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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 November (S$ 547). Conversely, the most expensive month to stay in Wailea is April (S$ 1,541).

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

The cheapest day to stay in Wailea is Wednesday (S$ 666). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is S$ 1,895.

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$ 242 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$ 258 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 15 September 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.
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$ 258
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,525 hotels in Wailea and price data was last updated on 15 September 2025. The average price for a hotel in Wailea is S$ 771/night.
Hotel Wailea
Hotel Wailea

Hotel Wailea

555 Kaukahi Street, Wailea, Maui, HI, United States
1.6 km from city centre
Free Wi-Fi
S$ 1,023
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$ 616
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$ 315
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$ 1,179
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$ 1,425
Avg. per night
View Deal
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$ 769
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$ 2,430
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$ 958
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 15 September 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 15 September 2025.

  • How much does a holiday rental in Wailea cost?

    On average, it costs S$ 771 per night for a Wailea holiday rental, but S$ 627 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$ 105 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 Grand Wailea, A Waldorf Astoria Resort.

Find better results for your stay in Wailea

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