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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 May ($761). Conversely, the most expensive month to stay in Wailea is April ($1,580).

What is the cheapest day to stay in a vacation rental in Wailea?

The cheapest day to stay in Wailea is Saturday ($703). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,986.

How far ahead should you book a vacation rental in Wailea?

Save money by booking a vacation rental at least 2 days before your trip to Wailea. The lowest price found when booking 2 days ahead was $329 per night.
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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 $779 per night. There is currently one property in Wailea that can be booked for this price. Wailea Grand Champions Villas - Coraltree Residence Collection is one of the hotels that can be booked for the lowest price in Wailea. Price data was last updated on 25 October 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.
Wailea Grand Champions Villas - Coraltree Residence Collection
Wailea Grand Champions Villas - Coraltree Residence Collection

Wailea Grand Champions Villas - Coraltree Residence Collection

155 Wailea Ike Place, Wailea, Maui, HI, United States
0.2 km from city centre
Free Wi-Fi
$779
Avg. per night
View Deal
Elua Village
Elua Village

Elua Village

Wailea, Maui, HI, United States
0.2 km from city centre
Air conditioning
Airport shuttle
$1,489
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,262 hotels in Wailea and price data was last updated on 25 October 2025. The average price for a hotel in Wailea is $1,024/night.
Palms At Wailea Maui
Palms At Wailea Maui

Palms At Wailea Maui

3200 Wailea Alanui Dr, Wailea, Maui, HI, United States
0.9 km from city centre
Free Wi-Fi
Parking
Spa
$492
Avg. per night
View Deal
Residence Inn by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

75 Wailea Ike, Wailea, Maui, HI, United States
0.3 km from city centre
Free Wi-Fi
$621
Avg. per night
View Deal
Wailea Grand Champions Villas - Coraltree Residence Collection
Wailea Grand Champions Villas - Coraltree Residence Collection

Wailea Grand Champions Villas - Coraltree Residence Collection

155 Wailea Ike Place, Wailea, Maui, HI, United States
0.2 km from city centre
Free Wi-Fi
$779
Avg. per night
View Deal
Wailea Beach Villas
Wailea Beach Villas

Wailea Beach Villas

3800 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.6 km from city centre
Airport shuttle
$1,689
Avg. per night
View Deal

Where to stay in Wailea

Explore different neighbourhoods and areas within Wailea to find the perfect location for your stay. Map data was last updated on 25 October 2025.
Scroll through the map to find holiday rentals close to the Wailea neighbourhood(s) you plan on visiting. You can find more information on a particular holiday rental within the map by clicking on its name.

Facts about staying in Wailea

Find useful tips and insights about staying in Wailea to help you make the most of your experience. FAQs were last updated on 25 October 2025.

  • How much does a holiday rental in Wailea cost?

    $1,025/night is a typical cost for a holiday rental in Wailea throughout the year. Rental prices do vary though, and you’ll find that April is the most expensive month to book, and October is the cheapest month to book. HotelsCombined users recently found Wailea holiday rentals for as low as $243/night. In general, any Wailea rental for $797 or less is a good deal.

  • Are there any Resort holiday rentals in Wailea?

    At the moment, there are 8 properties listed as a Resort holiday rental in Wailea. A popular Resort in Wailea amongst our users is Grand Wailea, A Waldorf Astoria Resort.

Find better results for your stay in Wailea

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