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Vacation 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 (S$ 645). Conversely, the most expensive month to stay in Wailea is December (S$ 2,120).

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

The cheapest day to stay in Wailea is Sunday (S$ 813). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is S$ 1,714.

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 S$ 275 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 S$ 317 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 12 May 2025
Currently, these are the lowest-priced vacation rentals in Wailea we've come across for the dates selected. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
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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
S$ 317
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,472 hotels in Wailea and price data was last updated on 12 May 2025. The average price for a hotel in Wailea is S$ 876/night.
Show all 1,472 stays
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
S$ 3,008
Avg. per night
View Deal
Mana Kai Maui
Mana Kai Maui

Mana Kai Maui

2960 S. Kihei Road, Wailea, Maui, HI, United States
1.8 km from city centre
S$ 480
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
S$ 1,444
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
S$ 598
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
S$ 997
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
S$ 1,991
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 12 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 12 May 2025.

  • How much does a holiday rental in Wailea cost?

    On average, it costs S$ 877 per night for a Wailea holiday rental, but S$ 752 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Wailea was for S$ 229 per night. If you can, try to avoid booking your rental April (as this is the most expensive month). Booking November (the cheapest month) may end up saving you money.

  • Are there any Resort holiday rentals in Wailea?

    There are 8 holiday rentals in Wailea that fall under the Resort category, the most popular is Four Seasons Resort Maui At Wailea.

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