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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 ($336). Conversely, the most expensive month to stay in Wailea is June ($1,163).

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

The cheapest day to stay in Wailea is Saturday ($366). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,068.

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

Save money by booking a vacation rental at least 10 days before your trip to Wailea. The lowest price found when booking 10 days ahead was $219 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 $196 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 31 July 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.
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
$196
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,526 hotels in Wailea and price data was last updated on 31 July 2025. The average price for a hotel in Wailea is $672/night.
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
$350
Avg. per night
View Deal
Polo Beach Club - Coraltree Residence Collection
Polo Beach Club - Coraltree Residence Collection

Polo Beach Club - Coraltree Residence Collection

34 Wailea Gateway Center Suite A102, Wailea, Maui, HI, United States
1.7 km from city centre
Free Wi-Fi
Parking
Airport shuttle
$731
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
Free Wi-Fi
Parking
$1,247
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
$894
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
$476
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 31 July 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 31 July 2025.

  • How much does a holiday rental in Wailea cost?

    The average cost for a holiday rental in Wailea is $673/night. A good holiday rental deal in Wailea would be for $533/night or less. The cheapest rental deal found recently by our users was $163/night. If you’re flexible with your travel dates, then try to avoid booking June, the most expensive month of the year. Booking July 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.

Find better results for your stay in Wailea

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