Parking
$780
Avg. per night
34 Wailea Gateway Center Suite A102, Wailea, Maui, HI, United States
1.7 km from city centre
Free Wi-Fi
Parking
Airport shuttle
$1,300
Avg. per night
3800 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.6 km from city centre
Free Wi-Fi
Parking
$2,595
Avg. per night
$1,459
Avg. per night
75 Wailea Ike, Wailea, Maui, HI, United States
0.3 km from city centre
Free Wi-Fi
$834
Avg. per night