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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 March ($646). Conversely, the most expensive month to stay in Wailea is April ($1,590).

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

The cheapest day to stay in Wailea is Saturday ($654). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,705.

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 $296 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 $476 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 8 December 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.
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
$476
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
$531
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
$563
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
$975
Avg. per night
View Deal
Makena Surf
Makena Surf

Makena Surf

Wailea, Maui, HI, United States
3.4 km from city centre
Air conditioning
$995
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
$1,144
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,254 hotels in Wailea and price data was last updated on 8 December 2025. The average price for a hotel in Wailea is $960/night.
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
$1,144
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
$563
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 8 December 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 8 December 2025.

  • How much does a holiday rental in Wailea cost?

    $961 per night is how much a holiday rental in Wailea costs, on average. $210 per night was the cheapest price recently found by our users, though anything for $773 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 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 8.4/10 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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