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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$ 719). Conversely, the most expensive month to stay in Wailea is December (C$ 2,296).

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

The cheapest day to stay in Wailea is Sunday (C$ 1,016). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 1,903.

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 C$ 290 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$ 335 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 28 May 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.
Show all 1,477 vacation 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
C$ 335
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,477 hotels in Wailea and price data was last updated on 28 May 2025. The average price for a hotel in Wailea is C$ 901/night.
Show all 1,477 stays
Hotel Wailea
Hotel Wailea

Hotel Wailea

555 Kaukahi Street, Wailea, Maui, HI, United States
1.6 km from city centre
Free Wi-Fi
C$ 1,182
Avg. per night
View Deal
Residence Inn by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

75 Wailea Ike, Wailea, Maui, HI, United States
0.3 km from city centre
Free Wi-Fi
C$ 676
Avg. per night
View Deal
Palms at Wailea Maui
Palms at Wailea Maui

Palms at Wailea Maui

3200 Wailea Alanui Dr, Wailea, Maui, HI, United States
1.0 km from city centre
Free Wi-Fi
Parking
C$ 632
Avg. per night
View Deal
Polo Beach Club - Coraltree Residence Collection
Polo Beach Club - Coraltree Residence Collection

Polo Beach Club - Coraltree Residence Collection

34 Wailea Gateway Center Suite A102, Wailea, Maui, HI, United States
1.7 km from city centre
Free Wi-Fi
Parking
Airport shuttle
C$ 1,053
Avg. per night
View Deal
Wailea Beach Villas
Wailea Beach Villas

Wailea Beach Villas

3800 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.6 km from city centre
Free Wi-Fi
Parking
C$ 2,103
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 28 May 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 28 May 2025.

  • How much does a vacation rental in Wailea cost?

    Wailea vacation rentals are C$ 901/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 June is often the cheapest month to book. Recently, our users found rentals for C$ 169/night - which is currently the cheapest price. Keep in mind that anything C$ 771/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, Four Seasons Resort Maui At Wailea is currently the most popular Resort rental in the city.

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