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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 May (S$ 568). Conversely, the most expensive month to stay in Wailea is April (S$ 1,179).

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

The cheapest day to stay in Wailea is Saturday (S$ 524). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is S$ 1,482.

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 S$ 245 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$ 581 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 26 October 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.
Wailea Grand Champions Villas - Coraltree Residence Collection
Wailea Grand Champions Villas - Coraltree Residence Collection

Wailea Grand Champions Villas - Coraltree Residence Collection

155 Wailea Ike Place, Wailea, Maui, HI, United States
0.2 km from city centre
Free Wi-Fi
S$ 581
Avg. per night
View Deal
Elua Village
Elua Village

Elua Village

Wailea, Maui, HI, United States
0.2 km from city centre
Air conditioning
Airport shuttle
S$ 1,111
Avg. per night
View Deal
Polo Beach Club - Coraltree Residence Collection
Polo Beach Club - Coraltree Residence Collection

Polo Beach Club - Coraltree Residence Collection

Wailea, Maui, HI, United States
1.7 km from city centre
Air conditioning
Airport shuttle
S$ 1,299
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,262 hotels in Wailea and price data was last updated on 26 October 2025. The average price for a hotel in Wailea is S$ 764/night.
Wailea Sunset Condo - Ekolu #607
Wailea Sunset Condo - Ekolu #607

Wailea Sunset Condo - Ekolu #607

Wailea, Maui, HI, United States
0.7 km from city centre
Air conditioning
S$ 550
Avg. per night
View Deal
Polo Beach Club - Coraltree Residence Collection
Polo Beach Club - Coraltree Residence Collection

Polo Beach Club - Coraltree Residence Collection

Wailea, Maui, HI, United States
1.7 km from city centre
Air conditioning
Airport shuttle
S$ 1,299
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
0.9 km from city centre
Free Wi-Fi
Parking
Spa
S$ 371
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 26 October 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 26 October 2025.

  • How much does a holiday rental in Wailea cost?

    On average, it costs S$ 765 per night for a Wailea holiday rental, but S$ 595 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$ 181 per night. If you can, try to avoid booking your rental April (as this is the most expensive month). Booking October (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 Grand Wailea, A Waldorf Astoria Resort.

Find better results for your stay in Wailea

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