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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 ($770). Conversely, the most expensive month to stay in Wailea is June ($2,665).

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

The cheapest day to stay in Wailea is Saturday ($939). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $2,275.

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

Save money by booking a vacation rental at least 10 days before your trip to Wailea. The lowest price found when booking 10 days ahead was $331 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 $296 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 July 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.
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
$296
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,527 hotels in Wailea and price data was last updated on 25 July 2025. The average price for a hotel in Wailea is $1,032/night.
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
$3,282
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
$1,243
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
$506
Avg. per night
View Deal
Wailea Sunset Condo - Ekolu #607
Wailea Sunset Condo - Ekolu #607

Wailea Sunset Condo - Ekolu #607

Wailea, Maui, HI, United States
0.7 km from city centre
$540
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
$984
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 July 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 July 2025.

  • How much does a holiday rental in Wailea cost?

    $1,033 per night is how much a holiday rental in Wailea costs, on average. $311 per night was the cheapest price recently found by our users, though anything for $821 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 June, and the cheapest time to book is June.

  • 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.

Find better results for your stay in Wailea

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $151. Discover hotel discounts now and make your hotel reservation today.