I’m going to be candid about my love affair with Hawaii. We live in the Pacific Northwest and when winter rolls around, we find ourselves desperate for a quick, sunny getaway and Hawaii is just a direct flight away. Maui is our island of choice because of its beautiful beaches, family-friendly luxury resorts, and consistent nice weather. Over the years, we’ve fallen in love with Wailea, located on the south shore of Maui, and have found it worth the splurge for the family who wants to relax in style. Below you’ll find three of our family’s favorite hotels in Wailea.

Favorite hotel pool: Grand Wailea

Those families seeking pool time will find the best pool on Maui at the Grand Wailea. With a meandering maze of waterslides, a lazy river, baby sand beach pool, rope swing, and hidden hot tubs, my kids beg us to visit the Grand Wailea each year so they can spend their days splashing in the pool until the sun goes down.

Favorite beachfront property: Fairmont Kea Lani

On our last two visits to Maui, our family has chosen to spend part of our trip at the Fairmont Kea Lani. We love the property’s all suite one-bedroom units and easy access to Polo Beach. We spent our mornings by the pool and afternoons lounging on the sand with our picnic lunch, while the little ones built sandcastles and older kids hit the gentle waves for boogie boarding. Can aloha get any sweeter?

Best condo to share: Ho’olei

Viewfinder Tip: Like to spread out a little? Book the Ho’olei for extra room. 

One of our best trips to Maui was when we shared a three-bedroom townhome at Ho’olei in Wailea. The homes in this gated community can be pricey, but split with another family, we were able to trade up to a gorgeous property that offered lots of space for us to co-exist and enjoy BBQ meals together on the spacious lanai. Some of the units even offer special access rights to The Grand Wailea pool, making it the best of both worlds for families looking to combine condo and hotel perks.

What do you look for when booking accommodations?