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Holiday hires 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 ($896). Conversely, the most expensive month to stay in Wailea is December ($2,851).

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

The cheapest day to stay in Wailea is Wednesday ($1,175). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $2,405.

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 $324 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 $373 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 6 June 2025
For those on a budget, these are the cheapest holiday rentals available in Wailea for the selected dates. If you have the flexibility, change the dates selected to compare prices.
Show all 1,516 holiday rentals
Maui Banyan Vacation Club
Maui Banyan Vacation Club

Maui Banyan Vacation Club

Kīhei, Maui, HI, United States
5.5 km from city centre
Air conditioning
$373
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,516 hotels in Wailea and price data was last updated on 6 June 2025. The average price for a hotel in Wailea is $1,016/night.
Show all 1,516 stays
Ho olei at Grand Wailea
Ho olei at Grand Wailea

Ho olei at Grand Wailea

146 Ho'Olei Circle, Wailea, Maui, HI, United States
0.9 km from city centre
$3,546
Avg. per night
View Deal
Mana Kai Maui
Mana Kai Maui

Mana Kai Maui

2960 S. Kihei Road, Wailea, Maui, HI, United States
1.8 km from city centre
$565
Avg. per night
View Deal
Andaz Maui at Wailea Resort - A Concept by Hyatt
Andaz Maui at Wailea Resort - A Concept by Hyatt

Andaz Maui at Wailea Resort - A Concept by Hyatt

3550 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.4 km from city centre
$1,702
Avg. per night
View Deal
Palms at Wailea Maui
Palms at Wailea Maui

Palms at Wailea Maui

3200 Wailea Alanui Dr, Wailea, Maui, HI, United States
1.0 km from city centre
Free Wi-Fi
Parking
$705
Avg. per night
View Deal
Polo Beach Club - Coraltree Residence Collection
Polo Beach Club - Coraltree Residence Collection

Polo Beach Club - Coraltree Residence Collection

34 Wailea Gateway Center Suite A102, Wailea, Maui, HI, United States
1.7 km from city centre
Free Wi-Fi
Parking
Airport shuttle
$1,176
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
Free Wi-Fi
Parking
$2,347
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 6 June 2025.
Navigate to the areas in Wailea you plan to visit to find holiday rentals that are close by. More information on a given vacation rental can be accessed by clicking the holiday rental's name within the map.

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 6 June 2025.

  • How much does a holiday rental in Wailea cost?

    $1,016 per night is how much a holiday rental in Wailea costs, on average. $294 per night was the cheapest price recently found by our users, though anything for $846 per night or less is a good deal. Keep in mind that Wailea holiday rental prices fluctuate throughout the year: the most expensive month to book is April, and the cheapest time to book is September.

  • Are there any Resort holiday rentals in Wailea?

    If you’re looking to book a Resort holiday rental in Wailea, then you have 8 to choose from. We recommend looking at Four Seasons Resort Maui At Wailea as it’s currently the most popular Resort rental among our users.

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