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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 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 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 $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 October 29, 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.
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
0.1 mi from city centre
Free Wi-Fi
$448
Avg. per night
View Deal
Elua Village
Elua Village

Elua Village

Wailea, Maui, HI, United States
0.1 mi 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
1.1 mi from city centre
Air Conditioning
Airport shuttle
$1,001
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect vacation rental for your stay in Wailea. There are 1,256 hotels in Wailea and price data was last updated on October 29, 2025. The average price for a hotel in Wailea is $619/night.
Makena Surf- Coraltree Residence Collection
Makena Surf- Coraltree Residence Collection

Makena Surf- Coraltree Residence Collection

4850 Makena Alanui, Wailea, Maui, HI, United States
2.1 mi from city centre
$1,271
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
0.2 mi from city centre
Free Wi-Fi
$360
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
$971
Avg. per night
View Deal
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
0.5 mi 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
0.6 mi from city centre
$1,802
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
$780
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 October 29, 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 October 29, 2025.

  • How much does a vacation rental in Wailea cost?

    $620 per night is how much a vacation rental in Wailea costs, on average. $140 per night was the cheapest price recently found by our users, though anything for $465 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 October.

  • What’s the closest vacation rental to Kahului Airport?

    It’s only 14.4 mi from Kahului Airport to Wailea Grand Champions Villas - Coraltree Residence Collection (the nearest Wailea vacation rental to the airport).

  • 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 Grand Wailea, A Waldorf Astoria Resort.

Find better results for your stay in Wailea

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly, including Hotels Under $50 and Hotels Under $100. Discover hotel discounts now and make your hotel reservation today.