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About South Maui/Southshore Vacation Rental Homes.
The second largest of Hawaii’s stunning eight islands, Maui is a mouth-watering, exotic resort with plenty to see and do throughout your stay. Similarly if a quiet, restful vacation rental is your preferred choice, then this too can be arranged.
The beautiful Southshore of Maui boasts two or three charming destinations. The town of Kihei is both well located and functional, one of the hottest places to stay in Maui as it avoids the breeze in comparison to other parts of the island and has a selection of holiday villas to choose from.
Sprawling coastline and dramatic scenery can be found south of Kihei in Wailea - a luxury resort with plenty of holiday villas and vacation rentals and trendy entertainment on offer. Take a stroll along the Wailea Beach Walk, with its stretching coastline providing the ideal viewing spot for whales.

Featured Vacation Rentals

South Maui/Southshore Vacation Rentals
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99 Rentals found
Beds: 2
Baths: 2
Sleeps: 4-5
Privacy in Paradise!
Surrounded by 3 fairways on "Old Blue Golf Course" with Golf, Ocean and Volcano Views.
$190
Day
Beds: 1
Baths: 1
Sleeps: 2-2
MAUI--Direct Oceanfront-- 1Bd/1Ba.Nice!.
DIRECT OCEANFRONT CONDO 1 Bdr/1 Bath.Upscale fully furnished, panoramic views.FREE HiSpeed Internet,Views!
$118
Day
Beds: 5
Baths: 2
Sleeps: 10-10
5 Bd Home Newly Remodeled Great Location
Maui Vacation Home, Great Location, Walk to beach, shops & restaurants. All the amenties of home provided.
$300
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Luxury Ocean View - Remodeled, Updated
Wailea Ekahi, on Keawakapu Beach, surrounded by world class golf courses - close to fabulous dining & shopping
$195
Day
Beds: 2
Baths: 2
Sleeps: 6-6
Condo Rental
Waiohului Beach Hale A101, Gorgeous 2 bedroom, 2 bath, Oceanview, Beach Front Condo.
$165
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Kamaole Sands, Kihei HI
Beautiful ocean view condo in Kihei, South Maui(Short Walking Distance to Food, Shopping and the Beach.)
$125
Day
Beds: 2
Baths: 2
Sleeps: 4-4
Ocean Views Every Room "Penthouse" A402
This is the top floor Penthouse in the front Ocean Facing building with.... 'Ocean Views from Every Room'
$135
Day
Beds: 1
Baths: 1
Sleeps: 4-4
Vacation on the Gold Coast of South Maui
Fully furnished condo across the street from Kamaole Beach Park I in South Maui. Everything you need!
$75
Day
Beds: 1
Baths: 2
Sleeps: 4-4
Five star Luxury
The condo stands apart from all others. Just remodeled from top to bottom. Everything new and upgraded.
$945
Week
Beds: 2
Baths: 2
Sleeps: 4-6
Prime beach front apartment
Bright and relaxing 2 bedroom beachfront apartment
$295
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Owner direct Maui Vista condo #3-217
Owner direct renting of our Maui condominium is always affordable, and saves you money for the many activities
$70
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Kamaole Sands resort, views, Inner Court
Our condo #1-204 at the Kamaole Sands resort is on the INNER COURTYARD with beautiful views; Bldg #1 unit #204
$125
Day
Beds: 5
Baths: 3
Sleeps: 12-14
Honuhula Island Retreat
Honuhula Island Retreat House has 5 bedrooms 3 full bathrooms, sleeping accommodations for up to 12 people.
$395
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Kihei Beach
Beach Front Condominium
$1,120
Week
Beds: 1
Baths: 1
Sleeps: 1-4
Deluxe Maui Condo
A superior water front location at a great rate, close enough to feel the spray and sleep to the sounds of the waves
$125
Day
Beds: 2
Baths: 2
Sleeps: 4-6
Prime Beach front
Beautiful 2 bedroom beach front apartment
$295
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Kamaole Sands ~ Best Rates!
Splendid 1 or 2 bedroom condos with full kitchen, washer/dryer and an ideal location.
$128
Day
Beds: 2
Baths: 2
Sleeps: 4-8
Affordable Luxury in Wailea
2 Bedroom Luxury condo in the best location on Maui.
$220
Day
Beds: 1
Baths: 1
Sleeps: 2-2
Ocean view Kihei Kai Nani condo
Remodeled super condo with pool and ocean view, unit #246 in Kihei Kai Nani
$95
Day
Beds: 1
Baths: 2
Sleeps: 2-4
Ekahi Village, Wailea
Perfect Ekahi unit, quality renovation just completed! Air conditioning installed. Sleeps 4 with 2 full baths.
$275
Day
Beds: 3
Baths: 3
Sleeps: 6-2
Private Home Rental
Quiet area in small cul-de-sac. 5 minute walk to the beach.approx. 2 blocks. Immaculately clean house.
$400
Day
Beds: 2
Baths: 3
Sleeps: 1-6
Wailele Beach Home-Maui
Oceanfront 2B, 3 B home that will sleep up to 6 guests. Sandy beach and wonderful sunsets.
$4,200
Week
Beds: 1
Baths: 2
Sleeps: 2-4
Beautiful Ground Floor Condo! No Stairs!
Beautiful Ground Floor Unit Across from Beach - No Stairs! Kamaole Sands, Kihei, Hawaii Vacation Rental
$125
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Hono Kai Resort ,Maalaea Bay
Quiet, private ground level beachfront condo with fenced patio, steps from 5 mile long Sugar Beach
$145
Day
Beds: 1
Baths: 1
Sleeps: 2-4
Maui Island Hideaway Oceanfront
Our Island Hideaway is located in the beautiful Maalaea Banyans, Maalaea, Maui, about 75 ft. from the ocean.
$145
Day


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