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Holiday hires 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 ($651). Conversely, the most expensive month to stay in Wailea is November ($1,860).

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

The cheapest day to stay in Wailea is Tuesday ($662). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $1,954.

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 $266 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 $497 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 10 March 2026
For those on a budget, these are the cheapest holiday rentals available in Wailea for the selected dates. If you have the flexibility, change the dates selected to compare prices.
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
$497
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
$521
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
$544
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
$800
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
$977
Avg. per night
View Deal
Makena Surf
Makena Surf

Makena Surf

Wailea, Maui, HI, United States
3.4 km from city centre
Air conditioning
$982
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,267 hotels in Wailea and price data was last updated on 10 March 2026. The average price for a hotel in Wailea is $1,012/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
$1,075
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
$2,644
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
$1,286
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
$680
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
$497
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 10 March 2026.
Navigate to the areas in Wailea you plan to visit to find holiday rentals that are close by. More information on a given vacation rental can be accessed by clicking the holiday rental's name within the map.

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 10 March 2026.

  • How much does a holiday rental in Wailea cost?

    $1,012 per night is how much a holiday rental in Wailea costs, on average. $199 per night was the cheapest price recently found by our users, though anything for $702 per night or less is a good deal. Keep in mind that Wailea holiday rental prices fluctuate throughout the year: the most expensive month to book is November, and the cheapest time to book is October.

  • What is the best Wailea holiday rental?

    The best holiday rental in Wailea is Palms at Wailea Maui, according to our user data. 180 users from HotelsCombined gave the Palms at Wailea Maui a 7.9/10 rating.

  • 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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