Beachfront Wailea Rentals

Maui Vacation Accommodation prices quoted in this guide are subject to the 17.962% Hawaii State "Hotel and Accommodations" Tax.

Maui Condo Rental Collection

If you’re looking for a less expensive alternative to the major hotels but still want to enjoy the sunnier side of Maui, we recommend staying in a condominium in Kihei or Wailea on the southshore. Since it is only 15 - 25 minutes from the northshore and the westside, this is a good central location on the island. There are many restaurants and shopping options around town as well as many of the islands’ best beaches. There is also excellent golf and tennis available in the world-class resort of Wailea. The snorkeling is ideal throughout Kihei and Wailea. Most condominiums have full kitchens and private balconies as well as swimming pools and barbecue areas in most complexes. Ma'alaea Harbor is just a short drive away and offers snorkeling trips to Molokini as well as whale/dolphin-watching cruises. Stunning sunsets are a year-round experience on the southshore.

More helpful information: Maui's Southshore

Southshore of Maui vs. the Westside of Maui

Maui's Southshore - Why is it a better choice vs. the westside?

We've been asked this question for many years and it will continue to be a good one, especially given the amount of "false info" out on the internet these days, with all sorts of "reviews" being written and taken as "truth". Both of these sides of Maui have been developed for "tourism" by virtue of their geographical location, though the westside was developed first, mostly in the 70's and 80's because of the prior existence of Lahaina town, with the southshore being a little later to develop in the 80's and 90's.

Here's our opinion, along with some facts, about the southshore of Maui vs. the westside, based again on 15+ years of not only living here but guest feedback during all that time:

1) The southshore typically has warmer and drier weather thru the critical "winter/spring" months of December thru April. While both are "leeward" shores, the westside gets about the same rainfall and wind conditions as the northshore. The southshore tends to be much less rainy and even less windy the further south you go.

2) The beaches , all of which are open to the public, including the ones in Wailea where the hotels are located, are superior not only in number but they could be called more "user-friendly" in that they are less prone to get surf most of the year and provide better swimming, walking, and snorkeling given their geographical location on the island. The Wailea beach path , is a poplular walking path for exploring the beautiful white sand beaches in the Wailea area.

3) It's more centrally located so that you can use it as a good "home base" from which to enjoy the whole island, which is really what a vacation on Maui is all about, without being somewhat "isolated" as you would be staying on the westside. It's just a 15- 30 minute drive to the northshore and 30 - 45 minutes to the westside, depending on where you're staying on the southshore.

4) There's less "density" of development on the southshore in terms of condos, hotels, and commercialized areas. Of course, no one is attracted to the "suburban sprawl" of the southshore, that's not what you come to Maui for, but it is nice to have modern conveniences of shops and restaurants close by without having to "look" at them or be surrounded by them during your stay, which is why we only recommend properties in the northern end or southern ends of the southshore, not in mid-town Kihei, so that the busiest parts are "out of sight/out of mind".

5) The sunsets are better. (OK, that's not true, sunsets here are wonderful just about everywhere.)