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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 May ($438). Conversely, the most expensive month to stay in Wailea is June ($859).

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

The cheapest day to stay in Wailea is Saturday ($404). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,142.

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 $189 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 $448 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 29 October 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.
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
$448
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
$864
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
$1,001
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,256 hotels in Wailea and price data was last updated on 29 October 2025. The average price for a hotel in Wailea is $609/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
$616
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
$1,807
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
$781
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
$294
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
$1,001
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
$360
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 29 October 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 29 October 2025.

  • How much does a holiday rental in Wailea cost?

    The average cost for a holiday rental in Wailea is $609/night. A good holiday rental deal in Wailea would be for $454/night or less. The cheapest rental deal found recently by our users was $140/night. If you’re flexible with your travel dates, then try to avoid booking April, the most expensive month of the year. Booking October 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, Grand Wailea, A Waldorf Astoria Resort is currently the most popular Resort rental in the city.

Find better results for your stay in Wailea

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