What to expect: Avid golfers, vacationing families, and extended-stay travelers frequent these privately owned condominiums on Paipu Beach. Although it’s 5 minutes away from the bustling resorts and Shops at Wailea, the gated apartment community feels less crowded and more residential. Buildings were built in 1983 and 1993, and landscaping along walking trails from parking lots to individual units includes hibiscus, bird of paradise, red ginger, and fragrant plumeria trees.

Amenity highlights: The white-sand Paipu Beach is inviting for snorkeling, swimming, or relaxing. Makena Surf’s condos are in a key-accessible, security-patrolled gated community. Grounds include two swimming pools, two spa tubs, and barbecue areas. Four free oceanfront tennis courts feature complimentary clinics seasonally. Other seasonal complimentary activities include manager’s poolside parties and water aerobics.

Insider tip: Grocery delivery and private catering are available locally as a break from shopping and cooking.

What to expect: Sand-colored stucco, aqua awnings, and hillside gardens create a serene Mediterranean ambience at the 10-acre Outrigger Palms. A half-mile from Wailea's shops and beach, the condominium resort is within three miles of downtown Kihei and Wailea Golf Club.

Amenity highlights: A large, whale-shaped pool with spa tub and lounge chairs is nestled in a tropical landscape with a meandering stream. Complimentary wireless Internet access is available in a breezy, island-style lobby.

Insider tip: Four miles south over a narrowing road, Makena Beach State Park has the expansive, white-sand Big Beach, 1.5 miles long and more than 100 feet wide.

What to expect: Dense, lush tropical plants and flowers surround two- and three-story buildings, which are arrayed on a natural hillside. These gardens create privacy screens so guests enjoy peace and quiet without any sense of the community's size. With no hotel services, no manager, and no front desk, Grand Champions is focused on home-away-from-home living, rather than resort living.

Amenity highlights: Two pool complexes with sundecks, spa tubs, barbecue grills, restrooms, and showers constitute the community's amenities, just enough for enjoyment but not enough to disturb rest and relaxation.

Insider tip: A mile north of the resort, a large, uncrowded stretch of sand called Keawakapu Beach satisfies guests' Hawaiian-vacation dreams. Adjacent to the neighboring resort is a public parking lot. Signs point to the beach, which offers great snorkeling, terrific boogie boarding, and long tropical-fantasy walks.