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Vacation rentals in Wailea

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Travel insights for vacation rentals in Wailea

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 818). Conversely, the most expensive month to stay in Wailea is April (C$ 1,791).

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

The cheapest day to stay in Wailea is Saturday (C$ 693). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 2,203.

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 C$ 261 per night.
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Cheapest vacation 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 C$ 338 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 5 September 2025
Out of the vacation rentals in Wailea we've come across, these properties are priced the lowest. 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
C$ 338
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,527 hotels in Wailea and price data was last updated on 5 September 2025. The average price for a hotel in Wailea is C$ 885/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
C$ 1,138
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
C$ 3,381
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
C$ 1,158
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 5 September 2025.
Scroll through the map to find vacation rentals close to the Wailea neighborhood(s) you plan on visiting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 5 September 2025.

  • How much does a vacation rental in Wailea cost?

    Wailea vacation rentals are C$ 885/night on average. However, you may find that prices fluctuate depending on the time of year. For example, April is the most expensive month to book a vacation rental in Wailea, and August is often the cheapest month to book. Recently, our users found rentals for C$ 246/night - which is currently the cheapest price. Keep in mind that anything C$ 721/night or less is still considered a good deal.

  • Are there any Resort vacation rentals in Wailea?

    Yes, there are 8 Resort vacation rentals in Wailea. According to our data, Grand Wailea, A Waldorf Astoria Resort is currently the most popular Resort rental in the city.

Find better results for your stay in Wailea

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