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.

Dreams Come True on Maui

We welcome you to discover "Aloha" here at Dreams Come True on Maui Bed and Breakfast and Cottage rental in South Maui. We offer two bed and breakfast suites--each with private entrance, private bath...See More →

Rates from: $135  

Guests: Up to 4

Bedrooms: Up to 1

Wailea Sunset Estate

Wailea Sunset Estate is a beautiful 4,400-square-foot modern luxury estate with four bedrooms and five and a half bathrooms. The home has a stunning panoramic ocean front setting. A sprawling manicured lawn slopes down...See More →

Rates from: $3925  

Guests: Up to 10

Bedrooms: Up to 4

Moana Hideaway

Moana Hideaway includes both a 3-bedroom/3-bath main house and a free-standing traditional-style cottage home with an additional 1-bedroom/1-bath for a total 4-bedroom/4- bath accommodation. Here you will find intimate luxury with an elegant beach...See More →

Rates from: $2650  

Guests: Up to 8

Bedrooms: Up to 4

Mango Surf Beachfront Villa

Mango Surf Beachfront Villa offers intimate luxury with an elegant beach house ambiance on a half-acre property with gated back yard, sumptuous pool area, and a sprawling emerald green lawn that reaches to the...See More →

Rates from: $2500  

Guests: Up to 6

Bedrooms: Up to 3

Kamaole Villa

Location, location, location! Kamaole Villa is a favorite amongst our guests who have stayed elsewhere on the island. Let go of your stress here in this lovely, lavish home on one of the best...See More →

Rates from: $1800  

Guests: Up to 6

Bedrooms: Up to 3

Coral Gardens Estate at Makena Bay

One of the most striking four-bedroom four-bath luxury vacation homes on Maui, Coral Gardens Estate at Makena Bay features breathtaking panoramic ocean views from its expansive open-air great room as well as from three...See More →

Rates from: $3000  

Guests: Up to 8

Bedrooms: Up to 4

Wailea Sunset Bungalow

The Wailea Sunset Bungalow is a little slice of heaven on earth in a prime location nestled between two sandy swimming beaches along one of Maui’s most sought-after stretches of coast. This vintage 2-bedroom,...See More →

Rates from: $1450  

Guests: Up to 4

Bedrooms: Up to 2

Sapphire Seas Beach Estate

A rare gem, Sapphire Seas offers the ideal Maui luxury escape ─ seamless indoor-outdoor living on a flowering half-acre and privacy-gated property set back on the ocean side of a quiet residential street, yet...See More →

Rates from: $3395  

Guests: Up to 8

Bedrooms: Up to 4

Hale Napua Maui

Hale Napua Maui is a lovely 4-bedroom private home in Kihei, newly permitted for vacation rentals. Our South Maui rental home accommodates up to eight guests, providing  2,400 square feet of living space. Hale...See More →

Rates from: $545  

Guests: Up to 8

Bedrooms: Up to 4

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