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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 March ($430). Conversely, the most expensive month to stay in Wailea is April ($1,057).

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

The cheapest day to stay in Wailea is Saturday ($435). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,133.

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 $197 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 $316 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 14 December 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.
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
$316
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
$409
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
$410
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
$651
Avg. per night
View Deal
Makena Surf- Coraltree Residence Collect
Makena Surf- Coraltree Residence Collect

Makena Surf- Coraltree Residence Collect

Wailea, Maui, HI, United States
3.4 km from city centre
Air conditioning
$685
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
$795
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 14 December 2025. The average price for a hotel in Wailea is $638/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
$607
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
$1,703
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
$776
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
$409
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 14 December 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 14 December 2025.

  • How much does a holiday rental in Wailea cost?

    The average cost for a holiday rental in Wailea is $638/night. A good holiday rental deal in Wailea would be for $514/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.

  • What is the best Wailea holiday rental?

    Palms at Wailea Maui has a 8.4 rating from 181 users, making it the best Wailea holiday rental based on our data.

  • 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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