Insights
Cheapest hotels
Where to stay

Holiday 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 May ($604). Conversely, the most expensive month to stay in Wailea is April ($3,464).

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

The cheapest day to stay in Wailea is Sunday ($845). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $2,884.

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

Save money by booking a vacation rental at least 16 days before your trip to Wailea. The lowest price found when booking 16 days ahead was $326 per night.

Find deals

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 $503 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 24 January 2026
At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Wailea. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
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
$503
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
$633
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
$873
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
Spa
$1,049
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
$1,341
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
$1,377
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,271 hotels in Wailea and price data was last updated on 24 January 2026. The average price for a hotel in Wailea is $1,540/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
$1,278
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
$3,259
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
$1,334
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
$720
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
$633
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 24 January 2026.
Scroll through the map to find holiday rentals close to the Wailea neighbourhood(s) you plan on visiting. You can find more information on a particular holiday rental within the map by clicking on its name.

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 24 January 2026.

  • How much does a holiday rental in Wailea cost?

    $1,541/night is a typical cost for a holiday rental in Wailea throughout the year. Rental prices do vary though, and you’ll find that April is the most expensive month to book, and October is the cheapest month to book. HotelsCombined users recently found Wailea holiday rentals for as low as $236/night. In general, any Wailea rental for $1,151 or less is a good deal.

  • What is the best Wailea holiday rental?

    Palms at Wailea Maui is considered the best Wailea holiday rental based on HotelsCombined user data. Palms at Wailea Maui has an average rating of 8.3/10 and 180 reviews.

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

    It’s only 22.3 km from Kahului Airport to Palms at Wailea Maui (the nearest Wailea holiday rental to the airport).

Find better results for your stay in Wailea