This condo complex with Mediterranean-style stucco buildings, red-tile roofs, and three-stories-tall arches marks the border between Kihei and Wailea—an excellent launching pad for your vacation. Managed by the respected Aqua Aston chain, Maui Hill combines the amenities of a hotel—24-hour front desk, concierge, pool, hot tub, tennis courts, putting green, and more—with the convenience of a condo (and no resort or cleaning fees!). Units are spacious, with ample kitchens, air-conditioning (welcome in this climate), washer/dryers, queen-size sofa beds, and roomy lanais—most with ocean views. (For prime views, seek out units #35 and #36.) Two of South Maui’s best beaches are across the street; restaurants, shops, and golf courses are nearby. Check the website for significant discounts.