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Vacation rentals in Wailea

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Travel insights for vacation rentals in Wailea

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Wailea.

What is the cheapest month to book a vacation rental in Wailea?

The cheapest month to book a vacation rental in Wailea is October ($374). Conversely, the most expensive month to stay in Wailea is December ($1,120).

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

The cheapest day to stay in Wailea is Sunday ($478). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,053.

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 vacation 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 May 12, 2025
These are the lowest prices we've found on vacation rentals in Wailea at the moment. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Show all 1,472 vacation rentals
Maui Banyan Vacation Club
Maui Banyan Vacation Club

Maui Banyan Vacation Club

Kīhei, Maui, HI, United States
3.4 mi from city centre
Air Conditioning
$243
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,472 hotels in Wailea and price data was last updated on May 12, 2025. The average price for a hotel in Wailea is $631/night.
Show all 1,472 stays
Palms at Wailea Maui
Palms at Wailea Maui

Palms at Wailea Maui

3200 Wailea Alanui Dr, Wailea, Maui, HI, United States
0.6 mi from city centre
Free Wi-Fi
Parking
$459
Avg. per night
View Deal
Wailea Beach Villas
Wailea Beach Villas

Wailea Beach Villas

3800 Wailea Alanui Drive, Wailea, Maui, HI, United States
0.4 mi from city centre
Free Wi-Fi
Parking
$1,528
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
0.6 mi from city centre
$2,308
Avg. per night
View Deal
Mana Kai Maui
Mana Kai Maui

Mana Kai Maui

2960 S. Kihei Road, Wailea, Maui, HI, United States
1.1 mi from city centre
$368
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
0.3 mi from city centre
$1,108
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

Wailea, Maui, HI, United States
0.1 mi from city centre
Air Conditioning
$327
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
0.4 mi from city centre
$382
Avg. per night
View Deal
Hotel Wailea
Hotel Wailea

Hotel Wailea

555 Kaukahi Street, Wailea, Maui, HI, United States
1.0 mi from city centre
Free Wi-Fi
$859
Avg. per night
View Deal

Where to stay in Wailea

Explore different neighborhoods and areas within Wailea to find the perfect location for your stay. Map data was last updated on May 12, 2025.
Scroll to and zoom in on the areas in Wailea you plan on visiting to find nearby properties. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

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 May 12, 2025.

  • How much does a vacation rental in Wailea cost?

    $632 per night is how much a vacation rental in Wailea costs, on average. $176 per night was the cheapest price recently found by our users, though anything for $568 per night or less is a good deal. Keep in mind that Wailea vacation rental prices fluctuate throughout the year: the most expensive month to book is April, and the cheapest time to book is November.

  • Are there any Resort vacation rentals in Wailea?

    At the moment, there are 8 properties listed as a Resort vacation rental in Wailea. A popular Resort in Wailea amongst our users is Four Seasons Resort Maui At Wailea.

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