How much does a vacation rental in Wailea cost?

$978 per night is how much a vacation rental in Wailea costs, on average. $212 per night was the cheapest price recently found by our users, though anything for $676 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 July, and the cheapest time to book is May.

What is the best Wailea vacation rental?

Palms at Wailea Maui has a 7.9 rating from 181 users, making it the best Wailea vacation rental based on our data.

What’s the closest vacation rental to Kahului Airport?

It’s only 13.8 mi from Kahului Airport to Palms at Wailea Maui (the nearest Wailea vacation rental to the airport).

Are there any Resort vacation rentals in Wailea?

At the moment, there are 13 properties listed as a Resort vacation rental in Wailea. A popular Resort in Wailea amongst our users is Grand Wailea, A Waldorf Astoria Resort.

Wailea Vacation Rentals, Apartments & Condos

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 May ($259). Conversely, the most expensive month to stay in Wailea is July ($2,320).

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

The cheapest day to stay in Wailea is Saturday ($501). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,687.

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

Save money by booking a vacation rental at least 80 days before your trip to Wailea. The lowest price found when booking 80 days ahead was $200 per night.

Find deals

Cheapest vacation rentals in Wailea, Hawaii

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 1,285 vacation rentals

Palms at Wailea Maui

Wailea, Maui, HI, United States

0.6 mi from city centre

Air Conditioning

$331

Avg. per night

View Deal

Wailea Grand Champions - Maui Condo & Home

155 Wailea Ike Place, Wailea, Maui, HI, United States

0.1 mi from city centre

Free Wi-Fi

$376

Avg. per night

View Deal

Wailea Elua Village - Coraltree Residence Collection

Wailea, Maui, HI, United States

0.2 mi from city centre

Air Conditioning

$588

Avg. per night

View Deal

Other accommodations in Wailea

Show all 1,285 stays

Palms at Wailea Maui

Wailea, Maui, HI, United States

0.6 mi from city centre

Air Conditioning

$331

Avg. per night

View Deal

Grand Wailea, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Wailea, Maui, HI, United States

0.4 mi from city centre

$683

Avg. per night

View Deal

Andaz Maui at Wailea Resort

3550 Wailea Alanui Drive, Wailea, Maui, HI, United States

0.3 mi from city centre

$785

Avg. per night

View Deal

Ho olei at Grand Wailea

146 Ho'Olei Circle, Wailea, Maui, HI, United States

0.6 mi from city centre

Parking

$1,992

Avg. per night

View Deal

Wailea Grand Champions - Maui Condo & Home

155 Wailea Ike Place, Wailea, Maui, HI, United States

0.1 mi from city centre

Free Wi-Fi

$376

Avg. per night

View Deal

Fairmont Kea Lani, Maui

4100 Wailea Alanui Drive, Wailea, Maui, HI, United States

1.0 mi from city centre

Free Wi-Fi

$1,018

Avg. per night

View Deal

Where to stay in Wailea

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

How much does a vacation rental in Wailea cost?
$978 per night is how much a vacation rental in Wailea costs, on average. $212 per night was the cheapest price recently found by our users, though anything for $676 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 July, and the cheapest time to book is May.
What is the best Wailea vacation rental?
Palms at Wailea Maui has a 7.9 rating from 181 users, making it the best Wailea vacation rental based on our data.
What’s the closest vacation rental to Kahului Airport?
It’s only 13.8 mi from Kahului Airport to Palms at Wailea Maui (the nearest Wailea vacation rental to the airport).
Are there any Resort vacation rentals in Wailea?
At the moment, there are 13 properties listed as a Resort vacation rental in Wailea. A popular Resort in Wailea amongst our users is Grand Wailea, A Waldorf Astoria Resort.

See more FAQs

Find better results for your stay in Wailea

Hotels in Hawaii

Travel insights for vacation rentals 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 May ($259). Conversely, the most expensive month to stay in Wailea is July ($2,320).

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

The cheapest day to stay in Wailea is Saturday ($501). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,687.

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

Save money by booking a vacation rental at least 80 days before your trip to Wailea. The lowest price found when booking 80 days ahead was $200 per night.

Cheapest vacation rentals in Wailea, Hawaii

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.

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,285 hotels in Wailea and price data was last updated on September 6, 2026. The average price for a hotel in Wailea is $855/night.

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 September 6, 2026.

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

How much does a vacation rental in Wailea cost?

What is the best Wailea vacation rental?

What’s the closest vacation rental to Kahului Airport?

Are there any Resort vacation rentals in Wailea?

Find better results for your stay in Wailea

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Popular vacation destinations in Hawaii

Find vacation rentals in popular Hawaii cities that fit your unique needs

Vacation rentals in Wailea

Search and compare Wailea, HI vacation rentals from hundreds of travel sites on HotelsCombined and save.

Travel insights for vacation rentals 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 May ($259). Conversely, the most expensive month to stay in Wailea is July ($2,320).

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

The cheapest day to stay in Wailea is Saturday ($501). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,687.

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

Save money by booking a vacation rental at least 80 days before your trip to Wailea. The lowest price found when booking 80 days ahead was $200 per night.

Cheapest vacation rentals in Wailea, Hawaii

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.

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,285 hotels in Wailea and price data was last updated on September 6, 2026. The average price for a hotel in Wailea is $855/night.

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 September 6, 2026.

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

How much does a vacation rental in Wailea cost?

What is the best Wailea vacation rental?

What’s the closest vacation rental to Kahului Airport?

Are there any Resort vacation rentals in Wailea?

Find better results for your stay in Wailea

Explore these cities in Hawaii

Looking to explore Hawaii during your trip? These are other popular cities nearby that HotelsCombined users visit

Visit Top Destinations

These destinations around the world are some of the most sought after locations from our users

Cities our users search for

Based on the last 12 months of user searches on HotelsCombined

Popular vacation destinations in Hawaii

Find vacation rentals in popular Hawaii cities that fit your unique needs