Wailea houses

Take your pick of 152 holiday home rentals in Wailea. Whether you’re planning to stay in Halama Street or another well-known neighbourhood, we’ll help you find the perfect home away from home.

Prices vary depending on the time of year, length of stay and property location, so enter your travel details to browse what’s available. No matter your budget or plans, Vrbo has holiday home rentals in Wailea suited to guests of every type.

It can all depend on the type of weather you prefer, among other considerations. Many people visiting Kihei get a Wailea holiday home rental in August, when the average temperature ranges from 25ºC (77ºF) to 27ºC (81ºF).

When searching for your holiday home rental in Wailea, take advantage of our “Location” filter. This lets you narrow down the sorts of areas you want to stay in, whether that’s around nature or somewhere close to the action.

Browse our weekend rentals and prepare for an exciting couple of days away. Our top tips for booking your perfect house in Wailea? Stay flexible when searching and modify your travel dates until you find the holiday home rental that suits your style.

If you want to experience Wailea with your beloved pet at your side, use our convenient filter tool to browse pet-friendly houses. Check the “Pets allowed” box to find a holiday home rental with welcome touches like fenced-in yards and complimentary treats. Because when the family goes away, the pets should share in the adventure!

Planning an unforgettable trip to Wailea means discovering fun things that the whole family will love. Wailea Beach, Maui Ocean Centre and Kamaole Beach Park are only the start of the options here. And Vrbo’s holiday home rentals are the ideal base for your sightseeing pursuits.

From houses set along lakeshores to those in busy downtown areas, Vrbo has a wide variety of holiday home rentals to pick from. One of the best things about booking with us? You won’t have to share your space with any other guests. Plus, with our One Key™ rewards programme, you can earn OneKeyCash™* and spend it on eligible bookings across Vrbo. And with flexible cancellation policies and support throughout your getaway, we’ll ensure everything goes smoothly. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.