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.

Shambala Tropical Estate

Shambala Tropical Estate is a secluded and very private six bedroom, 11,000-square-foot enclave on 2 acres perched on a gentle slope overlooking Wailea Resort, Kihei Town and the sunny coastline of South Maui. Double-gated...See More →

Rates from: $6500  

Guests: Up to 12

Bedrooms: Up to 6

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: $1695  

Guests: Up to 8

Bedrooms: Up to 4

MauiHouse4Rent

Great for large families or couples traveling together! Our MauiHouse4Rent Kihei vacation home is a 5-bedroom 3-bath house, beautifully decorated in cozy Hawaiian beach style decor with all the amenities and comforts of home. Featuring two full...See More →

Rates from: $550   - $ 1100

Guests: Up to 10

Bedrooms: Up to 5

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: $2700  

Guests: Up to 8

Bedrooms: Up to 4

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: $115  

Guests: Up to 4

Bedrooms: Up to 1

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: $995  

Guests: Up to 4

Bedrooms: Up to 2

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: $1650  

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: $1700  

Guests: Up to 6

Bedrooms: Up to 3

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: $2600  

Guests: Up to 8

Bedrooms: Up to 4

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