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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$ 821). Conversely, the most expensive month to stay in Wailea is April (C$ 1,775).

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

The cheapest day to stay in Wailea is Wednesday (C$ 844). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 2,384.

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$ 260 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$ 426 per night. There is currently one property in Wailea that can be booked for this price. Wailea Grand Champions Villas - Coraltree Residence Collection is one of the hotels that can be booked for the lowest price in Wailea. Price data was last updated on 17 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.
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
C$ 426
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
C$ 1,079
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,524 hotels in Wailea and price data was last updated on 17 September 2025. The average price for a hotel in Wailea is C$ 847/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
C$ 2,617
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$ 1,001
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
C$ 1,079
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 17 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 17 September 2025.

  • How much does a vacation rental in Wailea cost?

    Wailea vacation rentals are C$ 847/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 November is often the cheapest month to book. Recently, our users found rentals for C$ 113/night - which is currently the cheapest price. Keep in mind that anything C$ 687/night or less is still considered a good deal.

  • What’s the closest vacation rental to Kahului Airport?

    It’s only 23.2 km from Kahului Airport to Wailea Grand Champions Villas - Coraltree Residence Collection (the nearest Wailea vacation rental to the airport).

  • 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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