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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$ 586). Conversely, the most expensive month to stay in Wailea is November (S$ 1,673).

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

The cheapest day to stay in Wailea is Tuesday (S$ 596). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is S$ 1,758.

How far ahead should you book a vacation rental in Wailea?

Save money by booking a vacation rental at least 4 days before your trip to Wailea. The lowest price found when booking 4 days ahead was S$ 239 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$ 435 per night. There is currently one property in Wailea that can be booked for this price. Palms at Wailea Maui is one of the hotels that can be booked for the lowest price in Wailea. Price data was last updated on 13 March 2026
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.
Palms at Wailea Maui
Palms at Wailea Maui

Palms at Wailea Maui

Wailea, Maui, HI, United States
0.9 km from city centre
Air conditioning
S$ 435
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

155 Wailea Ike Place, Wailea, Maui, HI, United States
0.2 km from city centre
Free Wi-Fi
S$ 454
Avg. per night
View Deal
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$ 489
Avg. per night
View Deal
Wailea Elua Village
Wailea Elua Village

Wailea Elua Village

Wailea, Maui, HI, United States
0.3 km from city centre
Air conditioning
Airport shuttle
Spa
S$ 753
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
S$ 889
Avg. per night
View Deal
Makena Surf - Coraltree Residence Collection
Makena Surf - Coraltree Residence Collection

Makena Surf - Coraltree Residence Collection

Wailea, Maui, HI, United States
3.4 km from city centre
Air conditioning
S$ 891
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,268 hotels in Wailea and price data was last updated on 13 March 2026. The average price for a hotel in Wailea is S$ 910/night.
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
S$ 966
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
S$ 2,386
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
S$ 1,176
Avg. per night
View Deal
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$ 489
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
S$ 611
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 13 March 2026.
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 13 March 2026.

  • How much does a holiday rental in Wailea cost?

    On average, it costs S$ 911 per night for a Wailea holiday rental, but S$ 631 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$ 179 per night. If you can, try to avoid booking your rental November (as this is the most expensive month). Booking October (the cheapest month) may end up saving you money.

  • What is the best Wailea holiday rental?

    While there may be other great holiday rentals in Wailea to choose from, Palms at Wailea Maui is currently considered the best, based on 180 HotelsCombined reviews and an average rating of 7.9/10.

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

    If you’re looking to stay close to Kahului Airport for your trip to Wailea, then consider booking a Palms at Wailea Maui holiday rental. This holiday apartment is just 22.3 km away from the Wailea airport.

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