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Holiday hires in Wailea

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Wailea, United States
2 May — 3 May2
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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 ($921). Conversely, the most expensive month to stay in Wailea is December ($2,874).

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

The cheapest day to stay in Wailea is Sunday ($1,135). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $2,542.

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 $330 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 $385 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 25 April 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 1,476 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
$385
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,476 hotels in Wailea and price data was last updated on 25 April 2025. The average price for a hotel in Wailea is $951/night.
Show all 1,476 stays
Palms at Wailea One Bedrooms by Coldwell Banker Island Vacations
Palms at Wailea One Bedrooms by Coldwell Banker Island Vacations

Palms at Wailea One Bedrooms by Coldwell Banker Island Vacations

Wailea, Maui, HI, United States
0.8 km from city centre
Air conditioning
$780
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

Wailea, Maui, HI, United States
0.2 km from city centre
Air conditioning
$562
Avg. per night
View Deal
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
$3,560
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
$576
Avg. per night
View Deal
Wailea Elua Village - Coraltree Residence Collection
Wailea Elua Village - Coraltree Residence Collection

Wailea Elua Village - Coraltree Residence Collection

Wailea, Maui, HI, United States
0.2 km from city centre
Air conditioning
$990
Avg. per night
View Deal
Makena Surf- Coraltree Residence Collection
Makena Surf- Coraltree Residence Collection

Makena Surf- Coraltree Residence Collection

4850 Makena Alanui, Wailea, Maui, HI, United States
3.4 km from city centre
Free Wi-Fi
Parking
$1,320
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 April 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 25 April 2025.

  • How much does a holiday rental in Wailea cost?

    $952 per night is how much a holiday rental in Wailea costs, on average. $184 per night was the cheapest price recently found by our users, though anything for $790 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 December, and the cheapest time to book is March.

  • 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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