Why stay in a condo when you can feel at home in one of these two beautifully updated, vintage cottages? They’re shaded by mature mango trees on a 1-acre lot and lie within a short walk to swimmable Keawakapu Beach (and close to Wailea’s 1.5-mile beach path)—so take advantage of the complimentary beach chairs, coolers, and boogie boards. Both cottages have fully equipped kitchens, washer-dryers, air-conditioning, three parking spaces, and decks with tables, chairs, and barbecues; kids can run around the large yard while parents make dinner or drink their morning coffee. Cottage 1 is great for families, with one king bedroom and another with three twin beds, a great room, office, and bathroom with island-style private outdoor shower. Plantation-style Cottage 2 is ideal for two couples or larger families, offering two king bedrooms and one with two twin beds, living room, and 1.5 small but modern baths. Friendly owners Charlie and Yvonne, who have three boys of their own, chose furnishings with just the right mix of comfort and sturdiness, with fun marine- and beach-themed prints serving as colorful accents to soft pastel walls and neutral upholstery. Note: The website will direct you to VRBO for booking; that platform charges a varying service fee tied to the room rate plus a refundable damage deposit of $295.