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Vacation rentals in Wailea

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Wailea, United States
29 Apr — 30 Apr2
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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$ 716). Conversely, the most expensive month to stay in Wailea is December (C$ 2,236).

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

The cheapest day to stay in Wailea is Sunday (C$ 883). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 1,978.

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$ 291 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$ 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 22 April 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 1,476 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$ 341
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,476 hotels in Wailea and price data was last updated on 22 April 2025. The average price for a hotel in Wailea is C$ 839/night.
Show all 1,476 stays
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$ 1,223
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$ 3,130
Avg. per night
View Deal
Palms at Wailea One Bedrooms by Coldwell Banker Island Vacations
Palms at Wailea One Bedrooms by Coldwell Banker Island Vacations

Palms at Wailea One Bedrooms by Coldwell Banker Island Vacations

Wailea, Maui, HI, United States
0.8 km from city centre
Air Conditioning
C$ 688
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
C$ 515
Avg. per night
View Deal
Makena Surf- Coraltree Residence Collection
Makena Surf- Coraltree Residence Collection

Makena Surf- Coraltree Residence Collection

4850 Makena Alanui, Wailea, Maui, HI, United States
3.4 km from city centre
Free Wi-Fi
Parking
C$ 1,164
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$ 577
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$ 2,106
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 22 April 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 22 April 2025.

  • How much does a vacation rental in Wailea cost?

    Wailea vacation rentals are C$ 840/night on average. However, you may find that prices fluctuate depending on the time of year. For example, December is the most expensive month to book a vacation rental in Wailea, and March is often the cheapest month to book. Recently, our users found rentals for C$ 163/night - which is currently the cheapest price. Keep in mind that anything C$ 696/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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