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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 October ($1,220). Conversely, the most expensive month to stay in Wailea is April ($2,672).

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

The cheapest day to stay in Wailea is Saturday ($1,034). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $3,287.

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 $319 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 $341 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 9 September 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.
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
$341
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,526 hotels in Wailea and price data was last updated on 9 September 2025. The average price for a hotel in Wailea is $1,081/night.
Grand Wailea, A Waldorf Astoria Resort
Grand Wailea, A Waldorf Astoria Resort

Grand Wailea, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.7 km from city centre
$1,019
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
$3,210
Avg. per night
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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
$1,155
Avg. per night
View Deal
Hotel Wailea
Hotel Wailea

Hotel Wailea

555 Kaukahi Street, Wailea, Maui, HI, United States
1.6 km from city centre
Free Wi-Fi
$1,308
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 9 September 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 9 September 2025.

  • How much does a holiday rental in Wailea cost?

    $1,081/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 August is the cheapest month to book. HotelsCombined users recently found Wailea holiday rentals for as low as $301/night. In general, any Wailea rental for $881 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

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 hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly. Discover hotel discounts now and make your hotel reservation today.