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Vacation rentals 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 October ($379). Conversely, the most expensive month to stay in Wailea is December ($1,188).

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

The cheapest day to stay in Wailea is Saturday ($536). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $1,019.

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

Save money by booking a vacation rental at least 9 days before your trip to Wailea. The lowest price found when booking 9 days ahead was $211 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 $243 per night. There is currently one property in Wailea that can be booked for this price. Maui Banyan Vacation Club is one of the hotels that can be booked for the lowest price in Wailea. Price data was last updated on 15 June 2025
Out of the vacation rentals in Wailea we've come across, these properties are priced the lowest. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
Show all 1,498 holiday rentals
Maui Banyan Vacation Club
Maui Banyan Vacation Club

Maui Banyan Vacation Club

Kīhei, Maui, HI, United States
5.5 km from city centre
Air conditioning
$243
Avg. per night
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Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,498 hotels in Wailea and price data was last updated on 15 June 2025. The average price for a hotel in Wailea is $722/night.
Show all 1,498 stays
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
$491
Avg. per night
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Wailea Grand Champions Villas - Coraltree Residence Collection
Wailea Grand Champions Villas - Coraltree Residence Collection

Wailea Grand Champions Villas - Coraltree Residence Collection

Wailea, Maui, HI, United States
0.2 km from city centre
Air conditioning
$327
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
1.0 km from city centre
Free Wi-Fi
Parking
$459
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 15 June 2025.
Utilize the map to find properties close to the Wailea area(s) or attractions you plan on visiting. As an added benefit, users can click a vacation rental they're interesting in to find helpful information and deals for that vacation rental.

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 15 June 2025.

  • How much does a holiday rental in Wailea cost?

    The average cost for a holiday rental in Wailea is $722/night. A good holiday rental deal in Wailea would be for $560/night or less. The cheapest rental deal found recently by our users was $172/night. If you’re flexible with your travel dates, then try to avoid booking June, the most expensive month of the year. Booking June is the cheapest month to book a holiday rental in Wailea.

  • Are there any Resort holiday rentals in Wailea?

    Yes, there are 8 Resort holiday rentals in Wailea. According to our data, Four Seasons Resort Maui At Wailea is currently the most popular Resort rental in the city.

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