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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 ($358). Conversely, the most expensive month to stay in Wailea is June ($2,074).

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

The cheapest day to stay in Wailea is Tuesday ($512). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,707.

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

Save money by booking a vacation rental at least 16 days before your trip to Wailea. The lowest price found when booking 16 days ahead was $193 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 $289 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 28 January 2026
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
$289
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
$360
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
$500
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
Spa
$591
Avg. per night
View Deal
Polo Beach Club
Polo Beach Club

Polo Beach Club

Wailea, Maui, HI, United States
1.7 km from city centre
Air conditioning
Airport shuttle
$765
Avg. per night
View Deal
Makena Surf- Coraltree Residence Collection
Makena Surf- Coraltree Residence Collection

Makena Surf- Coraltree Residence Collection

Wailea, Maui, HI, United States
3.4 km from city centre
Air conditioning
$786
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,270 hotels in Wailea and price data was last updated on 28 January 2026. The average price for a hotel in Wailea is $953/night.
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
$426
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
$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 28 January 2026.
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 28 January 2026.

  • How much does a holiday rental in Wailea cost?

    The average cost for a holiday rental in Wailea is $954/night. A good holiday rental deal in Wailea would be for $785/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 8.2 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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