Insights
Cheapest hotels
Where to stay

Vacation rentals in Wailea

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

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

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 November ($333). Conversely, the most expensive month to stay in Wailea is April ($938).

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

The cheapest day to stay in Wailea is Wednesday ($406). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $1,154.

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.
Find deals

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 $201 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 14 September 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.
Maui Banyan Vacation Club
Maui Banyan Vacation Club

Maui Banyan Vacation Club

Kīhei, Maui, HI, United States
5.5 km from city centre
Air conditioning
$201
Avg. per night
View Deal

Other accommodations in Wailea

Find the perfect holiday rental for your stay in Wailea. There are 1,525 hotels in Wailea and price data was last updated on 14 September 2025. The average price for a hotel in Wailea is $601/night.
Hotel Wailea
Hotel Wailea

Hotel Wailea

555 Kaukahi Street, Wailea, Maui, HI, United States
1.6 km from city centre
Free Wi-Fi
$798
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
0.3 km from city centre
Free Wi-Fi
$481
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 September 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 September 2025.

  • How much does a holiday rental in Wailea cost?

    The average cost for a holiday rental in Wailea is $602/night. A good holiday rental deal in Wailea would be for $489/night or less. The cheapest rental deal found recently by our users was $82/night. If you’re flexible with your travel dates, then try to avoid booking April, the most expensive month of the year. Booking November is the cheapest month to book a holiday rental in Wailea.

  • Are there any Resort holiday rentals in Wailea?

    Yes, there are 8 Resort holiday rentals in Wailea. According to our data, Grand Wailea, A Waldorf Astoria Resort is currently the most popular Resort rental in the city.

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. Discover hotel discounts now and make your hotel reservation today.