South Maui Homes & Cottages

The region of South Maui is situated on the island’s southern coastline with spectacular Mount Haleakala in the background and the sunken volcanic crater of Molokini offshore. The South Maui communities of Wailea, Makena, and Kihei offer the perfect setting for Maui vacation rental homes and cottages. Make your home base here, and you’ll have access to wonderful beaches, world-class golf courses, and a wide variety of shops, restaurants, and attractions. All vacation rentals on our site are operating with the required Maui County permits.

Coral Gardens Estate at Makena Bay

 South Maui

 Up to 8	king_bed 4
 Starts at $4300	bathtub 4

One of the most striking four-bedroom four-bath luxury vacation homes on Maui, Coral Gardens Estate at Makena Bay...

Moana Hideaway

 South Maui

 Up to 8	king_bed 3-4
 Starts at $2695	bathtub 3-4

Moana Hideaway includes both a 3-bedroom/3-bath main house and a free-standing traditional-style cottage home with an...

Dreams Come True on Maui

 South Maui

 Up to 4	king_bed 1
 Starts at $135	bathtub 1

We welcome you to discover "Aloha" here at Dreams Come True on Maui Bed and Breakfast and Cottage rental in South Maui....

Wailea Sunset Bungalow

 South Maui

 Up to 4	king_bed 2
 Starts at $1395	bathtub 1

Wailea Sunset Bungalow is a charming 2-bedroom, 1-bath oceanfront vacation home nestled between two stunning sandy...

Wailea Sunset Estate

 South Maui

 Up to 10	king_bed 4
 Starts at $4650	bathtub 5.5

Wailea Sunset Estate is a beautiful 4,400-square-foot modern luxury estate with four bedrooms and five and a half...

Mango Surf Beachfront Villa

 South Maui

 Up to 6	king_bed 3
 Starts at $2500	bathtub 2

Mango Surf Beachfront Villa is a 3-bedroom luxury beach house in Kihei, Maui. Private pool, cabana house, gourmet kitchen and more. Legally permitted.