Insights
Where to stay

Vacation rentals in Wailea

Search and compare Wailea, HI holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

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$ 622). Conversely, the most expensive month to stay in Wailea is December (S$ 1,947).

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

The cheapest day to stay in Wailea is Saturday (S$ 878). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 1,670.

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$ 270 per night.
Find deals

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,498 hotels in Wailea and price data was last updated on 15 June 2025. The average price for a hotel in Wailea is S$ 924/night.
Show all 1,498 stays
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$ 588
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$ 979
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$ 1,956
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
S$ 419
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 June 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 June 2025.

  • How much does a holiday rental in Wailea cost?

    On average, it costs S$ 925 per night for a Wailea holiday rental, but S$ 717 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$ 220 per night. If you can, try to avoid booking your rental June (as this is the most expensive month). Booking June (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.

Find better results for your stay in Wailea