Whether you choose a condo or villa as your Wailea vacation rental, you'll have the perfect base to explore the beauty of Maui.

Choose the perfect vacation rental
Best Vacation Home Deals in Wailea
Save up to 68%
Book a welcoming vacation rental from $105 per night by searching through the 4,601 options listed in Wailea. Using HomeToGo you can immediately compare the prices of each listed rental to find the best price and save up to 67%.
Top-Rated Rentals and Accommodations in Wailea
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Recommended Vacation Rentals in Wailea
Find your perfect vacation rental in Wailea: from $105 per night
Budget-friendly Vacation Rentals in Wailea
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Vacation rentals and apartments with air conditioning
Keep cool during your trip to Wailea and book a vacation rental with air conditioning.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Wailea rental with full kitchen.
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Wailea with their own private patios and balconies.
Popular Rental Amenities in Wailea
Above, you can find the most commonly chosen filters in Wailea and the number of rentals that have them. Wailea is the right place to book a rental if you're dreaming of days spent poolside or you want to stay cool in your vacation home, as the most common features are "Pool" and "Air conditioning." Three features that are not often provided are "Wheelchair accessible," "Fireplace," and "Sauna."
Waterfront Vacation Rentals in Wailea
Want to find a fantastic beach vacation rental in Wailea?
Apply the 'distance to water' filter while searching and discover the best beachfront homes for your trip. There is a number of accommodations in Wailea that are just a short walk from the ocean. From pet-friendly rentals by the beach to waterfront offers with jacuzzis, the ideal accommodation in Wailea is waiting - discover it now through HomeToGo.

Price and Availability Index in Wailea
Vacation Rental Price Information in Wailea
We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night in Wailea. Prices rise in February and reach an average of $819 a night (2/10 - 2/17), making it the most expensive time to book a rental in the next 12 months. Conversely, the cheapest average prices are in a week of August (8/31 - 9/7).
Rental availability information in Wailea
The availability graph shows the percentage of available rentals in Wailea. It is harder to find an accommodation during a week of September (9/7 - 9/14), as 84% of the rentals are booked. It will be easy to find a rental that suits you in a week of June (6/22 - 6/29), as 79% of the rentals are still available.
The Weather in Wailea
Above are the weather conditions for Wailea. August is the warmest month of the year in Wailea with temperatures reaching a maximum average of 90°. Conversely, January is the coolest month in Wailea, with temperatures going under 63° The rainiest month is March while the driest month is January.
7-Day Weather Forecast in Wailea
Accommodations for your vacation in Wailea
Information about vacation rentals in Wailea
🏡 Vacation rentals available | 4,601 homes |
---|---|
💳 Possible discounts | up to 67% |
🌙 Nightly prices starting at | $105 |
⭐ Popular amenities | Pool, Air conditioning and Kitchen |
🏊 Vacation rentals with pools | 4,075 homes |
Frequently Asked Questions
What is the average price per night for a vacation home in Wailea?
The price of a night's stay in Wailea starts at $105. If you would like to stay in a apartment rental, the average price is $654 per night. A house rental Wailea will cost $1,518 per night on average.
How many vacation homes are available for booking in Wailea?
There are 4,601 vacation rentals available for booking for your trip.
What amenities are most popular for vacation rentals in Wailea?
Travelers look for Pool, Air conditioning, and Kitchen when booking a vacation rental in Wailea.
How many vacation rentals with a pool are in Wailea?
Wailea has 4,075 Condo and Apartment rental options available for booking.
Are dogs allowed in vacation homes in Wailea?
Absolutely, currently there are 41 rentals in Wailea that allow dogs and the average cost is $2,343 per night.
What are the best months to travel to Wailea?
August and September are typically the warmest months in Wailea with temperatures around 90 °F. January and February in Wailea are the coldest, with 63 °F on average.
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