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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 ($673). Conversely, the most expensive month to stay in Wailea is April ($1,397).

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

The cheapest day to stay in Wailea is Saturday ($621). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,755.

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 $291 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 $689 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 24 ottobre 2025
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
$689
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
$1,316
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,232 hotels in Wailea and price data was last updated on 24 ottobre 2025. The average price for a hotel in Wailea is $905/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
$2,779
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
$1,176
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
$1,320
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
$420
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
$689
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
Airport shuttle
$1,493
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 ottobre 2025.
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 24 ottobre 2025.

  • How much does a holiday rental in Wailea cost?

    $906 per night is how much a holiday rental in Wailea costs, on average. $215 per night was the cheapest price recently found by our users, though anything for $704 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 April, and the cheapest time to book is October.

  • 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 Polo Beach Club - Coraltree Residence Collection holiday rental. This holiday apartment is just 24.9 km away from the Wailea airport.

  • Are there any Resort holiday rentals in Wailea?

    If you’re looking to book a Resort holiday rental in Wailea, then you have 8 to choose from. We recommend looking at Grand Wailea, A Waldorf Astoria Resort as it’s currently the most popular Resort rental among our users.

Find better results for your stay in Wailea

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $77 and Hotels Under $154. Discover hotel discounts now and make your hotel reservation today.