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Holiday rentals in Wailea

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Travel insights for holiday rentals in Wailea

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Wailea.

What is the cheapest month to book a vacation rental in Wailea?

The cheapest month to book a vacation rental in Wailea is March ($792). Conversely, the most expensive month to stay in Wailea is November ($2,236).

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

The cheapest day to stay in Wailea is Tuesday ($826). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $2,282.

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 $317 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 $552 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 17 April 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.
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
$552
Avg. per night
View Deal
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
$587
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
$1,000
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
$1,288
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
3.3 km from city centre
Air conditioning
$1,324
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,277 hotels in Wailea and price data was last updated on 17 April 2026. The average price for a hotel in Wailea is $1,240/night.
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
$3,245
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
$1,519
Avg. per night
View Deal
Fairmont Kea Lani, Maui
Fairmont Kea Lani, Maui

Fairmont Kea Lani, Maui

4100 Wailea Alanui Drive, Wailea, Maui, HI, United States
1.6 km from city centre
$1,340
Avg. per night
View Deal
Hotel Wailea
Hotel Wailea

Hotel Wailea

555 Kaukahi Street, Wailea, Maui, HI, United States
1.6 km from city centre
Free Wi-Fi
$1,245
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
$797
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 17 April 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 17 April 2026.

  • How much does a holiday rental in Wailea cost?

    $1,240/night is a typical cost for a holiday rental in Wailea throughout the year. Rental prices do vary though, and you’ll find that November 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 $237/night. In general, any Wailea rental for $842 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 7.9/10 and 181 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).

  • Are there any Rental holiday rentals in Wailea?

    At the moment, there are 604 properties listed as a Rental holiday rental in Wailea. A popular Rental in Wailea amongst our users is Wailea Ekolu #805.

See more FAQs

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